Older Women - Anna Part 1
When I was 28, the internet was beginning to be put into widespread use. My job took me to Chicago and I met Anna in an on line chat room. Anna lived in Malibu, California and worked for a law firm. We talked on the phone that first night, learning about each other. She has a very sexy voice, and she thought I did as well. We had both been drinking and, of course, the subject turned to sex. The next night I asked if she had a dildo or vibrator and we talked each other to orgasm. I sent her a picture of myself and she found me attractive. The next day she went to a professional photographer to get pictures of herself that she could send to me. Anna called me on the phone and told me to log on to my computer so I could see the pictures of her. She has dirty blonde hair, looked to be of Italian decent, and had a very sexy demeanor. I knew she was older than me, but not that old. The last picture she sent was one of her topless, wearing just her bikini bottoms. Wow! The way that those big melons hung off her chest turned me on. We started to make plans to get together, and it was then that she told me she was 44. Damn, I would have said she looked 30 maybe 32. Her age didn’t deter me. I ended up flying to LAX, we spent a night at her place. All I can say is that she is really good in bed. I had barely set down my suitcase in her bedroom, and she had her top off and was pulling down my pants. She gives good, enthusiastic head. I pushed her on the bed and got her pants off. I spread her legs and all I wanted to do was suck on her pussy and get her off. It didn’t take too long and when she caught her breath, she said, “Where in the fuck did you learn to do that? You just gave me one hell of an orgasm!” We did not get any sleep that night, we just could not stop fucking. Every time Anna went down on me, she rammed her cunt with the dildo, which turned me on. Anna rubbed my cock all over her face and her tits, especially her sensitive nipples. She loved how much I could cum. She loved the taste of it and I gave her a lot. We had to be at the airport at 6am the next morning. We were on our way to Acapulco to a hotel that she had stayed at regularly over the years and they knew her well. Anna guaranteed me a good time. Little did I know that we just got started.
Our adrenaline kept us going. We were drinking on the plane all the way there, acting like we were on spring break. We in the hotel by noon, it is pretty exclusive. Adults only. There were only 12 rooms in the place, all of them luxury suites. The first thing we did is pick up where we left off. Anna was all over me, and she is a moaner when she fucks. And vocal, sometimes being vulgar, and she seems to know exactly what to say at the right time because it would always increase my horniness. I’m sure the hotel could hear her calling out my name. We lasted maybe an hour, then we crashed pretty hard, totally spent. I woke up about 7pm and went in the shower which was big enough to fit 5 or 6 people. Anna walked right in and joined me, and we made sure each other was clean, some places more than others. I loved soaping up those big tits of hers. They were perfect to me. Just a little sag, which gave them a nice bounce when she moved, and she knows how to use them. Anna told me she was glad that they turned me on. Her areola are a darker red and love to be sucked on, and they shrink up a little when excited. I could’ve spent the rest of our time there soaping them up over and over.
We went to the lounge with Anna wearing a dress that left little to the imagination, very low-cut, no bra, and maximum exposure. Surprisingly, neither of us had an appetite, so we ordered appetizers. It was a Monday night and there was a single woman at the bar. She was Mexican and had a knock-out body. Even Anna made favorable comments of her. At one point saying, “She reminds me of someone, but that was a long time ago.” There was a young couple in the back making out like crazy which made Anna and I kind of laugh, but it also made us wish we were in our 20’s. They left, grabbing at each other and not caring who may be watching, Anna and I agreed it kind of made us horny. Then the owner came in, noticed Anna, and came right over to us. Edwin was from Connecticut and had owned this place for 25 years. Then his wife Carol showed up and joined us. They were in their 40’s, but they held their age as well as Anna. They were a very happy couple and I could tell that they have been around the block once or twice. It seemed they had adopted the good life here in Mexico and were loving it. Carol was attractive, she had a distinctive, professional look about her but at the same time she had a hippie chick demeanor. She also had a rack as nice as Anna’s. I noticed that Carol was constantly looking at me and smiling, like she approved of me being with Anna. We had several drinks and a delightful conversation with them until they left us. Then Anna suggested that we go to the pool for a swim. I thought we would go back to the room and get our swimming suits, but Anna said, “No, clothes are optional. Remember, this is an adults only place. Let’s go get naked!”
The pool was private and overlooking the Pacific Ocean. We took off our clothes and got in the pool. Once again Anna was all over me. In water up to our chests, Anna reached for my cock and quickly got me hard. She wrapped her legs around me and grabbed me behind the head, then lowered her pussy down on my hard on. She kissed me and we stayed in that position, just slowly moving around, talking dirty to each other. Then she picked up the pace, one of her hands went to her clit, and the moaning began. In 5 minutes she had an orgasm and fell limp in my arms. I carried her out of the pool and lay her down on a lounge chair. I lay next to her, and she exclaimed, “Fuck, this is more sex than I’ve had in years! Damn, am I ever glad I met you!” We laid back and relaxed, holding hands, and staring at an almost full moon over the ocean. I loved that we were nude, outside, and it felt like we had the place all to ourselves.
Then the Mexican woman that was at the bar appeared. She was wearing a bikini that showed off her fantastic body and sat down across the pool from us. We didn’t even try to cover ourselves up, and it was like we were showing ourselves off to her. She sat her things down and took off her tiny bikini. We squeezed each other’s hand in approval and Anna said, “She’s hot! I like her tits!” The woman put down her bag and towel, and then took off her bikini. I said to Anna, “You picked the right hotel! I like this place!” Anna laughed while the woman just looked at us. She was sitting in a chair and spread her legs, almost as if she was showing off her pussy to us. Then her hand went between her legs and she started to rub her twat. She watched us stare back at her. Anna said, “Ok, this is turning me on. I hope she doesn’t stop.” She didn’t. My cock was rising again. The woman noticed. I put my hand on Anna’s lap, and she pulled it to her pussy while played with my rising cock.. I said, “Well shit, let’s see where this goes.” Anna replied, “I was hoping you’d say that.” The woman smiled at us in approval and rubbed one of her big boobs while going a little faster on her pussy. Anna was now stroking me as I stuck a finger inside her. The woman reached in her bag and pulled out a vibrator and turned it on. We could hear the buzzing. She put it on one nipple, then the other and I could see how hard they were. She didn’t stop there. Leering at us intently, she rubbed it on her clit for a minute or so, then put it in. She took it back out and put it in her mouth, sucking her wetness off it. Still looking at us, she made a hand gesture that she wanted to come over to us. Anna nodded yes and motioned her to come over. Both of watched her get up and walk around the pool, the vibrator still in her hand. Anna said, “You ok with this?” I replied, “Can you feel how hard I am?” She said, “Good, I always wanted a man who would do this with me. It’s been a long time since I’ve been with another woman. I’ve always wanted to do a threesome, with the right people that is. And I think It’s about to happen” As the woman neared us, looking as sexy as ever with those big boobs shaking across her chest, I said, “Anna, you’re going to make my dream come true.” She gave my cock a big squeeze, then let go. Anna stood up to meet her. She said, “I’m Anna, this is Jay.” The woman introduced herself, “My name is Carlita. My room is next to yours and I can hear you. Just like a few moments ago here in the pool. I saw you in the bar, and I had to find out.” Carlita spoke fluent English. Anna reached for her hand pulling her. Anna said to her, “It’s been a long time for me to do this, but I find you incredibly sexy.” Anna kissed Carlita, Carlita kissed her back. I got up and put my arms around them. Carlita broke the kiss and smile at me, then leaned her head forward until our mouths met. I felt her tits while Anna and Carlita were rubbing each other’s cunts. Carlita’s other hand grabbed on to my cock and she said, “Anna is a lucky woman.” I said, “Let’s take this back to the room.” Carlita said, “I’ll be at your room in 2 minutes!”
I don’t know why we put our clothes back on. There was absolutely no one else in the hotel that would have seen us. Anna and I got to our room, got naked, and left the door open for Carlita. Anna kissed me and said, “I am so horny right now. Carlita reminds of a woman from a long time ago. I’m ready to play!” Anna sat me on the sofa, fed her tits to my wide open mouth saying, “Oh yeah baby. Rub my pussy and get me wet.” I took her direction well. Then she said, “I want Carlita to walk in here and catch me sucking your cock!” Anna went down on me, slowly taking as much of my cock as she could. When Carlita walked through the door, completely naked and carrying that same bag, she smiled and closed the door behind her. Carlita sat down beside me and watched Anna while rubbing her hands all over my chest. She said, “Jay, you have a nice cock, I knew you would. Hey Anna, do you want to share that with me?” Anna looked up and said, “Go for it. Wait until he eats you pussy, you’re going to love it!” Carlita took her place and with a totally different technique than Anna, making my cock have an out of this world experience. I let her suck me for about 5 minutes, Anna was watching with all of her interest, and then I had to tell Carlita to stop because I didn’t want to cum yet. I said, “Why don’t you two go in the bedroom and get to know each other better. I’ll be there in a little while.” Anna just kissed me wildly, then grabbed Carlita’s hand. They were giggling and laughing all the way until I heard those moans again.
I went to the kitchenette and got a couple of those little bottles of scotch that I would have to pay for later. I dumped them into a glass of ice and by this time my cock had gone flaccid. Yet it never looked larger to me in my life. I had to pinch myself, I was having the time of my life with an older woman again, and she is as liberal as I am. This was the best vacation of my life. I could hear the girls talking once in a while, but I couldn’t make out exactly what they said. I mindlessly played with myself and felt the urge to take a piss. So I headed to the bathroom, meaning I would have to go past the bed. I looked past the door, Anna and Carlita were in a 69, laying on their sides. They didn’t notice me at all and I watched them for a few moments. They were into each other’s pussy as much as they were on my cock. I don’t think I have ever been so turned on, being in the presence of two wild sexual and wanton women. I walked in to the bathroom and somehow I was able to stay soft, otherwise I would have never got the urine out of me. I then heard the unmistakable sound of Anna having another orgasm. Unfortunately, the toilet was positioned in a place that I could not see her. I sat down on the seat and waiting for Anna to finish off, and then flushed the toilet. They both knew I was there. I walked back in the bedroom, and Anna lay flat, her chest heaving up and down as she caught her breath and Carlita had her back to me, raised up on one arm, staring down at Anna. Carlita then turned around to see me, and said, “Come here, you’re next!” She laid down next to Anna, spread her legs and rubbed her pussy, and said, “I need that cock. Come here and let me suck it. I want you really hard for me.” I kneeled on the bed an put my cock right in front of her mouth. I got totally hard in about 3 seconds. I massaged her boobs and she kept rubbing her pussy, and I couldn’t take it any longer. I was between her legs and Anna grabbed my cock, aiming to it’s destination. Carlita was extremely wet, I was all the way inside of her in just a few strokes. Carlita let out a long guttural moan, and then said, “Oh fuck yes. I needed some hard dick. Fuck Jay, you fill me up. Fuck me with that big prick of yours. Make me feel like I’m getting royally fucked.” I rocked back and forth, picking up the speed. Then I don’t know what came over me, but I just started fucking her as fast as I could. Carlita was screaming yes, yes, yes. Her head was tossing side to side, her chest was completely flush, squeezing really hard on the big tits, her flesh spilling out between her fingers. She shouted out, “Oh fuck, don’t stop you mother fucker. I’m going to cum like a bitch. Gawd yes, fuck me!” There was no way that I was going to cum. I felt a power that I never had felt before, and I was going to give Carlita everything I had until she was satisfied. I pulled all the way out of her, then rammed it back home. Over and over, and Carlita said, “Oh fuck yes, that’s it. Keep it up, harder baby, harder. Jesus fucking christ I’m going to cum, I’m going to cum!” Carlita started gushing. Every other time I pulled out I could feel her squirt. I looked down between our legs, her cleat fluids were streaming out and soaking the bed. It felt so good when her warm fluids erupted out all over my cock and balls. I wanted to crawl inside of her. Anna was saying, “Wow, wow, wow! Look at that! Wow!” She had let out about 7 streams and when there wasn’t anymore coming out, I just rammed all the way in and held it there. In a moment, Carlita opened her eyes and stared at me. “Come here and kiss me you son of a bitch.” In an effort to thank me, she planted a winner on my mouth. I could feel Anna rubbing my ass with Carlita rubbing my back in circles. I had never felt anything wetter than Carlita’s pussy since. Anna said, “Fuck, you two turn me on. That was so hot. I almost came again from watching you!”
I stayed on top of Carlita, my weight resting on my elbows, and feeling her boobs pressed into my chest. When my cock finally went soft, Carlita squeezed it out of her and it made us laugh. I rolled over on my side between them. Carlita nestled her head on my shoulder and said, “Damn Jay, you were hitting my spot. No one has made me cum like that for a long time.” I looked over to Anna. She was leaning up on her arm, staring at me, smiling at me and rubbing her nipple. She said, “Hey Carlita, Jay hasn’t cum yet. We need to get him off.” Carlita had regained her composure and got up on her arm on the other side of me and was now playing with my limp penis. It didn’t stay limp for long. She said, “Yeah, Jay. It would make me very happy to see you get your rocks off. Why don’t you give us some instructions?” I was in the candy store with unlimited cash. I said, “I want you two to get up on your knees on either side of me.” Anna was kneeling to my left, Carlita on the right. I reached up and grabbed some tit. Anna’s was a little bigger and very soft, Carlita’s felt heavier and firmer. “Ok, now suck on your own tit that’s not in my hand.” That turns me on, seeing a woman to give pleasure to herself. “Now rub your own pussies.” My cock just lifted off. Then, “Look at each other in the eyes. Now let me see you kiss.” The desire on their faces was almost over whelming. They wanted to do this more than I wanted to see it. “Now switch hands, rub each other’s pussy.” As they did, I concentrated on their nipples, pinching and slightly pulling on them, rolling them around with my fingertips when they were hard. I let my hands fall and rubbed their asses. Anna has a skinny ass, and Carlita’s is more rounded. “Rub each other’s tits with your free hand.” They were enjoying this as much as me, and they were loving it that I was their audience and telling them what to do. I grabbed my cock by the shaft and started stroking. “Ok, put the head of my cock between your lips and lick it.” Their lips never parted until my head got in the way. I kept jacking off, their tongues darting all over. I thought that when I cum, this is the position that I want to be in. But I wasn’t going to cum yet. “Anna, suck on my cock, Carlita, suck on my balls.” Carlita was good at it, she had my whole scrotum in her mouth, her tongue felt like it was running figure eights around my nuts. Anna was now giving me deep throat. I think that she needed a little practice before having a 9” cock stuffed all the way down. She felt good beyond belief. Anna was so turned on, I watched her bring her hand down to her twat and she was finger fucking herself. Carlita must have sensed it, because she was soon doing the same thing. After a couple of minutes, I said, “Ok, now switch places.” Anna went all the way down on me and held herself there for a couple of seconds, then slowly dragged her lips up my shaft. She sucked on the head and let it go with a pop. Anna pulled on my balls, stretching them out, and she forcefully spit out my balls. Anna didn’t waste any time, she cupped my scrotum in the palm of her hand and that long tongue was flying all around it. Carlita gave me one of those stares, smiling as she went down on me. She was now jacking me off and sucking so good, just on the head. I let this go on for a little bit longer. Then, Carlita grabbed my hand and had me jacking myself off, her mouth firmly planted and expertly sucking on my head. I could tell that my time was coming near. Just then, Carlita lifted her head up and said, “I want to see you make yourself cum.” I replied, “OK, I’m almost ready.” Anna stopped and rose up on her knees also, they were waiting for further instructions, and their fingers we still inside their cunts. “Ok. Carlita, you just kneel there, keep fingering your pussy, and rub and suck on your tits. Anna, suck on my nipple and rub the other one. And when I say I’m going to cum, put your mouths together on the head of my cock like you were just doing. I want to see my cum spill out of your mouths and drip off your lips.” The thing that turned me on the most was the willingness to do whatever I said. By the looks on their faces, I think they liked the way I wanted to get off. Anna was tweaking my nipples and I felt it all the way to my cock. I was fisting myself slowly, looking at Carita play with herself. I grabbed on to one of Anna’s tits for dear life, picking up the speed with my other hand, and said, “Ok, Anna, rub my balls.” She took her finger out of her pussy and expertly massaged my balls. “Fuck, you’re turning me on. Damn Carlita, keep sucking on that tit. Put another finger in your pussy. I’m going to go faster so get ready.” Carlita could’ve been a porn star at that point. She knew she was getting to my psyche. “Rub my balls harder Anna, suck my nipple harder. Pinch it, harder. Oh fuck, oh fuck. Ok, I’m going to cum, here I cum!” By instinct, they hit the head of my cock with their mouths in unison. My fist was banging against their faces, I was jacking off as fast as I could. I announced, “Here it cums, here it cums!” They took all of the first three shots, then it started dripping down. I unloaded stream after stream, at least another 5 pulses, and the cum was sliding down my grip, and as the last few drips came out, Anna pushed Carlita out of the way and sucked me into oblivion. Carlita looked down at me, my cum still dripping down her chin, she kissed me full on the mouth, making me taste myself. I was in another world, out of orbit. Usually at this point, everything is so sensitive that I can’t take anymore. But I let Anna and Carlita keep going and I experienced a heightened state of sex that I never felt before. I held onto Carlita as tight as I could as she frenched my mouth. I could feel the combination of her saliva and my cum dripping down my cheeks. I still didn’t want this to end. Anna was keeping my cock hard, and she swung her leg around and stuffed it in her vagina. She was in dreamland until I finally went soft. I crawled into the fetal position, Anna and Carlita had the idea to rub their tits all over my body until I could get my senses back. It took a while.
We had sex until 4am. I came two more times. We would come up with ideas, and the best part is that whatever it was, no one objected. At one point, we were back in the living room and when I said, “Let’s just watch each other masturbate.” By this time, Carlita had her toys out. She used the vibrator, and Anna had a huge dildo. I got two little bottles of lotion from the bathroom and ended up using it all. All three of us had an orgasm on that one. Carlita was leaving in two days, Wednesday. Anna and I didn’t leave until Saturday morning. I think Anna let me and Carlita fuck as much as we wanted, which was a lot, because Carlita hadn’t had any dick for a while and Anna had me for the rest of the week. But also, Anna really liked to watch us. Just as much as I liked to watch her with Carlita. Once in a while she would tell us what to do. Of course, Carlita and I were more than happy to oblige. We slept until noon, where I woke up with morning wood. I took turns fucking one, then the other, but somehow I kept from coming because it was a new day. Carlita went back to her room while Anna and I took a shower together. We would meet up later to find a place to eat, I know I needed the nourishment.
I had dried off and was sitting on the bed, just watching Anna finish. I still could not believe that she was 45. I mean, if I had walked into a bar, I would have been after her right away. She exudes sex and had this poise about her. And oh, did I say she had world class tits! Others have come close, but not as good for my taste. Anna sat down beside me. I asked her if she was having fun and if she was ok with having sex with Carlita. She said she loved it, the way it happened, the way we were all open. She admitted that this had been a fantasy of hers for a long time. Then she told me her story. She told me that I reminded her of her deceased husband. He and Anna had planned on trying something like this, but never got around to it. And, on top of that, she had just lost her only daughter in an auto accident. She was 18 and had just graduated high school. She thanked me for bringing her out of her depression and, “Now I know I must go on, I do have a future. When I told you how old I was, I thought you would run away. I am so glad you didn’t and now I think I know why. The internet Gods brought us together.” She leaned into me, put her head on my shoulder, and she started to cry. I leaned back on the bed and held her in my arms. She put her leg over me and grabbed on to me for dear life. “Jay,” she said, “Just hold me. I need to get this out of my system.” Her sobs went into an almost hysterical wailing. I could not imagine that pain that she had gone through. I held her as tight as I could, she was clinging on to me for dear life. Her body was shaking beyond her control, I just held on tighter and wouldn’t let go until she got through this. It took 15 minutes, but when she finished she kissed me ‘the kiss’. A kiss that I will never forget. Then she looked me directly in my eyes, grabbed me by the shoulders, and said, “Jay, I will never forget about you. Don’t ever settle for anything less than you deserve, because you deserve it and one day some fine woman will be so lucky she found you.” She grabbed by my crotch, rather hard, and said, “And I get this mother fucker for the rest of the week. I’m going to make sure you never forget me!”
The three of us went to a restaurant that was close by the hotel. I had Anna on one arm, and Carlita on the other. I felt like Hugh Hefner. Other people just stared at us in envy. At dinner, Carlita commented that her puss was sore, but a good kind of sore. After the first bottle of wine, Carlita was getting loose and she told us her story. She is the same age as me, I am older by two weeks. Her mother died when she was 8. Her father brought her up paying every moment of devotion to her that he could. He was one of three principle owners of a bank located in the city of Jalisco. She told us the cartel wanted to launder money through the bank, but her dad did not want anything to do with it. The other 2 principles went along with the cartel. Carlita’s dad was killed. Carlita was devastated. Being the only daughter, she inherited 33 percent. She held out as long as she could, but once the cartel had their business flowing through the bank, she cashed in and she was set for life, and this happened 6 months ago. Then she said, “Anna, this was a favorite place of my fathers. He took me here when I was 18 and I remember seeing you here 10 years ago. You were with my Aunt Maria from Los Angeles.” Anna said, “Holy shit. I don’t fucking believe it. That was right after my husband passed away. I don’t know how to say this, but she was my first, and until now, the only woman I have ever been with.” Carlita replied, “It’s all right Anna. A year later, she seduced me. I’ve always liked women since.” Carlita looked at me, then said, “But I like the high hard one just as much!” Anna turned to me and said, “I told you she reminded me of someone. Carlita, I think I remember you back then. How is Maria doing? I’d like to talk to her.” Carlita said, “Maria was my mother’s sister. My father was having an affair with her. She was with him the night the gangsters came. She was shot and killed also. I always looked up to her, she was my idol. I miss them so much.” Then Carlita began sobbing. Anna and I went to her to tell her everything was going to be ok. Carlita said, “I know. And I know I can trust you two. Thanks for listening.” As much sorrow and grief that I heard in the last two hours, all of a sudden things were cheerful. We ordered, we ate. And we placed orders to go for tomorrow. We didn’t leave the hotel until Carlita left to go back to Jalisco.
That night and all the next day was nothing short of an all out fuck fest. I fucked Carlita, then Anna fucked Carlita. Carlita brought the rest of her sex toys, one being a strap on dildo that she used on Anna. Carlita was ramming Anna with it, hovering above her on outstretched arms. Once her arms got tired, Carlita was fucking her from behind and I positioned myself so Anna could suck my cock at the same time. I came all over Anna’s face and she loved it. Then I ate out Carlita for the first time. I got her clit off while Anna sucked on her tits, then I tongue fucked Carlita, begging her to squirt all over my face. And she did, in a very big way. My face, my hair, and the carpet below me were soaked. At one point we took a break and actually turned on the TV. Anna was sitting at one end of the sofa and I laid my head on her lap. When I looked up at her, she shoved her tits right in my face, and reached for my crotch. Carlita, who was sitting in the chair next to us, came over and got on her knees. She started sucking my cock and I got hard again. Anna kept jacking me off, my face was buried in her tits, and Carlita was doing such a good job sucking on the head of my cock. I thought it would be at least a half an hour before I could get hard again. But much to their delight, they instantly brought my cock back to life. As they worked me over, I thought they there was no way that they could make me cum, at least not after just I came 20 minutes ago. That is, until Anna started her dirty talk. “Fuck Carlita, did you see how quick he got hard again? Jay must love your mouth sucking his cock. I know I love it when he sucks my big tits. Do it Jay, keep doing it. I want to jack you off until you cum again in Carlita’s mouth. I love making you cum.” Carlita lifted her head up and said, “Yeah Jay. Right in my fucking mouth. Let me rub your balls, I bet that will make you cum.” Carlita went back down on me with that suction action all over my head. I could feel the tingling sensation in my balls, and out of nowhere I blew my wad. It was a small load, but Anna was urging me to cum and I couldn’t hold it back. Carlita said, “Jay, your cum tastes sweet, not salty at all!”
On Wednesday morning, Carlita had her bags packed and was ready to go. She had checked out of her room and was hanging with us. She had 90 minutes before she left. I was sitting next to her, sorry that she had to leave. Anna was sitting in the chair, and I said, “Anna, get up and do a strip tease for us.” Carlita and I just watched her as she shed what little clothing she had on. She came over and lifted Carlita’s dress and went down on her pussy. Carlita put her hand in my pants and discovered how hard I was. Then she positioned herself so she could suck my cock while Anna ate her out. After about 5 minutes Anna rose up and kissed Carlita full on the mouth, then said, “It was really turning me on to see you suck Jay’s big cock. It would turn me on even more to see you fuck him one more time before you left.” Anna had Carlita sit down on me in a reverse cowgirl position. She had her hands on Carlita’s thighs as she watched my cock go in and out. Then she just dove face first, licking at Carlita’s clit with that long pointed tongue. Carlita came, and when she got off me, Anna immediately sucked my cum right out of me. Anna said, “Yes! I just made you both cum!” Then Carlita and I were both licking Anna’s pussy, taking turns on her clit, and I could tell that Anna was excited. It took 20 minutes, but we made her cum too. Reluctantly, Carita put her clothes back on and it was time for her to leave. We would be in contact in the future.
Anna and I went to the beach, then to the pool, and pretty much got smashed the rest of the day. The drinks were flowing, we pretty drank non-stop. Anna was wearing a white tank top that was too small for her. She was braless and you could make out her nipples underneath the thin material. She was constantly turning me on, not only how she dressed but our main topic of conversation was about sex. Anna has an imagination as good, in some ways better, as mine. We relived our experience with Carlita, and discussed what we wanted to do for the next 3 days. After the sun set, we went back to the room. We were pretty fucked up by this time, and Anna said, “You know what would turn my on right now?” I replied, “Right now I’d do anything you want.” She said, “Good. Do you like wet t-shirts?” I said, “Anna, with that top you have on, you would win any wet t-shirt contest anywhere on the planet.” “Ok,” she said, “Hang on for a minute. I have an idea. Follow me.” She went to the bathroom and into the big shower. She sat down on the seat in the corner. “Do you like it when I rub my tits for you? You want to see a real wet t-shirt? Take your cock out and piss all over my tits. It will be such a turn on for me.” Anna took my shorts off, kissed the head and started to tickle my balls. “Jay, I’m really drunk. It would make me really happy to see your piss come out of your cock and soak me. I want to feel your hot piss all over me. Go ahead, do it. Here, all over my big tits.” My bladder was full, Anna was focused on my pee hole, and I just let it go. I had never done this before, but it was turning me on. Once her top was soaked, the her areola and the form and shape of her tits was clearly visible underneath. The best wet t-shirt I have ever seen. Then she reached for my penis and aimed it right in her face. It was going in her open mouth. When her mouth was full, she spit my urine back out at me. She said, “Here, point at my face. Soak me with it. My hair too, just like Carlita squirted all over.” Anna leaned back and literally ripped off her top, thrusting our her chest and making her face a target. Her hands were busy, scooping it up and running it into her face and tits. Then she quickly took off her pants and had me finish the rest of my piss on her pussy. When I finished, she told me to lay down in front of her. She started to piss all over my cock and balls, then pushed it out father, until it was splashing all over my face. I did the same thing that she did, once my mouth was full, I spit it back out at her. Just between her and me, making the most wonderful kind of taboo connection. Anna said, “Now I know you’ll never forget about me.” I got up and kissed her and I was hard. I started to jack off, and we broke the kiss. I spit on my cock and Anna spit on my cock. She started rubbing her pussy, and we took turns spitting all over each other’s face. It was so unnatural, that it felt natural. We were both getting off on this, and I was going to make myself cum. I put the head of my cock right against Anna’s crack. “Come on my clit Jay. I want to feel your hot cum splash on my swollen clit.” I hit the bullseye, and as Anna rubbed it into her pussy she had an orgasm too. Another first. We were just smiling at each other, we were soaked in piss and spit, our hair all wet and droplets all over us. My cum was now dripping off Anna’s cunt. Anna said. “Jay, I don’t know what got into me, but that was in-fucking-credible. Come here and kiss me.” There was that ‘kiss’ again. Then she said, ‘Let’s wash off.” She started the shower and she soaped up my cock really good and I was amazed that I got hard again so fast. Then she turned around and pressed her nice soft butt into my crotch and asked me, “Have you ever butt fucked before?” I told her no. Anna said, “Neither have I, but I’m so drunk right now that I want you to be the first to do it to me.” Anna bent over, her hands on the seat in the corner and those big tits drooping down in all their glory. I got behind her, soaped up my fingers really good, and slowly worked up a finger to the 2nd knuckle. Anna sighed under her breath and backed her ass up until my finger was all the way in. “Oh Jay, that feels good. Try putting in another finger.” A minute later I was going in and out with 2 fingers. “Yes, that’s it Jay. Not too fast yet, let my ass get used to this. I can’t wait to feel that big cock in there.” I soaped up my cock with the other hand in preparation. When her moans turned to sounds of pleasure, I took my finger out and pressed the head of my cock against her anus. I let Anna back up into me so she could take me in her ass at her own pace. Pretty soon the head was inside and Anna was grunting, bucking her hips to get more of me in. When I was halfway there, Anna yelled, “Oh fuck yes, oh my gawd! It hurts so fucking good. Damn Jay, you’re stretching my ass apart and I love it!” Anna was groaning loudly. I put a little bit more in, then a little bit more. The soap was losing it’s lubrication, so I grabbed a bottle of hair conditioner. I poured it out so it trickled down the crack of her ass, and it worked surprisingly good. Was Anna ever tight at first. Then her sphincter loosened up and I just rocked in and out of her. Anna had one hand between her legs and stuffed her fingers in her cunt. I don’t remember how long we fucked like this, but it seemed to last forever. She finally had an orgasm and her knees buckled causing me to slip all the way out. Her hole was gaping, wide open in the shape of my cock, then slowly closed up back to normal. She turned around and sat down to catch her breath. “Jay,” she said, “That was incredible. I’ve used a small vibrator in my ass before, but nothing as big as your cock. Now I know what it feels like to get ass fucked.” She looked at my shrinking cock and said, “Here, let me wash you off and get you clean again.” We ended up showering and fell asleep on the bed as the sun went down. For the first time in my life, my cock was completely spent.
When I opened my eyes, it was now sunrise. Anna was not in the bed with me. I rolled over and saw her sitting in the chair, playing with her pussy and looking as sexy as ever. She said, “Good morning lover. I hope you don’t mind me watching you. It’s turning me on.” I instinctively reached between my legs and in a very rare event, I did not have my early morning hard on. Looking at Anna, I could feel myself filling up with blood. Anna said, “Let me see you play with it. Get it hard for me Jay.” I was hard pretty quickly. Anna came over and kneeled on the bed beside me. Her legs spread and still rubbing her pussy. “Fuck, it just turns me on to watch you.” I reached up and grabbed her boob, then I said, “Lean over and rub those big beautiful tits all over my face.” She fed me one nipple, then the other. And soon she was slapping my head all over, swinging them from side to side, up and down, and around in circles. “There,” she said as she stopped, “I love it that you like to play. Get up and let’s get some coffee. Get dressed, I’ve got plans for us today.”
Over breakfast we talked about last night, reliving all the kinky things we did. Anna said, “I fantasize about that when I masturbate, but I had to be drunk to do it. I have such a sweet hangover this morning. My ass still feels a little sore. Thank you my lover for being so open to it. You made it feel so good!” I replied, “I’ve heard of people doing that king of stuff before. I never thought I would like it at all, let alone even try it. But fuck, did you ever turn me on in the shower last night!” I saw Edwin and Carol and they joined us. If this already wasn’t the best vacation already, it was about to get better. That is cumming up in part 2.
Our adrenaline kept us going. We were drinking on the plane all the way there, acting like we were on spring break. We in the hotel by noon, it is pretty exclusive. Adults only. There were only 12 rooms in the place, all of them luxury suites. The first thing we did is pick up where we left off. Anna was all over me, and she is a moaner when she fucks. And vocal, sometimes being vulgar, and she seems to know exactly what to say at the right time because it would always increase my horniness. I’m sure the hotel could hear her calling out my name. We lasted maybe an hour, then we crashed pretty hard, totally spent. I woke up about 7pm and went in the shower which was big enough to fit 5 or 6 people. Anna walked right in and joined me, and we made sure each other was clean, some places more than others. I loved soaping up those big tits of hers. They were perfect to me. Just a little sag, which gave them a nice bounce when she moved, and she knows how to use them. Anna told me she was glad that they turned me on. Her areola are a darker red and love to be sucked on, and they shrink up a little when excited. I could’ve spent the rest of our time there soaping them up over and over.
We went to the lounge with Anna wearing a dress that left little to the imagination, very low-cut, no bra, and maximum exposure. Surprisingly, neither of us had an appetite, so we ordered appetizers. It was a Monday night and there was a single woman at the bar. She was Mexican and had a knock-out body. Even Anna made favorable comments of her. At one point saying, “She reminds me of someone, but that was a long time ago.” There was a young couple in the back making out like crazy which made Anna and I kind of laugh, but it also made us wish we were in our 20’s. They left, grabbing at each other and not caring who may be watching, Anna and I agreed it kind of made us horny. Then the owner came in, noticed Anna, and came right over to us. Edwin was from Connecticut and had owned this place for 25 years. Then his wife Carol showed up and joined us. They were in their 40’s, but they held their age as well as Anna. They were a very happy couple and I could tell that they have been around the block once or twice. It seemed they had adopted the good life here in Mexico and were loving it. Carol was attractive, she had a distinctive, professional look about her but at the same time she had a hippie chick demeanor. She also had a rack as nice as Anna’s. I noticed that Carol was constantly looking at me and smiling, like she approved of me being with Anna. We had several drinks and a delightful conversation with them until they left us. Then Anna suggested that we go to the pool for a swim. I thought we would go back to the room and get our swimming suits, but Anna said, “No, clothes are optional. Remember, this is an adults only place. Let’s go get naked!”
The pool was private and overlooking the Pacific Ocean. We took off our clothes and got in the pool. Once again Anna was all over me. In water up to our chests, Anna reached for my cock and quickly got me hard. She wrapped her legs around me and grabbed me behind the head, then lowered her pussy down on my hard on. She kissed me and we stayed in that position, just slowly moving around, talking dirty to each other. Then she picked up the pace, one of her hands went to her clit, and the moaning began. In 5 minutes she had an orgasm and fell limp in my arms. I carried her out of the pool and lay her down on a lounge chair. I lay next to her, and she exclaimed, “Fuck, this is more sex than I’ve had in years! Damn, am I ever glad I met you!” We laid back and relaxed, holding hands, and staring at an almost full moon over the ocean. I loved that we were nude, outside, and it felt like we had the place all to ourselves.
Then the Mexican woman that was at the bar appeared. She was wearing a bikini that showed off her fantastic body and sat down across the pool from us. We didn’t even try to cover ourselves up, and it was like we were showing ourselves off to her. She sat her things down and took off her tiny bikini. We squeezed each other’s hand in approval and Anna said, “She’s hot! I like her tits!” The woman put down her bag and towel, and then took off her bikini. I said to Anna, “You picked the right hotel! I like this place!” Anna laughed while the woman just looked at us. She was sitting in a chair and spread her legs, almost as if she was showing off her pussy to us. Then her hand went between her legs and she started to rub her twat. She watched us stare back at her. Anna said, “Ok, this is turning me on. I hope she doesn’t stop.” She didn’t. My cock was rising again. The woman noticed. I put my hand on Anna’s lap, and she pulled it to her pussy while played with my rising cock.. I said, “Well shit, let’s see where this goes.” Anna replied, “I was hoping you’d say that.” The woman smiled at us in approval and rubbed one of her big boobs while going a little faster on her pussy. Anna was now stroking me as I stuck a finger inside her. The woman reached in her bag and pulled out a vibrator and turned it on. We could hear the buzzing. She put it on one nipple, then the other and I could see how hard they were. She didn’t stop there. Leering at us intently, she rubbed it on her clit for a minute or so, then put it in. She took it back out and put it in her mouth, sucking her wetness off it. Still looking at us, she made a hand gesture that she wanted to come over to us. Anna nodded yes and motioned her to come over. Both of watched her get up and walk around the pool, the vibrator still in her hand. Anna said, “You ok with this?” I replied, “Can you feel how hard I am?” She said, “Good, I always wanted a man who would do this with me. It’s been a long time since I’ve been with another woman. I’ve always wanted to do a threesome, with the right people that is. And I think It’s about to happen” As the woman neared us, looking as sexy as ever with those big boobs shaking across her chest, I said, “Anna, you’re going to make my dream come true.” She gave my cock a big squeeze, then let go. Anna stood up to meet her. She said, “I’m Anna, this is Jay.” The woman introduced herself, “My name is Carlita. My room is next to yours and I can hear you. Just like a few moments ago here in the pool. I saw you in the bar, and I had to find out.” Carlita spoke fluent English. Anna reached for her hand pulling her. Anna said to her, “It’s been a long time for me to do this, but I find you incredibly sexy.” Anna kissed Carlita, Carlita kissed her back. I got up and put my arms around them. Carlita broke the kiss and smile at me, then leaned her head forward until our mouths met. I felt her tits while Anna and Carlita were rubbing each other’s cunts. Carlita’s other hand grabbed on to my cock and she said, “Anna is a lucky woman.” I said, “Let’s take this back to the room.” Carlita said, “I’ll be at your room in 2 minutes!”
I don’t know why we put our clothes back on. There was absolutely no one else in the hotel that would have seen us. Anna and I got to our room, got naked, and left the door open for Carlita. Anna kissed me and said, “I am so horny right now. Carlita reminds of a woman from a long time ago. I’m ready to play!” Anna sat me on the sofa, fed her tits to my wide open mouth saying, “Oh yeah baby. Rub my pussy and get me wet.” I took her direction well. Then she said, “I want Carlita to walk in here and catch me sucking your cock!” Anna went down on me, slowly taking as much of my cock as she could. When Carlita walked through the door, completely naked and carrying that same bag, she smiled and closed the door behind her. Carlita sat down beside me and watched Anna while rubbing her hands all over my chest. She said, “Jay, you have a nice cock, I knew you would. Hey Anna, do you want to share that with me?” Anna looked up and said, “Go for it. Wait until he eats you pussy, you’re going to love it!” Carlita took her place and with a totally different technique than Anna, making my cock have an out of this world experience. I let her suck me for about 5 minutes, Anna was watching with all of her interest, and then I had to tell Carlita to stop because I didn’t want to cum yet. I said, “Why don’t you two go in the bedroom and get to know each other better. I’ll be there in a little while.” Anna just kissed me wildly, then grabbed Carlita’s hand. They were giggling and laughing all the way until I heard those moans again.
I went to the kitchenette and got a couple of those little bottles of scotch that I would have to pay for later. I dumped them into a glass of ice and by this time my cock had gone flaccid. Yet it never looked larger to me in my life. I had to pinch myself, I was having the time of my life with an older woman again, and she is as liberal as I am. This was the best vacation of my life. I could hear the girls talking once in a while, but I couldn’t make out exactly what they said. I mindlessly played with myself and felt the urge to take a piss. So I headed to the bathroom, meaning I would have to go past the bed. I looked past the door, Anna and Carlita were in a 69, laying on their sides. They didn’t notice me at all and I watched them for a few moments. They were into each other’s pussy as much as they were on my cock. I don’t think I have ever been so turned on, being in the presence of two wild sexual and wanton women. I walked in to the bathroom and somehow I was able to stay soft, otherwise I would have never got the urine out of me. I then heard the unmistakable sound of Anna having another orgasm. Unfortunately, the toilet was positioned in a place that I could not see her. I sat down on the seat and waiting for Anna to finish off, and then flushed the toilet. They both knew I was there. I walked back in the bedroom, and Anna lay flat, her chest heaving up and down as she caught her breath and Carlita had her back to me, raised up on one arm, staring down at Anna. Carlita then turned around to see me, and said, “Come here, you’re next!” She laid down next to Anna, spread her legs and rubbed her pussy, and said, “I need that cock. Come here and let me suck it. I want you really hard for me.” I kneeled on the bed an put my cock right in front of her mouth. I got totally hard in about 3 seconds. I massaged her boobs and she kept rubbing her pussy, and I couldn’t take it any longer. I was between her legs and Anna grabbed my cock, aiming to it’s destination. Carlita was extremely wet, I was all the way inside of her in just a few strokes. Carlita let out a long guttural moan, and then said, “Oh fuck yes. I needed some hard dick. Fuck Jay, you fill me up. Fuck me with that big prick of yours. Make me feel like I’m getting royally fucked.” I rocked back and forth, picking up the speed. Then I don’t know what came over me, but I just started fucking her as fast as I could. Carlita was screaming yes, yes, yes. Her head was tossing side to side, her chest was completely flush, squeezing really hard on the big tits, her flesh spilling out between her fingers. She shouted out, “Oh fuck, don’t stop you mother fucker. I’m going to cum like a bitch. Gawd yes, fuck me!” There was no way that I was going to cum. I felt a power that I never had felt before, and I was going to give Carlita everything I had until she was satisfied. I pulled all the way out of her, then rammed it back home. Over and over, and Carlita said, “Oh fuck yes, that’s it. Keep it up, harder baby, harder. Jesus fucking christ I’m going to cum, I’m going to cum!” Carlita started gushing. Every other time I pulled out I could feel her squirt. I looked down between our legs, her cleat fluids were streaming out and soaking the bed. It felt so good when her warm fluids erupted out all over my cock and balls. I wanted to crawl inside of her. Anna was saying, “Wow, wow, wow! Look at that! Wow!” She had let out about 7 streams and when there wasn’t anymore coming out, I just rammed all the way in and held it there. In a moment, Carlita opened her eyes and stared at me. “Come here and kiss me you son of a bitch.” In an effort to thank me, she planted a winner on my mouth. I could feel Anna rubbing my ass with Carlita rubbing my back in circles. I had never felt anything wetter than Carlita’s pussy since. Anna said, “Fuck, you two turn me on. That was so hot. I almost came again from watching you!”
I stayed on top of Carlita, my weight resting on my elbows, and feeling her boobs pressed into my chest. When my cock finally went soft, Carlita squeezed it out of her and it made us laugh. I rolled over on my side between them. Carlita nestled her head on my shoulder and said, “Damn Jay, you were hitting my spot. No one has made me cum like that for a long time.” I looked over to Anna. She was leaning up on her arm, staring at me, smiling at me and rubbing her nipple. She said, “Hey Carlita, Jay hasn’t cum yet. We need to get him off.” Carlita had regained her composure and got up on her arm on the other side of me and was now playing with my limp penis. It didn’t stay limp for long. She said, “Yeah, Jay. It would make me very happy to see you get your rocks off. Why don’t you give us some instructions?” I was in the candy store with unlimited cash. I said, “I want you two to get up on your knees on either side of me.” Anna was kneeling to my left, Carlita on the right. I reached up and grabbed some tit. Anna’s was a little bigger and very soft, Carlita’s felt heavier and firmer. “Ok, now suck on your own tit that’s not in my hand.” That turns me on, seeing a woman to give pleasure to herself. “Now rub your own pussies.” My cock just lifted off. Then, “Look at each other in the eyes. Now let me see you kiss.” The desire on their faces was almost over whelming. They wanted to do this more than I wanted to see it. “Now switch hands, rub each other’s pussy.” As they did, I concentrated on their nipples, pinching and slightly pulling on them, rolling them around with my fingertips when they were hard. I let my hands fall and rubbed their asses. Anna has a skinny ass, and Carlita’s is more rounded. “Rub each other’s tits with your free hand.” They were enjoying this as much as me, and they were loving it that I was their audience and telling them what to do. I grabbed my cock by the shaft and started stroking. “Ok, put the head of my cock between your lips and lick it.” Their lips never parted until my head got in the way. I kept jacking off, their tongues darting all over. I thought that when I cum, this is the position that I want to be in. But I wasn’t going to cum yet. “Anna, suck on my cock, Carlita, suck on my balls.” Carlita was good at it, she had my whole scrotum in her mouth, her tongue felt like it was running figure eights around my nuts. Anna was now giving me deep throat. I think that she needed a little practice before having a 9” cock stuffed all the way down. She felt good beyond belief. Anna was so turned on, I watched her bring her hand down to her twat and she was finger fucking herself. Carlita must have sensed it, because she was soon doing the same thing. After a couple of minutes, I said, “Ok, now switch places.” Anna went all the way down on me and held herself there for a couple of seconds, then slowly dragged her lips up my shaft. She sucked on the head and let it go with a pop. Anna pulled on my balls, stretching them out, and she forcefully spit out my balls. Anna didn’t waste any time, she cupped my scrotum in the palm of her hand and that long tongue was flying all around it. Carlita gave me one of those stares, smiling as she went down on me. She was now jacking me off and sucking so good, just on the head. I let this go on for a little bit longer. Then, Carlita grabbed my hand and had me jacking myself off, her mouth firmly planted and expertly sucking on my head. I could tell that my time was coming near. Just then, Carlita lifted her head up and said, “I want to see you make yourself cum.” I replied, “OK, I’m almost ready.” Anna stopped and rose up on her knees also, they were waiting for further instructions, and their fingers we still inside their cunts. “Ok. Carlita, you just kneel there, keep fingering your pussy, and rub and suck on your tits. Anna, suck on my nipple and rub the other one. And when I say I’m going to cum, put your mouths together on the head of my cock like you were just doing. I want to see my cum spill out of your mouths and drip off your lips.” The thing that turned me on the most was the willingness to do whatever I said. By the looks on their faces, I think they liked the way I wanted to get off. Anna was tweaking my nipples and I felt it all the way to my cock. I was fisting myself slowly, looking at Carita play with herself. I grabbed on to one of Anna’s tits for dear life, picking up the speed with my other hand, and said, “Ok, Anna, rub my balls.” She took her finger out of her pussy and expertly massaged my balls. “Fuck, you’re turning me on. Damn Carlita, keep sucking on that tit. Put another finger in your pussy. I’m going to go faster so get ready.” Carlita could’ve been a porn star at that point. She knew she was getting to my psyche. “Rub my balls harder Anna, suck my nipple harder. Pinch it, harder. Oh fuck, oh fuck. Ok, I’m going to cum, here I cum!” By instinct, they hit the head of my cock with their mouths in unison. My fist was banging against their faces, I was jacking off as fast as I could. I announced, “Here it cums, here it cums!” They took all of the first three shots, then it started dripping down. I unloaded stream after stream, at least another 5 pulses, and the cum was sliding down my grip, and as the last few drips came out, Anna pushed Carlita out of the way and sucked me into oblivion. Carlita looked down at me, my cum still dripping down her chin, she kissed me full on the mouth, making me taste myself. I was in another world, out of orbit. Usually at this point, everything is so sensitive that I can’t take anymore. But I let Anna and Carlita keep going and I experienced a heightened state of sex that I never felt before. I held onto Carlita as tight as I could as she frenched my mouth. I could feel the combination of her saliva and my cum dripping down my cheeks. I still didn’t want this to end. Anna was keeping my cock hard, and she swung her leg around and stuffed it in her vagina. She was in dreamland until I finally went soft. I crawled into the fetal position, Anna and Carlita had the idea to rub their tits all over my body until I could get my senses back. It took a while.
We had sex until 4am. I came two more times. We would come up with ideas, and the best part is that whatever it was, no one objected. At one point, we were back in the living room and when I said, “Let’s just watch each other masturbate.” By this time, Carlita had her toys out. She used the vibrator, and Anna had a huge dildo. I got two little bottles of lotion from the bathroom and ended up using it all. All three of us had an orgasm on that one. Carlita was leaving in two days, Wednesday. Anna and I didn’t leave until Saturday morning. I think Anna let me and Carlita fuck as much as we wanted, which was a lot, because Carlita hadn’t had any dick for a while and Anna had me for the rest of the week. But also, Anna really liked to watch us. Just as much as I liked to watch her with Carlita. Once in a while she would tell us what to do. Of course, Carlita and I were more than happy to oblige. We slept until noon, where I woke up with morning wood. I took turns fucking one, then the other, but somehow I kept from coming because it was a new day. Carlita went back to her room while Anna and I took a shower together. We would meet up later to find a place to eat, I know I needed the nourishment.
I had dried off and was sitting on the bed, just watching Anna finish. I still could not believe that she was 45. I mean, if I had walked into a bar, I would have been after her right away. She exudes sex and had this poise about her. And oh, did I say she had world class tits! Others have come close, but not as good for my taste. Anna sat down beside me. I asked her if she was having fun and if she was ok with having sex with Carlita. She said she loved it, the way it happened, the way we were all open. She admitted that this had been a fantasy of hers for a long time. Then she told me her story. She told me that I reminded her of her deceased husband. He and Anna had planned on trying something like this, but never got around to it. And, on top of that, she had just lost her only daughter in an auto accident. She was 18 and had just graduated high school. She thanked me for bringing her out of her depression and, “Now I know I must go on, I do have a future. When I told you how old I was, I thought you would run away. I am so glad you didn’t and now I think I know why. The internet Gods brought us together.” She leaned into me, put her head on my shoulder, and she started to cry. I leaned back on the bed and held her in my arms. She put her leg over me and grabbed on to me for dear life. “Jay,” she said, “Just hold me. I need to get this out of my system.” Her sobs went into an almost hysterical wailing. I could not imagine that pain that she had gone through. I held her as tight as I could, she was clinging on to me for dear life. Her body was shaking beyond her control, I just held on tighter and wouldn’t let go until she got through this. It took 15 minutes, but when she finished she kissed me ‘the kiss’. A kiss that I will never forget. Then she looked me directly in my eyes, grabbed me by the shoulders, and said, “Jay, I will never forget about you. Don’t ever settle for anything less than you deserve, because you deserve it and one day some fine woman will be so lucky she found you.” She grabbed by my crotch, rather hard, and said, “And I get this mother fucker for the rest of the week. I’m going to make sure you never forget me!”
The three of us went to a restaurant that was close by the hotel. I had Anna on one arm, and Carlita on the other. I felt like Hugh Hefner. Other people just stared at us in envy. At dinner, Carlita commented that her puss was sore, but a good kind of sore. After the first bottle of wine, Carlita was getting loose and she told us her story. She is the same age as me, I am older by two weeks. Her mother died when she was 8. Her father brought her up paying every moment of devotion to her that he could. He was one of three principle owners of a bank located in the city of Jalisco. She told us the cartel wanted to launder money through the bank, but her dad did not want anything to do with it. The other 2 principles went along with the cartel. Carlita’s dad was killed. Carlita was devastated. Being the only daughter, she inherited 33 percent. She held out as long as she could, but once the cartel had their business flowing through the bank, she cashed in and she was set for life, and this happened 6 months ago. Then she said, “Anna, this was a favorite place of my fathers. He took me here when I was 18 and I remember seeing you here 10 years ago. You were with my Aunt Maria from Los Angeles.” Anna said, “Holy shit. I don’t fucking believe it. That was right after my husband passed away. I don’t know how to say this, but she was my first, and until now, the only woman I have ever been with.” Carlita replied, “It’s all right Anna. A year later, she seduced me. I’ve always liked women since.” Carlita looked at me, then said, “But I like the high hard one just as much!” Anna turned to me and said, “I told you she reminded me of someone. Carlita, I think I remember you back then. How is Maria doing? I’d like to talk to her.” Carlita said, “Maria was my mother’s sister. My father was having an affair with her. She was with him the night the gangsters came. She was shot and killed also. I always looked up to her, she was my idol. I miss them so much.” Then Carlita began sobbing. Anna and I went to her to tell her everything was going to be ok. Carlita said, “I know. And I know I can trust you two. Thanks for listening.” As much sorrow and grief that I heard in the last two hours, all of a sudden things were cheerful. We ordered, we ate. And we placed orders to go for tomorrow. We didn’t leave the hotel until Carlita left to go back to Jalisco.
That night and all the next day was nothing short of an all out fuck fest. I fucked Carlita, then Anna fucked Carlita. Carlita brought the rest of her sex toys, one being a strap on dildo that she used on Anna. Carlita was ramming Anna with it, hovering above her on outstretched arms. Once her arms got tired, Carlita was fucking her from behind and I positioned myself so Anna could suck my cock at the same time. I came all over Anna’s face and she loved it. Then I ate out Carlita for the first time. I got her clit off while Anna sucked on her tits, then I tongue fucked Carlita, begging her to squirt all over my face. And she did, in a very big way. My face, my hair, and the carpet below me were soaked. At one point we took a break and actually turned on the TV. Anna was sitting at one end of the sofa and I laid my head on her lap. When I looked up at her, she shoved her tits right in my face, and reached for my crotch. Carlita, who was sitting in the chair next to us, came over and got on her knees. She started sucking my cock and I got hard again. Anna kept jacking me off, my face was buried in her tits, and Carlita was doing such a good job sucking on the head of my cock. I thought it would be at least a half an hour before I could get hard again. But much to their delight, they instantly brought my cock back to life. As they worked me over, I thought they there was no way that they could make me cum, at least not after just I came 20 minutes ago. That is, until Anna started her dirty talk. “Fuck Carlita, did you see how quick he got hard again? Jay must love your mouth sucking his cock. I know I love it when he sucks my big tits. Do it Jay, keep doing it. I want to jack you off until you cum again in Carlita’s mouth. I love making you cum.” Carlita lifted her head up and said, “Yeah Jay. Right in my fucking mouth. Let me rub your balls, I bet that will make you cum.” Carlita went back down on me with that suction action all over my head. I could feel the tingling sensation in my balls, and out of nowhere I blew my wad. It was a small load, but Anna was urging me to cum and I couldn’t hold it back. Carlita said, “Jay, your cum tastes sweet, not salty at all!”
On Wednesday morning, Carlita had her bags packed and was ready to go. She had checked out of her room and was hanging with us. She had 90 minutes before she left. I was sitting next to her, sorry that she had to leave. Anna was sitting in the chair, and I said, “Anna, get up and do a strip tease for us.” Carlita and I just watched her as she shed what little clothing she had on. She came over and lifted Carlita’s dress and went down on her pussy. Carlita put her hand in my pants and discovered how hard I was. Then she positioned herself so she could suck my cock while Anna ate her out. After about 5 minutes Anna rose up and kissed Carlita full on the mouth, then said, “It was really turning me on to see you suck Jay’s big cock. It would turn me on even more to see you fuck him one more time before you left.” Anna had Carlita sit down on me in a reverse cowgirl position. She had her hands on Carlita’s thighs as she watched my cock go in and out. Then she just dove face first, licking at Carlita’s clit with that long pointed tongue. Carlita came, and when she got off me, Anna immediately sucked my cum right out of me. Anna said, “Yes! I just made you both cum!” Then Carlita and I were both licking Anna’s pussy, taking turns on her clit, and I could tell that Anna was excited. It took 20 minutes, but we made her cum too. Reluctantly, Carita put her clothes back on and it was time for her to leave. We would be in contact in the future.
Anna and I went to the beach, then to the pool, and pretty much got smashed the rest of the day. The drinks were flowing, we pretty drank non-stop. Anna was wearing a white tank top that was too small for her. She was braless and you could make out her nipples underneath the thin material. She was constantly turning me on, not only how she dressed but our main topic of conversation was about sex. Anna has an imagination as good, in some ways better, as mine. We relived our experience with Carlita, and discussed what we wanted to do for the next 3 days. After the sun set, we went back to the room. We were pretty fucked up by this time, and Anna said, “You know what would turn my on right now?” I replied, “Right now I’d do anything you want.” She said, “Good. Do you like wet t-shirts?” I said, “Anna, with that top you have on, you would win any wet t-shirt contest anywhere on the planet.” “Ok,” she said, “Hang on for a minute. I have an idea. Follow me.” She went to the bathroom and into the big shower. She sat down on the seat in the corner. “Do you like it when I rub my tits for you? You want to see a real wet t-shirt? Take your cock out and piss all over my tits. It will be such a turn on for me.” Anna took my shorts off, kissed the head and started to tickle my balls. “Jay, I’m really drunk. It would make me really happy to see your piss come out of your cock and soak me. I want to feel your hot piss all over me. Go ahead, do it. Here, all over my big tits.” My bladder was full, Anna was focused on my pee hole, and I just let it go. I had never done this before, but it was turning me on. Once her top was soaked, the her areola and the form and shape of her tits was clearly visible underneath. The best wet t-shirt I have ever seen. Then she reached for my penis and aimed it right in her face. It was going in her open mouth. When her mouth was full, she spit my urine back out at me. She said, “Here, point at my face. Soak me with it. My hair too, just like Carlita squirted all over.” Anna leaned back and literally ripped off her top, thrusting our her chest and making her face a target. Her hands were busy, scooping it up and running it into her face and tits. Then she quickly took off her pants and had me finish the rest of my piss on her pussy. When I finished, she told me to lay down in front of her. She started to piss all over my cock and balls, then pushed it out father, until it was splashing all over my face. I did the same thing that she did, once my mouth was full, I spit it back out at her. Just between her and me, making the most wonderful kind of taboo connection. Anna said, “Now I know you’ll never forget about me.” I got up and kissed her and I was hard. I started to jack off, and we broke the kiss. I spit on my cock and Anna spit on my cock. She started rubbing her pussy, and we took turns spitting all over each other’s face. It was so unnatural, that it felt natural. We were both getting off on this, and I was going to make myself cum. I put the head of my cock right against Anna’s crack. “Come on my clit Jay. I want to feel your hot cum splash on my swollen clit.” I hit the bullseye, and as Anna rubbed it into her pussy she had an orgasm too. Another first. We were just smiling at each other, we were soaked in piss and spit, our hair all wet and droplets all over us. My cum was now dripping off Anna’s cunt. Anna said. “Jay, I don’t know what got into me, but that was in-fucking-credible. Come here and kiss me.” There was that ‘kiss’ again. Then she said, ‘Let’s wash off.” She started the shower and she soaped up my cock really good and I was amazed that I got hard again so fast. Then she turned around and pressed her nice soft butt into my crotch and asked me, “Have you ever butt fucked before?” I told her no. Anna said, “Neither have I, but I’m so drunk right now that I want you to be the first to do it to me.” Anna bent over, her hands on the seat in the corner and those big tits drooping down in all their glory. I got behind her, soaped up my fingers really good, and slowly worked up a finger to the 2nd knuckle. Anna sighed under her breath and backed her ass up until my finger was all the way in. “Oh Jay, that feels good. Try putting in another finger.” A minute later I was going in and out with 2 fingers. “Yes, that’s it Jay. Not too fast yet, let my ass get used to this. I can’t wait to feel that big cock in there.” I soaped up my cock with the other hand in preparation. When her moans turned to sounds of pleasure, I took my finger out and pressed the head of my cock against her anus. I let Anna back up into me so she could take me in her ass at her own pace. Pretty soon the head was inside and Anna was grunting, bucking her hips to get more of me in. When I was halfway there, Anna yelled, “Oh fuck yes, oh my gawd! It hurts so fucking good. Damn Jay, you’re stretching my ass apart and I love it!” Anna was groaning loudly. I put a little bit more in, then a little bit more. The soap was losing it’s lubrication, so I grabbed a bottle of hair conditioner. I poured it out so it trickled down the crack of her ass, and it worked surprisingly good. Was Anna ever tight at first. Then her sphincter loosened up and I just rocked in and out of her. Anna had one hand between her legs and stuffed her fingers in her cunt. I don’t remember how long we fucked like this, but it seemed to last forever. She finally had an orgasm and her knees buckled causing me to slip all the way out. Her hole was gaping, wide open in the shape of my cock, then slowly closed up back to normal. She turned around and sat down to catch her breath. “Jay,” she said, “That was incredible. I’ve used a small vibrator in my ass before, but nothing as big as your cock. Now I know what it feels like to get ass fucked.” She looked at my shrinking cock and said, “Here, let me wash you off and get you clean again.” We ended up showering and fell asleep on the bed as the sun went down. For the first time in my life, my cock was completely spent.
When I opened my eyes, it was now sunrise. Anna was not in the bed with me. I rolled over and saw her sitting in the chair, playing with her pussy and looking as sexy as ever. She said, “Good morning lover. I hope you don’t mind me watching you. It’s turning me on.” I instinctively reached between my legs and in a very rare event, I did not have my early morning hard on. Looking at Anna, I could feel myself filling up with blood. Anna said, “Let me see you play with it. Get it hard for me Jay.” I was hard pretty quickly. Anna came over and kneeled on the bed beside me. Her legs spread and still rubbing her pussy. “Fuck, it just turns me on to watch you.” I reached up and grabbed her boob, then I said, “Lean over and rub those big beautiful tits all over my face.” She fed me one nipple, then the other. And soon she was slapping my head all over, swinging them from side to side, up and down, and around in circles. “There,” she said as she stopped, “I love it that you like to play. Get up and let’s get some coffee. Get dressed, I’ve got plans for us today.”
Over breakfast we talked about last night, reliving all the kinky things we did. Anna said, “I fantasize about that when I masturbate, but I had to be drunk to do it. I have such a sweet hangover this morning. My ass still feels a little sore. Thank you my lover for being so open to it. You made it feel so good!” I replied, “I’ve heard of people doing that king of stuff before. I never thought I would like it at all, let alone even try it. But fuck, did you ever turn me on in the shower last night!” I saw Edwin and Carol and they joined us. If this already wasn’t the best vacation already, it was about to get better. That is cumming up in part 2.
5年前
