A Weekend Out 3

A big weekend out

After my first all male sex orgy with Frank and Jeff I was getting more used to the dance of sucking cock and taking some piss action down my throat. I was hoping and fantasizing that more crossdressing would be in my future and I liked the times I was having with Herb and Frank around their wives, it was like a total fantasy land. After I met Jeff I wondered if he too was into panties and bras like I was, it was nice to be around another boy my age, 18, although I enjoyed being the boy sissy around the older men sissies, seems that we had a sissy connection that was stronger than our age difference anyway.
I was out riding my bicycle down the back road past Frank’s house one evening, checking out the creek for a nice fishing spot. I also would at times find porn books or pictures that were thrown out from cars along the side of the road. Back then getting rid of this stuff was harder and getting it in the first place for me was impossible, so any porn “gold” was a fodder for a fine wanking session.

As I got around the curve a car was pulling up from behind me and it turned out to be Herb leaving Frank’s on his way home. He pulled up and stopped, I got in the car to chat with him since we had a pretty good relationship having spent a whole weekend sucking each other a few months ago. He was interested in how I was doing and started to feel my cock, which got pretty hard fast.
Since I was already hot looking for some porn relief I felt him up in return, feeling his nice hard cock through his pants. He discovered I was wearing panties and so was he as I found out after unzipping him. Since it was getting pretty dark I felt comfortable and decided to give him a suck and went down on him, licking him through his panties. He was a very happy camper and continued to feel my cock, reaching between my legs probing for my asshole, as I spread my legs to give him more room.
As I was sucking him he started asking me if I would want to spend another Big weekend with him and Helen and a few others. I pulled up with big eyes and said “of course, and I hope we get to play sissy again, I need to be dominated more than ever and I have been dreaming since the last time that I would love to try more stuff together.” I asked him with who and he said Frank and Sophie and Helen, and a couple more but will be a surprise.
I agreed enthusiastically that the following weekend I would get out of my house (giving an excuse) and claim I was at a friend’s house, which is not a lie. He told me to bring all my fem things, which were not a whole bunch, but I would bring them. He told me to go back to sucking as he was getting hot just talking about it, so I went back to sucking him and putting him in to the back of my mouth. His cock was so big, I loved the feel in the back of my throat.
Herb continued pulling on mine and soon enough he was gasping and calling me his sissy whore and slut, I groaned in agreement. He put his hand down my back and finding my asshole put his finger into me. I was getting pretty hot and hard and Herb started cumming into my mouth, I was thirsting for his cum, hoping to catch it all, and I did. Not swallowing I moved up and kissed him with my tongue caressing his as we shared his cum together enjoying the heady moment together. I was so hot and hard I was ready to cum without my cock even being touched only with his persistent finger up my butt. He pushed me back against the seat and went down on me and sucked my cock into his mouth. I was in heaven once again.
Then a car came down the road towards us aa Herb was down sucking my hard cock deep into his throat. I was scared as hell that they would stop but they went by slowing down only to pass without bumping. Whew! that was a close call, and my cock exploded, being triggered by all the fear factor and excitement, never before did I experience such an intense orgasm.
Herb repeated my cum sucking process and sucked all of my cum into his mouth and came up to share it with me, as we kissed and exchanged my cum. We tasted each of us together, and were in heaven once again.
Once we stopped kissing we buttoned up as I had to get going quickly since it was almost totally dark and would get in trouble if I got home after total dark. I told Herb I would go come over with Frank and Sophie on Friday night. This was a perfect plan and Herb said goodbye, I said “ I am looking forward to sucking on his wife Helen’s tits; he said he would tell her.
Friday came fast, being only 3 days away, I was so horny fantasizing about the 5 of us together again and wondering what kind of scene we were going to have. I wondered how all of this sex and multiple partners along with bisex was going to affect me in my future, turns out it really made me grow up fast and appreciate the variety of sexual possibilities. It also made me see that good relationships were most important since there would not have been any of this wild sex without the trust and love in these friends.
I wore my favorite white panties with some lace, and had on my bra under my shirt as I showed up at Frank’s with my back pack full of my fem wear, which was a pair of stockings, another set of panties, and a slip. I was hoping Helen or Sophie could dress me with more things.
I parked my bike in the barn so no one would see it and went to the house. Frank answered the door looking very fem, he had his tits under a tight fitting lacy, v-neck blouse and nice silky fem pants and heels. Sophie came in and she was dressed in a nice black dress, lace at the plunging neck line, with stockings and heels, and looked hot as well.
I still had my boy clothes on and she said you want to change and I said “Yes, got anything I could borrow, like a dress and blouse”, and she said,”let’s go to my bedroom.” She dressed me in a blue skirt, and white blouse with lacy neck and arms. You could see the bra right through the blouse which made me feel real fem.
Going back into the kitchen Frank saw me he said “You look good enough to eat”, I said “I am hoping you will you cock sucking sissy lover man.” just to get us in the mood. Sophie said “I love you guys talking dirty, my pussy is getting wet, can’t wait to see you sucking Frank, I mean Fanny. We will have plenty of food to compliment our cum sucking and piss drinking tonight as well.”
Sophie packed a small suite case with some sex toys and more lingerie while Fannie packed up some bags of food. I guessed it was a bring your own and we were certainly bringing our own and more.
I walked by Sophe and she grabbed me and kissed me, she could not wait, and she reached for my cock and then ran her hand up to my breast and felt my boobs, which made me feel like a real sissy. My cock stiffened and Fanny came around from the back of me and put his hands down my skirt and felt my panty covered cock. I was swooning from their love.
I felt Sophie’s boobs and pulled one out the top of her dress and sucked her nipple for a few minutes, Fanny pulled up my skirt and dropped down for a taste of my cock, as I spread my legs he pushed a wet finger up my butt. Wow, sex was happening fast, he sucked me hard, but we had to go.
I then said “I have to pee before we leave and Fanny said feed him some piss, so I let loose and he drank me as fast as he could, not spilling a drop. Then he came up and kissed us both giving both Sophie and me a taste of my piss. I was floating on a sex high once again. Sophie said “we have to go, Helen and Herb are waiting for us”, and off we went. Since it was dark we went in the car, Fanny and I dressed in fem and Sophie in her black dress, I could not wait to undress both of them. Fanny drove and Sophie and I were in the back seat cuddling as I felt up her juicy tits, feeling her hard nipples through her bra. I slipped my hand up her dress and felt her pussy, she was softly moaning. Fanny was telling us how hot we looked, he said “you two sluts look like a couple of whores who can’t get enough, I can’t wait to fuck you both. Sophie and I both moan in pleasure at that mental scene.
Soon enough we were at Herb’s and knocked on the door. Herb came to the door dressed in his finest fem clothes, he had on heels, black stockings, boobs, black tight fitting lacy dress, blonde wig, and makeup. Fanny and I did not have makeup yet, and Herb seeing us dressed enfem smiled deeply as his eyes twinkled.
We had 8 tits between us and he reached out to welcome us in with a kiss to each of us. He tongued me deeply and slowly, then Fanny, then Sophie, I thought we were all going to have a group kiss.
He said, “Come in, Helen is waiting for us”, we went in and it was dark, candles were lit, and I could see Helen across the room with her butt up in the air and her head down on the floor, it looked like she was stuck on the floor.
As we got closer I could see she was tied up in her lingerie, black stockings, heels, garter belt, waist cincher, black bra. Her hands were tied behind her back and legs tied to a rod holding them apart with her knees tied together. I was taken back, I had never seen such a sight, I had no idea Herb or Helen were into this kind of stuff, but they sure are, I was intrigued and excited by this as well. I used to love being tied up during Indians and cowboys with my brother, I used to get in this kind of mental zone of feeling like I wanted him to do whatever he wanted with me. Strange as it might be I was hooked on this feeling of release at some level.

We all went over to Helen and Fanny and Sophie were excited to see her being restrained. Fanny went over and kissed her, tonguing her deeply, and Sophie went over and kissed her ass then spanked her with a good whack. I never saw such behavior but Helen simply groaned with pleasure and said please do that again so Sophie let her have another whack.
Helen asked me to give her a whach, so I reluctantly tapped her butt, she said, “harder, I need to be spanked harder Please hit me as hard as you can at least 5-6 times with a build-up”, so I did, with the rest cheering me on, and Helen groaning in pleasure and pain, so then I hit her real hard for the last one and she then cried out, “ouch, you got me you little sissy”, so I hit her harder again and she loved it. I was kind of jealous of her having all this attention as well and thought “wonder if I can get tied up and beaten a bit” only time would tell, my panty covered clit and pussy were getting excited at the thought being in this new pain and pleasure no holds barred orgy.

Suddenly there was a knock at the door, Herb went to answer, not being shy about being seen at the door dressed enfem. I heard strange voices and thought I could recognize one of them. There were two males and one female and they were younger rather than older, in their late teens or early twenties, but older than me. As they came through the door I could see Jeff, who I sucked off with Frank (Fanny) at a previous meeting at the pond, was leading the three, he was all dolled up enfem, looked like a street whore, heavy makeup, wig, heels, miniskirt, stockings and giant tits and a leash held by the girl, who was also all made up looking like a mistress in action. The other male was dress all in black, with makeup, but in male clothes, he had a chain belt, and some studs in his collar, he was introduced as Jake, and the girl as Lisa. I did not know these folks but they sure looked interesting. After spanking Helen and seeing how much she enjoyed it I thought this night is already over the top.

Fanny stood by and gave them all a kiss and a hug, curtseying to each as they came in. I could see they liked the scene already as both Jeff and Jake gave Fanny a tongue bath as they greeted each other. I thought all of us there are sort of like whore sluts that would do any thing to satisfy our a****l desires and I loved it all and was hoping to taste everyone there at some point in the weekend.
The three came in and patted Helen on the ass, then with a kiss and a tit squeeze with Jeff sliding under and sucking her nipples. Lisa gave Helen a nice smack on the ass and Helen said, “Thank you mistress, please can you give me more?” and Lisa gave Helen 5 more smacks with her hand. We all watched this scene unfold feeling our cocks though our panties.
Then Herb got down next to Helen and pulled up his skirt exposing his panty covered ass and large cock in his panties. They were acting as the submissive couple, both looking hot in their sexy lingerie. His stockings were pulled up high to his panties as well. Lisa reached into her bag and got a small paddle and gave Herb a few whacks, I could see his cock getting bigger, and so I went over, in a 69 position, and laid under him to suck his cock through his panties not wanting to make him cum too soon but wanted to taste him and make him feel good.
Fanny went to my cock and felt me up through my panties with Herb’s face there as well. They both had my cock out and they both took turns sucking my cock and kissing each other between sucks. Herb slid his hand under my butt and pushed a finger in my ass, so nice that they were both double teaming me. Then Fanny pushed a finger along side Herb’s in my asshole and one would go in while the other out, wow, was I in heaven.
I had Herbs cock in my mouth and was sucking along merrily, trying to swallow as much as I could. Lisa was rubbing Helen’s ass and smacking it every so often. She told Sophie to get down and let Helen eat her out, which Sophie did immediately spreading her legs and letting Helen eat her deeply.
This left the two new guys open to plug in to something, and as I looked up I saw that Jeff was pulling up his dress baring his cock came over and plugged Herb’s ass with it. I got an up close view since I was sucking on Herb, Jeff smacked Herb’s ass hard, making Herb bite a bit on my cock. Herb groaned in pleasure and I could feel him push into my mouth harder.
Jake took up behind Helen and was getting hard, Lisa helped him enter Helen’s ass as she backed into him, with her legs still tied to the wooden rod. I felt Jake’s balls as he fucked Helen, they were so big. Lisa fingered Helen’s pussy telling everyone to not cum but to get high on the sex, the cumming would only happen when Lisa was ready to let everyone cum. Now I got the mental picture that Lisa was our token mistress over a stable of submissives, we all loved it and she did too. I wondered if I could at least get some pissing action down my throat from Herb since cumming was not allowed yet.
We sucked for about ½ hour and were tiring of our positions, Herb’s ass was getting sore and Jeff was getting too hot, he might have cum without permission. So we pulled apart, Helen still roped on all fours, we all looked at her and Lisa told me to untie her and get her up, I did and Helen kissed and hugged me like I saved her. I squeezed her tits and patted her ass, working my hand underneath to her pussy which I probed for a bit. We were all in a state of partial undress or dress, I loved seeing us sissy men in our lingerie parading around in front of our women and men friends like it was a normal day in the park.

The seven of us went to the dinning room where Helen had prepped some food and Fanny and Sophie brought some as well. We sat around eating and talking sexy talk. Fanny asked me “how do you like our new friends, have you ever been sorry about getting involved with our group of friends?” I said, “ are you k**ding, I have had the most sexy fun times of my life, you guys and girls are great.
Where else could I be dressed in female clothes and get such a fucking and sucking from both sexes. You guys are great, love you men in those fem clothes, love to suck your clits and fuck your pussies. And ladies you are also wonderful, you make me feel very loved with your caresses and letting me feel you all over.
Hope you feel the same.” Sophie jumped in and said she was feeling the same about me and the others. The warm feelings were everywhere. Lisa piped up and said Helen had brought some cucumbers out and she thought it would be nice for all of use to plug our butt with one of them, luckily they were not giant cucumbers but reasonably sized, about 6-8” long.
Lisa started with Sophie, she said “Herb get the gel, Fanny spread her legs, Sophie bend over and pull up your dress.” Sophie did and showed us her pink asshole. “Nice asshole Sophie” Jeff remarked, “can I lick it for you?” Lisa said, “good idea Jeff”, and he was all over it with his tongue. Herb came over with the gel coated cucumber and pushed it against her waiting asshole, Sophie said “go easy on me Herb, you know I am smaller than you”.
Herb has a large ass hole from being plugged by too many things anyway. He pushed the cucumber in half way giving Sophie breathing room, then pushed it slowly in until it disappeared in her depths. You could see the end of it peaking through her open hole. Pull up your panties Sophie, said Lisa and an extra panty girdle was slipped on to keep the cucumber in place. Sophie stood up and gyrated around feeling it settle in her hole. She smiled and said, “ok I am ready who is next.” Lisa said “Fanny is next”, and we all worked to get Fanny’s hole filled, and another girdle pulled up but this one was one with a hole in the crotch for Fanny’s cock to stick through, I went and helped him get it in place, getting a taste of his cock as well.
Then came Herb, we picked the largest cucumber for him, 13” long and fat, Herb bent over and spread his cheeks, Helen lubed him up good and we all watched as this giant cucumber slipped in and then disappeared. Herb’s eyes lit up and his mouth opened as he realized he took the whole thing.
Helen then said she wanted to be next, but wanted one in her ass and one in her pussy. We all nodded in approval that this was a great idea to be double plugged. We got a big one for her butt, her asshole is big too, I guess both she and Herb are asshole buddies, and a smaller one for her pussy. We lubed and inserted and pulled on anther girdle to keep them in her. She was staring at us with an open mouth feeling the sensations and getting used to being full.
Then came Jeff, he leaned over and pulled down his panties and Jake held his head in his crotch, as Jeff sucked on Jake’scock through his panties, a moderately sized cucumber was lubed and inserted as Jeff groaned and spread his hole as far as he could, just barely making it in. Jeff winced in pain for a few minutes until he relaxed and got used to it.
Now it was my turn, I pulled my panties down, and bent over, Fanny came around to let me suck on his cock while I had my pussy filled, he was tweaking my boobs as well. I sucked him into the back of my throat and let him gag me a bit. He asked if I wanted a taste, and I knew this meant his piss, and I sucked harder, and as my ass was being filled Fanny filled my throat with some piss, which I swallowed hungrily, enjoying the pungent taste. Once he finished, the cucumber had been pushed fully inside of me, I was filled from both ends, I licked my lips and Helen came over to kiss me and grabbed a taste of Fanny’s piss.

Jake was being kind of quiet and Fanny noticed this and suggested that we all give him a group hug, but on the table, we cleared the table and put Jake on it. We took off his shirt, pants, socks, and shoes to reveal him in his lacy panties, I was glad to see he too was a sissy like the rest of us sissies, no real men in this group.
We surrounded the table and all leaned over and kissed or sucked part of his body, I leaned over and sucked his cock through his panties, Fanny got a nipple, Herb got another, Helen kissed his face and mouth, Sophie started on his feet, Jeff got his ass, and Lisa got the cucumber. We rolled him over with his face off the end of the table and Jeff went around and gave Jake his cock which Jake sucked expertly. Lisa greased the cucumber and slowly pushed into Jake’s ass, he was hurting by the sound of his groaning and wincing in pain but Lisa was not to stop, and finally after about 10 minutes the cucumber was in. This left only Lisa to be filled yet, and we wondered if she was going to be up for a double or single. We were all squirming being filled, my cock was so hard. All of us were moaning an groaning as we walked around feeling our insides being massaged by our cucumber dildos and butt plugs.
Helen came over and kissed Lisa on the lips, they exchanged tongues and Helen asked, “Lisa honey, would you like both holes filled or just one, and which one at that.” She said,“I would like only my pussy filled Helen, my ass I am saving for later, but a full pussy would put me in my mistress mode, I love my ass filled when I am being dominated by a strong person, none of which I think are in this room.”
Helen agreed and submissively returned with a greased cucumber. Lisa pulled up her dress and down her panties and Sophie went in to lick Lisa’s pussy to get it ready for being filled. Helen put the cucumber against Lisa’s pussy lips and Sophie licked her clit. Pushing in slowly Helen opened her up and slid the cucumber inside, it wanted to slip right out until we pulled up a short girdle up her legs and pushed the fanny side between her ass cheeks and up through her legs. This held the cucumber in place nicely.
Now we were all ready for the meal we had been waiting for, the food was brought out and we all sat and ate being so hungry after our sexy activity. We were all squirming in our seats feeling full from cucumbers filling our asses and cunts. I loved feeling my tits as well. I had some trouble sitting on the cucumber and Fanny and Herb and I sat next to each other, feeling each other’s cocks every so often, we were pretty hard most of the time.
This made for some interesting conversation as well. Fanny asked me” Do you like our orgy, I responded with you bet, wished it would never end, I love being submissive to Lisa with you sissies, my whole being loves to submit to her wishes and I like doing that with you too Fanny.”
Herb was mock jilted, “ you don’t like to submit to me?” I said, I do but when we are alone, it is more loving, Fanny is better in groups since he likes to show off and make me do more daring things. Herb came over and said how about we tie you up like Helen was and use your ass for a few rounds of fucking?” I was floored, this was not like Herb, now he was taking control. I said, “oh honey Herb, can I be your little slut sissy submissive please?” and Herb smiled and looked around at the others who were watching,
Helen and Sophie had their arms around each other, and Lisa and Jake and Jeff were holding each other as well. Everyone had something up their butt or pussy, we were in a sexual high, swinging the pendulum of intensity from one end to the other.

Herb brought out some rope and pulled a chair over, he pushed me down on the chair, the cucumber pushing higher into my ass. He pulled my arms around back and secured my wrists together, then tied my ankles to the chair. Fanny came over and felt my boobs which were nice sized, I was getting hard from the look of his cock in his girdle.
Lisa said, this is great, I love to see sissy men dominated, Herb I did not know you had it in you. Helen piped up, oh, yeah he has plenty in him, more than the cucumber for sure. Herb smiled and said “you will beg for more before he was done with me. This made me get harder, Fanny pulled his cock out from his panties and girdle and shoved it towards my face, and Jake came over and sucked the tip as I licked Jakes cheek and nibbled on his ear, since I could only use my mouth, being tied like this.
I started to realize I was totally submissive to anything they wanted to do to me. I was swooning with feelings of release, so free to wallow in my mental paradise. Fanny then shoved his cock into my mouth which brought me back to the present and Jake felt up Fanny’s ass and puttin a finger into his man pussy shoving the resident cucumber in further. Fanny loved this and pushed his cock harder into my mouth which made me gag a bit until I learned to swallow.
Sophie came around and put more lipstick on me, between sucks, she was brushing my long hair as well, saying that a sissy slut should look as well as act like one. I was moving in that general direction pretty fast being around these guys, I thought maybe I was either going to be gay or a transsexual, but I did like being where I was between all of them.
Herb finished tying me up and pulled his cock out to let me suck, so I was sucking Fanny and Herb, taking turns as they switched places in my mouth. Then Jeff came over and pulled out his cucumber from his ass and made me suck on it, this was a new taste test for sure. It was not so bad, kind of bitter. Then he put the cucumber on my leg and sat on it returning it to his pussy. My stockings were covered with his juices and I thought all I need now is for someone to piss on me to complete my travels through degradation ecstasy.
Lisa pulled Fanny over and pushed him down to feed him her pussy, it was running with juices and the cucumber was sticking out. She made Fanny eat the cucumber out of her pussy which he did eagerly. Then she started to piss in his face and he opened his mouth to drink her nectar. Now the party was getting pretty hot.
Jake saw this and pushed his limp cock in my mouth and said, drink slut, I have to piss, and then he was filling my throat with his tasty yellow liquid running down my cheeks and throat. Sophie came over and licked his piss off my face, she was totally into this as well. Jake pissed some in her mouth and she shared it with me splitting the piss load as we swallowed.
Herb was now hard but Lisa did not say to cum yet, Herb was begging her to let him cum but she said not yet, so he backed off and got softer. He came over and pissed in Sophie’s mouth and I lick her face off. Hmmm piss is good, so tasty, so nasty and deviant, makes me free of any limits.
My hands were getting numb from being tied so tight and I said I needed to be released. Lisa said, “hold on not yet”, and she went and got her crop. She started lightly hitting my chest moving down to my balls. One landed hard on my cock and it sprang to life getting rock hard, I thought, “what is this”, never thought that would happened. She continued to beat me getting harder and harder. Sophie pulled my dress open and moved my bra down exposing my nipples. She pinched my nipples hard then took one in her mouth and bit down. I thought I would die, but my cock continued to stay as hard as a rock. Lisa beat me more while all watched hoping I would cum disobeying Lisa’s command.
I was so into this that I started pleading with Lisa, Pplease hit me harder, please hit my cock, please make me cum, Sophie please pinch my nipples, ohhh, that is so good, I love this pain, keep hitting me.” And I thought how I was beaten by my mom for playing with matches as the ********** in me loved the bizarre feeling that my pain is causing me pleasure. Jeff came over and stuck his cock in my mouth, pissing into my throat a pint of piss, I was now quiet but Lisa beat me harder on my thighs, and cock, so hard I was getting welts from her crop.
Then as Jeff was finishing his load of piss down my thirsty throat, I came in large spurts from the scene, pain, and piss I was sucking out of this wonderful cock stuffing my mouth. My orgasm seemed to come from inside me rather than being having my cock stimulated.
Fanny watched me get hotter and he could tell since he had sucked me many times before, so he came down and caught my load in his mouth holding it until I was filled it. Then he came up and moved Jeff away, pulled Jeff’s face down to my face with his and we three shared my cum load being fed to us from Fanny’s mouth. This was the first cum of the evening and Lisa was the cause even though she did not say I could cum.
She then ordered Helen to untie me and clean me up. Helen came over and had me suck her tits while she untied me. Then she licked my face of piss and cum and we went to the shower together. The rest continued to congregate in the living room where Lisa started tie up more of our party members, this over the top party was continuing to be out there in wild mental space.

Helen and I took a shower together, she also had to piss and I got down and let her piss over me, into my mouth, but I could not drink any more piss to I simply let it run over the sides of my mouth. She thanked me for letting her piss on me, she said she is usually pissed on by Herb since she is more submissive. She soaped me up and shaved my face. She offered to shave my whole body but I did not want to get stares at school or at home and have to answer to any suspicious questions.
Once we were done, she put makeup on me and herself and then dressed me in one of her large bras, panties, stockings and garter belt. She gave me a blouse which kind of fit and a skirt, plus a pair of Herb’s high heels and a wig. She was dressed similarly and we went out to join the others.

Lisa by this time had tied everyone up, Herb to Fanny, Jeff to Jake, and Sophie by herself. Both Helen and I were amazed and turned on as well. Lisa said us two were going to be Lisa’s servants and do everything as she says, or we would be beaten like I was earlier but harder. I had no idea of what she would want us to do. I told her “I am yours mistress”, Helen also said the same and went to the floor sticking out her tongue to lick Lisa’s pussy in submission. I also got down and kissed Lisa’s feet sucking her toes. Lisa was thrilled to see her recent acquaintances were so pliable so quickly. She could tell she was in a room full of submissives.
She told me to get up and put the large butt plug into Helen’s ass, which Helen started to moan quietly in anticipation. I greased the plug and pushed it slowly into Helen’s ass. She was stretching widely to allow it to enter.
Herb and Fanny were getting hard being tied to each other. They were enjoying the show and told Lisa they thought I should be next in the lineup for butt plug treatment. Lisa said “she would decide”. She told me to plug both Herb and Fanny with two large flesh colored Doc Johnson butt plugs. Herb was fearful of being over stretched but I went over and kissed them both wiggling our tongues together like some happy puppies tasting each other. Fanny tied with Herb face to face exposed their asses which I easily reached around and stuck a finger in each butt to get them ready, they kissed each other enjoying the opening sensations.
I greased one plug and worked it into Herb’s ass as I Fanny him and felt his cock as it was getting hard and bumping their cocks together, the others were watching with lusty joy in their eyes at hopes of what they will receive. Fanny and Herb could not escape each other but their hands were not tied, so they could tweak my nipples and my cock as I stood next to them with a finger from each hand in each of their butts.
I then pushed the other butt plug into Fanny’s ass and he groaned and started kissing Herb directly across from his nose. Their tongues were entwined and I got down and lick their cocks. Lisa saw this and told me to suck them till they were very hard. I did so and she said to push the plugs into their asses and make them leak with precum. This was not so hard to do but they were also getting tired so took some time. I kept a pulsing rhythm on each of their butts which made them push their cocks into my mouth on a cycle.
Then Lisa said to pull up my dress and let Herb plug me with another plug, this was to keep me full until the final fucking scene by all the participants. Herb moaned at his butt plug pushing against his prostrate and me sucking his cock, bent over with my ass up. He moved the butt plug head around in my butt and I spread my hole open as far as possible. I thought I would split in half but finally the plug entered deeply into my ass. Tonight was my coming out party in in many ways and they wanted to make sure I was full of it and had a great memory.

Jeff and Jake were busy watching all the action and Lisa dragged Helen over to them, making her drag her big boobs across their faces, they started sucking hard on her large nipples, sending shivers down her spine to her pussy. Their cocks were getting rock being tied together having their hands tied to each other’s cock rings so they were continually feeling each other. They too were kissing each other deeply exchanging their tongues and slobbering all over each other’s necks. Helen tweaked their nipples, putting clothes pins on each of their nipples, which made them moan in pleasure/pain, they were biting and sucking each other’s tongues.

Lisa made her way to Sophie who was tied on her back on the floor and could not move. She had a dildo up her cunt and her tits were bound so her nipples were sticking up. Lisa stooped over Sophie’s face and put her butt into Sophies mouth who gobbled her ass as much as she could extending her tongue. I could hear Sophie gobbling Lisa’s ass, she loved eating ass. This reminded me of the time I spent with her and Fanny one weekend as she ate both our asses as Fanny and I kissed each other.
Sophie had punished Fanny and I when she found out that we were playing sex games in his barn. Fanny had me following his orders to lick his cock and take one suck as I drank cool aide one shot at a time. Fanny was trying to fill me full fast so I would piss in his mouth, he loved the piss games and was teaching me the pleasures as well. He was going to piss in my mouth as well. Sophie was pissed since she was not getting any of this action for herself so she had me come over that weekend and crossdress with Fanny and take orders from her.
Once we cleaned the house for her, she tied my hands behind my back, a favorite position of mine, and made me suck Fanny to get him hard, then to keep him there with only my mouth. This was hard since I liked to finger Fanny’s hole when I sucked him. Sophie did get me going with a cucumber up my butt, which was held in by the stiff girdle she made me put on earlier. I was in a funny mood with all the penetration from both ends.
She made me drink her piss out of a glass that she pissed in in between sucks on Fanny’s cock and once I was done drinking her down, she feed me Fanny’s cock and jerked him off in my mouth which I loved since I got to drink his warm salty cum. She came down and we shared some of his cum, me slathering it around her lips and tongue. Fanny was glowing with after cum and looked kind of lonely just watching so we went up and dribbled some of his cum into his mouth to make him feel included in our lustful activity, he loved this. Sophie untied me and we had a group hug, with my cock up against Fanny’s limp cock. Fanny indicated he was ready to piss and pushed Sophie down to do the job, she took a mouth full of piss then shared it with both Fanny and I, we loved her actions, my cock was starting to get so hard, especially with the cucumber in my asshole hitting my prostrate, I was ready to cum without touching anything.
After Sophie drank Fanny’s piss, she pulled the cucumber out of my ass, made me lick it, good thing I was clean back there, and said, “OK you two are done for today, no more fun activities.” I was not ready to stop, I had not cum yet, but Sophie told me that this was my punishment for not letting her be part of my get together with Fanny and I playing piss games. I protested but what could I do, so I put my street clothes back on and said my goodbye’s. Sophie remarked that I would get my just reward in due time, I guess this sex party was what she meant.

Back to the party, I was seeing Sophie become so depraved sucking Lisa it made me realize how desperate she was to jump into the no limits zone, which I loved like a true submissive to all these older folks. Being younger I had the advantage at times to go along or not, but Sophie was sure to kick in my humiliation needs, telling me how depraved I was and that I was lucky to have Fanny as such a caring mature sissy man who had deep perverted feelings about me and my swimmers body. I thought Fanny was simply being a dirty old man but I understood him as being very sensitive to my sissy feelings and knew how to make my cock hard with just his way of talking dirty to me.
Sophie was in her element sucking Lisa’s ass and pussy and she was getting Lisa to reach an orgasm and before she did she called me over so that she could kiss me hard on the mouth and grab my balls. She started to squeeze them and I thought I was going to die, she squeezed so hard. Then she came and I was over the edge with pain, then she let go, my balls were happy and felt weird like they were in another dimension. My butt plug was trying to come out and I could not tell if there was something pushing it either. Since I did not want to make a mess I went to the bath room and removed the plug. Nothing followed it out and it was clean, so I re-lubed it and pushed it back into my butt then held it up with my girdle.

By the time I got back, Lisa had untied all the men and made them get down on their knees with their asses in the air. She got Helen and Sophie to get some cucumbers and sausages from the refrig and insert them into all the men’s asses. I just got back into the room and was already full, but Lisa made me remove my butt plug, leaving me with a void.
Lisa told Helen to get the long zucchini and put the fat end in Herb’s ass and the smaller end in my ass. I sat on Herbs ass and slowly impaled my ass on this zucchini sticking out of his butt. Herb pushed back into me as I was coming down, we were getting totally stretched.
Lisa mentioned that she had to piss, and so did Helen and Sophie, seemed like it was timed. I thought here we go, nothing like a big group piss. I wondered how Lisa was going to direct this one.
She started by getting the women lined up next to each other. One man per woman with Fanny and I at each end next to the end women. Lisa was in the middle and told Helen to her left to piss into Jeff’s mouth, who must pass the piss to Fanny on the side, then Fanny to me, and me to Herb, and Herb to Jake who was at Lisa’s pussy.
Then Jake had to swallow. Then it was Jake’s turn to take a mouthful and pass it around until it got to Herb who had to swallow. We all did this passing the piss and taking turns swallowing. It was an exercise in how to carefully swap piss and spit, we were all tempted to do more exploration with our tongues but we had a harder time not swallowing the delicious piss.
Once the women were empty, the men also had to go, Lisa told Helen and Sophie to both drink our piss one man at a time, sharing the piss with the pisser, who then could swap with any other male counterpart as they chose. We were all very intoxicated with the sexual high and the release from all normal inhibitions. We all were so relaxed and into each other we collapsed on the piss covered plastic sheet on the floor and simply cuddled and held each other close in our wet clothes and exhausted bodies. We were ready for bed and only the shower stood between us and total relaxing sleep.

The next day

I woke up around 11 AM the next morning, sleeping between Herb and Helen, two of my favorites. Herb’s cock was hard pushing against my butt, pushing against my asshole. I could use a good fuck from either he or Fanny today, but I did not know what was going to happen, so I focused on kissing Helen’s boobs which were up against my face, she had her arms around me as she was sleeping along. I was hoping they would wake soon since I had a piss hard-on that needed some attention, I didn’t think we were going to be drinking piss so early, and I was right.
Herb woke up and he pulled me out to the bathroom with him. As I pissed he ran his hand through the stream and licked his fingers, and let me taste but no drinking, which was ok. We jumped into the shower together and he let me shave him from neck to toe, making him very smooth . Since I didn’t have much hair I did not need to shave, wanted to, but did not want to raise eyebrows, so I did not shave completely.
Herb was feeling my cock from behind, had his middle finger against my asshole and Helen came in sleepily from the bedroom. She asked, “What are you fem boys up to this bright and early?” which was not so early. We told her we were getting our fem bodies ready for a fem day, which she cheered upon hearing this wonderful idea. She came in the shower and held us both as she pissed on our legs, we played with her piss and tasted her nectar.
After the shower we got dry and had a group kiss Helen then directed Herb and I to dress each other in our fem finest. He put my boobs on and I did his, we pulled our slips on, mine his and his mine. We were so slippery so lovely we held each other for a moment. Then our dresses after we did our makeup. It seemed we were going to have a fem session for the whole day. We both put on our heels and Helen dressed in male attire, she had on dress pants, a shirt, and tie. Both Herb and I were interested in what was going on, Helen also had a cock bump, must have been from a strap on which she snuck in under her pants.
We went into the kitchen and all the other guys were cross dressed, every one of us had makeup, heels, dress, stockings, and boobs. The other two women were dressed as males also with that tell tale bump where their cocks are. We fem guys were making our own bumps in our dress fronts. We were bumping into each other feeling the other’s boobs just o to see how they were. Then we all set down and passed around some coffee and bagels discussing our pleasurable times from the past evening.
I told them I was so into all of them I did not want our weekend to end, they all agreed but said there will be more to come. The bois were feeling so fem they were oohing and aahing. I loved the gentle softness that filled the room, our male dressed women tried to cross roles and they were more aggressive in their language and tended to call us fucking sissies a bunch of wimpy sissies who could not get a guy to fuck them if we tried. Of course we didn’t have to try but they I thought, wonder if we could, which lead me to think about maybe I could be a whore and make some bucks sucking off some guys. Being dressed made this easier to think those thoughts.
Sophie made some remarks about giving me some punishment for not including her in my barn episode with Fanny and she pulled my arms back behind me and my boobs were sticking out like big watermelons. Fanny then reached over and felt them like they were real, Lisa said, how you do like being restrained and others feeling your boobs. I said, I love it, I love being tied up as well, since I was as young k**. Lisa told Sophie to tied me to the chair, my hands behind my back. My cock started to grow pushing against my panties.
Helen came over and gave me a kiss like a guy would and felt my tits like a guy wood. She bumped her bulge up against my face and I opened my mouth and grabbed her bulge. The other sissies were squealing approvals and hoping to get the same. Lisa being the dominate one then brought out a gag and tied my mouth open so I could only grunt.
The other sissies were starting to feel their own boobs and hardening cocks at the scene I was beginning to enjoy. Lisa told Jake to come over and feel me like I was a lovely woman, to be very soft and feminine and get me hard but not to let me cum. I was swooning with the attention.
Lisa then told Helen and Sophie to tie Fanny up next to me, gag her as well. Jeff was told to get by Fanny and make him hard, but not to let him cum. Fanny was groaning in pleasure as she got hard.
This left Herb who was told to sit on a chair and feel his tits and cock but not to cum. Now with all the sissies busy, the male she’s stood back and looked at the master piece, all the sissies giving each other pleasure in some form or another. The male she’s then gave each other kisses and felt each others strap-ons, they were giddy with pleasure to see how big they were. They were making a cock display for us sissies and what a good job they did too.

The morning turned into afternoon, I was hard as a rock, still tied with Jake’s light touching attention. He had his mouth and lips all over my cock and face. Sucking my ears, and my neck, he was feeling my tits. Fanny was still tied and gagged also, he was loving the attention so much, being hard and moaning to cum, but Lisa warned us not to cum or we would be sorry, until she told us we could.
My being was so overwhelmed by being constrained I was so ready to cum, I could cum by someone just tweaking my nipples. The male shes could see both Fanny and I were so close to cuming they told the others to untie us and make us suck those who were sucking us.
I gladly got down and sucked Jake’s cock through his panties under his dress. As I was doing this Lisa got behind Jake and lifted his dress, pulled his panties to the side and then pushed her cock up his butt pussy. He loved the fullness, and his cock got hard in my mouth, I sucked for all I was worth. Jake was gasping being so over stimulated. Fanny leaned over and gave Jake a deep kiss, taking his tong deep in this mouth, they were swallowing each others lips, biting love bites as two lovers, it was so good to hear.
Helen came over to Herb and pulled Jeff along and pushed Herb’s cock into Jeff’s mouth, then she lifted Jeff’s dress and felt his butt, slipping her fingers into his asshole one at a time, taking them out and licking each one to lube it before putting it back in. Kind of like a man tasting a woman’s pussy one finger at a time. Sophie was standing back and feeling her boobs through her boy shirt, kind of made her look strange. She was pushing the strap on into her pussy, she said she wanted to fuck herself silly with her strap -n. Lisa said, no you won’t you have to fuck Herb, he needs the relief since he did not get tied up and subdued.
I was told that I was not such a great girl and had to do more to make myself wanted by our male she’s so I begged to be fucked by the male shes specifically Lisa since she was so dominant. She told me to remove my dress and slip, I was down to my garters, stockings, bra, and panties with a hard as a rock cock.
She bent me over and filled my ass with her plastic cock, Fanny came around and fed me his cock, I sucked for all I was worth. Life was good; cock in front cock in back. I was in my own sexual heaven with all those around me. What more perversions could I achieved in my short life. I could not wait till I could go further once I moved out of my parents house. And then I came into my hand, with out even touching myself, I sucked Fanny hard and he came in my mouth, then Lisa also had a great cum. Fanny came down to share his cum from my mouth and I brought my hand up to his mouth, and we both shared our cum with Lisa who leaned in to taste. We were all one, once again.