Elaine's Panties

I have a friend who puts forth the image of the super-macho alpha male. He plays golf, hunts, watches football on TV and ogles the ladies in our social group.
His wife is a curvaceous woman who had turned my head for decades. I’d really like to get into her panties, both figuratively and literally. I have been secretly sneaking into her laundry hamper for years and pilfering her panties, nighties, bras, girdles and anything else I can snag. I take them home with me and wear them, fondle myself with them and masturbate in, on and with them. I don’t know how many gallons of semen I have squirted into her big luxurious and silky nylon lingerie.
I should have known that she would find me out and did. But she never told me for years, until one evening I excused myself and went to the upstairs bath to relieve myself. I did my usual rummaging through the hamper and came up with a couple of pairs of panties. I smelled of the gussets and rubbed them over my cock, then stuffed them in my pockets. That’s when she stepped into the room.
“How long have you been doing this, violating my things?”
I hemmed and hawed and gave it up. “I’ve been stealing your underwear for some years, now. It’s as close to the real thing as I ever figured I get,” I replied. The jig was up, and there was no use in trying to lie my way out of trouble.
“Well, frankly, it turns me on to think that you find me attractive, but what is it that attracts you? Is it the thought of doing something naughty?”
“No, I never thought about being caught. I just like your smell, and, to tell the truth, I love the feel of women’s silky garments against my skin. I love to wear your things, too, but the thought that they are touching me in places where they had touched you, and your aroma just send me over the edge.”
“I appreciate your candor, but we must figure out what we should do, now that the truth is out. Darryl is going to be out of town next week, and perhaps you and I can get to know each other a bit better.”
“I think I would like that very much.”
The next week, Elaine called me and asked me to come to her house for dinner. Darryl would be out, but we could visit, have a nice dinner and a drink. We set up the date for Thursday evening.
Thursday evening I knocked on Elaine’s door promptly at 7:00pm with flowers and a bottle of wine. She came to the door wearing a simple print dress and casual shoes. I was happy with that because I had assumed to dress casually and wore a button down shirt and slacks with loafers. She invited me to the kitchen to chat while she finished preparing seafood and a salad for supper. I opened the wine and poured us both a glass. We chatted over supper and then cleaned up and went to the lounge.
Elaine started the conversation abruptly by asking if I was wearing men’s or women’s underwear, and could she see it. I told her that I was wearing panties and stockings. Since all the cards were on the table, I stood and removed my shoes and socks, then my pants and shirt. I stood naked except for my silk stockings and my nylon brief panties. I told her that I had been wearing panties solely since she had caught me sniffing and masturbating in hers last week.
“Why do you wear them? Are you gay? Some kind of predator or something? I don’t mean to be critical. I like to know who I’m dealing with. Tell me about it.”
I figured there was no sense lying, so I just came right and told her that since age eleven or twelve I had been using and, when I could, wearing my sister’s and my mother’s panties, slips and silky nightgowns. I liked wearing my sister’s best because she was closer to my size. But when I masturbated with the silky nylon I liked my mother’s best because they were larger and more luxurious. There was a period while I was in the service that I didn’t indulge my fetish, but other than that I have been a lifelong panty-boy. I had been buying my own stuff since then but felt a bit uncomfortable. My wife, Linda didn’t mind buying me silky things but didn’t always hit the mark thinking what I might like. When the internet came along I started buying my silky things on-line.
By now just talking about wearing panties and the feeling of silky nylon was causing my cock to rise in my panties, and Elaine’s face was beginning to flush and her breathing speed up. She reached out and touched the head of it through my panties and I shuddered with a small dry orgasm. I learned to have them over the years while edging toward the big explosive cums that one enjoys after edging for hours and perhaps days at a time. If you haven’t learned to experience them, you should get busy and learn because they are very nice, and when you do finally have that big cum it will leave you exhausted and breathless. They are especially nice when enjoying them with someone you love.
“Should we take care of that now or would you like to wait until later?” she asked. “As you like,” I replied.
She led me to her bedroom and had me lie on the bed. Then she started stroking my cock through my panties; not quite jacking me off, but running the backs of her fingers up and down through my panties. My cock was straining to get out of my panties and my balls were drawing up like they were ready to blast my cum out. Then she moved around, placing her crotch over my face. Her pussy looked delicious in her panties and I so wanted to get my nose and tongue into it. But as I raised my head, she raised herself up just out of my reach, but kept rubbing my cock through my panties. I moaned and grunted and tensed as my orgasm had arrived and there was no stopping it. Then she lowered her pussy to my face and allowed me to lick and suck her to her own cum.
My panties were soaked with my own cum.
We showered together, and with the hand-held shower wand set to a hard vibration against her distended clit, we brought her to several more orgasms. After her last cum, I went down on my knees and licked and sucked her again until at last she pushed me away saying “Too much, it’s beginning to feel painful. We washed each other vigorously, she spending an excess of time washing my cock and my balls. At last, she washed my ass, sliding her finger into my anus. She pushed as far as the finger would go and touched my prostate through the lining of my rectum. That elicited a response from my cock and made me grunt with appreciation.
“Oh, you like that, do you?” she asked. I shuddered through a small orgasm that I had learned how to do from a girlfriend some years back. And said, “YES.”
“Do you use toys back there?”
I replied that I had used small vibrators and an anal prostate stimulator, as well as the anal douche. I like to keep myself clean for occasions like this. They don’t happen all that often, but I try to be prepared.
We left the shower and toweled each other dry. We returned to the bedroom where she pointed to a large bureau in the corner. “Darryl’s things are in the bottom two drawers and mine are in the upper four drawers. Help yourself to whatever interests you. I’ll go make us some drinks, she said and left the room. Since I really knew what I wanted were here things. I decided to wait on that and explore what might Darryl be interested in when he wasn’t being the Alpha Male. I opened the bottom drawer and found an arsenal (pun intended) of toys, including masturbators, butt plugs, vibrators, and nipple clamps. Ooh, Darryl, you naughty boy, I thought. The next drawer up contained an array of slutty lingerie, including panties, teddies, suspenders and very whorish hose.
Then I went through Elaine’s things and found some more conservative lingerie, including my favorite Vanity Fair full brief panties, stay-up stockings, a light bra and negligee to match. I was surprised that it all fit me fairly well, as if Elaine had been shopping just for me.
She was waiting with drinks for me in the lounge. While I had been nosing through their drawers, she had managed to dress herself in very sexy, but moderate loungewear. “very nice and just what I’d have chosen for you. You turn out very nice as a panty-boy.”
“Since I know it will be some time before you are able to perform again, I have something I need to discuss with you. You see, Darryl is somewhat prudish outside the bedroom, but when we retire at night he turns into an all-out sissy. I want to draw him out to where he is comfortable around others in his closet persona. I know that he is bisexual because of the things he asks me to do to him when we are playing our bedroom games. I think he would like to either fuck or be fucked by another man, and with another woman playing along with them. Do you think you could help me with that, Frank?”
“If it means I will get to finish what you and I have started, I’d be more than happy to help!” I said, a bit too eagerly.
We had finished our drinks. Then Elaine said, “Lets go to bed and finish what we were doing, then.” Ever happy to oblige, I followed her back to the bedroom. She took the lead and gave me a very sexy hug and deep kiss while rubbing her ample breasts against mine and her pussy bump against my cock in my panties. It immediately rose to the occasion and nuzzled its way between her thighs. The silkiness of layers and layers of silky nylon was having its effect on me and my knees grew weak. I knew I was not going to last long this time either, so backed away. Elaine was panting and reached out to stroke my nipples with the back of her hand the way she had earlier done to my cock that made me squirt my cum all over myself. I felt myself having another orgasm, this time in my own man-tits. It radiated down to my groin and up to my brain as I shuddered groaned. ‘I didn’t know you were multi-orgasmic, or that your breasts were so sensitive. I’m going to have fun with you,” she cooed.
I sat down in a chair by the bed to let myself settle down. My cock was very hard and leaking precum. Elaine turned her back to me and lowered herself into my lap, raising her gown and lowering her panties as she moved. I reached down to uncover my cock as she moved into position and her pussy slid down on my cock. Fully impaled, she leaned back against me and began a slow rocking motion. I reached around and fondled her tits with one hand while diddling her clit with the other. We both came in very short order with her gyrating her hips and my cock spewing great ropes of semen into her.
Here I was, fucking my best friend’s wife in his bedroom and wearing his wife’s lingerie. I wondered what he would think if he knew that I am a hard-core panty boy. Would he think I am gay? A pervert, perhaps? As if she could read my mind, Elaine said “Darryl talks in his sleep, you know? I heard him the other night talking about things in his ass while having his cock sucked. And he mentioned your name just before he had a spontaneous ejaculation. ‘Oh, God, Frank, I’m cumming! Suck harder and squeeze my balls! Fuck me harder! And then he groaned and shot his cum all over my ass. My vibrator was humming away in my pussy and I had a really good cum. Almost as good as you just gave me.”
Just then the phone rang and Elaine answered it. I figured it was a good time to relieve myself, so I went to the bathroom to pee. I ***** her panties that I had cum in earlier and gave them a sniff and a lick. I felt the stirrings in my cock, but they were not sufficient to raise it from the dead. I was finished for the night. I decided to take a quick shower, and the warm jet beating down on my back and shoulders relaxed me and told me it was time for bed. I toweled off and padded to the bedroom Darryl and Elaine shared and helped myself to another serving of panties, nightie and a light bra. I finished the bourbon and water and took the glass to the kitchen. Elaine was just finishing up her phone conversation. She rang off and told me it was Darryl who had called and said he would be home on Saturday and would we all like to get together for a cook out. I suggested we meet at my house since I have a pool, nice deck and some clothes that might fit Darryl. It was agreed and I left.
Promptly at six pm on Saturday afternoon, Darryl and Elaine arrived at my house. We went through the house to the pool and sat under the umbrella. I invited them for a swim, but they hadn’t brought their swimsuits. Elaine had told me that Darryl is sensitive about the size of his cock, so I figured he would not want to swim in the nude. Elain could swim in her panties and bra and I could loan Darryl a swimsuit. Or we could all swim in our underwear since the fence and hedge are over eight feet tall and the nearest neighbor is hundreds of feet down the road. I shucked my trousers and stood before them in a black nylon brief, and nothing else. Elaine stripped to her bra and panties which were a matched set of petal pink bikini style. Darryl shyly pulled off his shirt, shoes and trousers and stood in boxer shorts and his socks.
My cock was responding to Elaine’s near nakedness, and Darryl looked hungry. I said nothing but dove into the cool water and swam across the pool. Elaine came in and joined me leaving Darryl standing in his boxers. He pulled off his socks and jumped in and swam over to where Elaine and I were playfully splashing water on each other. Elaine turned to Darryl and gave him a wet hug and a sensuous kiss. I swam up to the deep end of the pool and treaded water for a few minutes, getting a bit of exercise. Then Darryl followed and treaded water with me. Then he said “Your underwear looks like women’s.”
“It is,” I replied. “Would you like to try it? They are so comfortable, and the nylon feels good sliding around my cock and balls.”
“I don’t know,” he answered. “Elaine might think I was turning gay or something.”
Then I told him about Elaine’s catching me jacking off with her panties, that I knew he loved to suck my cum from them while sniffing them. I left out the part about me fucking her as I didn’t know how he would react.
“Busted, then, am I?”
“Yup,” I replied. We’re both busted, so it’s all out in the open and we might as well enjoy it.”
Elaine swam up to us and asked what we’d been discussing so quietly.
I said “I was just telling Darryl about you catching me masturbating in and with your panties, and that you and I both know that he likes the taste of my semen directly from them.”
“Well,” she said. Then she hugged Darryl and gave him a deep sensual kiss. She backed up to me so that her shapely butt pressed against me, rubbing against my panty covered cock. I was responding. “Let’s get out and have a shower. Then we can get down to some serious business.”
After quick showeres we repaired to the kitchen and prepared a quick snack and a glass of wine. We sat wrapped in towels that kept us warm against the cool breeze blowing through the open windows.
Elaine asked me “Why don’t you go and get your things and give us a fashion show?” When I rose to go, she moved to the sofa with Darryl and started getting amourous with him. By the time I left the room she had his towel removed and was stroking his cock and swallowing his tongue.
I went to my bedroom and dug around for some lingerie. I came up with a lace covered full brief panty and bra set and a dressing gown to match. They were all pale yellow with pretty bows in strategic places, over my nipples and the head of my cock. My baby-smooth skin was excited by the soft, silky feel of the nylon fabric. All my sensitive places, from my earlobes to the backs of my knees were electrified.
I returned to the living room and found Elaine on her knees with Darryls cock in her mouth and one hand kneading his balls. One hand was at his breast rubbing and squeezing his nipples. Darryl’s breathing was becoming fast and ragged, and he was very flushed. In one motion Elaine moved her hand from his balls to deep between his thighs. I saw and heard Darryl grunt and thrust his hips forward. Then he groaned, and I could see Elaine’s cheeks swell as she took his seed into her mouth. Then she swallowed. Darryl then relaxed as he came down from what appeared to be a very strong orgasm.
“I think he liked what I did to him,” Elaine said, looking at me. She reached out and touched my cock through my silky panties and asked, “Would you like some of that?”
“Yes. OOOHH yes!”
She took Darryl’s hand and placed it on my panties, right over my quivering cock. He closed his hand around my cock through the silky nylon fabric and shuddered as if he were having a small orgasm like a woman would, having her clitoris touched. I have to admit that I, too, experienced a small cum when he touched me. Elaine rose and came around behind me, rubbing her breasts against my back. “You don’t need this,” she said as she unclasped my bras. She reached around under my arms and tweaked my nipples through the satin fabric of the bra cup and I gave another little shudder.
“You see, Darryl, Frank likes to have his titties played with. And I see you like playing with his cock through his panties. And Frank likes it too. Wouldn’t you like to feel what it’s like to have silky panties rubbing against your cock, balls and ass?”
“I…I don’t know” said Darryl, “Do you like it Frank?”
“Oh, yes, Darryl. I like it a lot. I was wearing these panties when I first jacked off in them. They are actually Elaines. They felt so good in my hand and on my cock the first time that I just had to try them on. And when I did, I stroked it and came almost immediately.”
“I caught him last week using my panties and sniffing them. When I caught him he was wearing my panties and sniffing another pair. Remember when I caught you licking and sniffing my panties? You were actually licking Frank’s cum from these panties he’s wearing right now.”
Darryl’s face grew red at being found out by me that he had been licking my cum from Elaine’s panties. But he continued stroking my cock and I could see that his own cock had recovered from his orgasm and had begun to rise. Elaine told him “Now that we all know what you two do with my panties, why don’t you give Frank’s cock a little suck while you jack him off? Go ahead, Darryl. Make Frank cum in my panties. It’s better from the source than after it’s all dried and stale. Take it in your mouth. Feel the silky nylon encasing his cock. Jack him off and take his cum in your mouth.” His hand continued to stroke me and my cock grew harder. Elaine rubbed her tits over my back with more pressure and as she pulled and tweaked my nipples I edged closer to Darryl’s face. He leaned forward a bit, then kissed the head of my cock. He groaned and took the head into his mouth. He sucked on my knob while continuing to jack me off. All of a sudden he took the whole thing in down to my balls and the warmth and pressure were too much for me. I felt my cock swell, and then Elaine shoved her finger into my anus. The sensation of her finger in my ass and Darryl’s sucking my cock was more than I could handle and I collapsed, semen spewing from my cock as it slipped from his mouth. Elaine was able to hold me up and keep me from falling, but I was weak. Darryl continued to stroke my wilting cock until I was totally spent. Then he took me back into his mouth and sucked all my cum off of me.
We three collapsed into chairs, breathing hard but satiated. After about ten minutes, Elaine stated that she was hungry and would call for pizza since it was getting too late for a regular supper. I needed a shower, and so did Darryl, so we did that while Elaine ordered the pizza.
While in the shower Darryl told me that he really admired my totally shaved body and asked if I could help him achieve the same result as a surprise for Elaine. I turned up the hot water and lathered up a cloth with a scented body wash. Then I started at his face and washed him thoroughly from head to toe. I paid very special attention to his ass crack, his balls and his cock. By the time I finished washing his cock he was hard as stone and breathing just as hard. “Finish me off, Frank. I need to cum.”
“I think you can wait a bit longer. Let’s get you really clean and fresh. Then you can show Elaine what a stud you can be.” Then I lathered up the cloth again and soaped him up good and proper. After I had hiim covered with foam, I took the razor and shaved him completely, right down to his toes. Except for his head, he was totally hairless, like a Nubian princess. After I rinsed him off, I removed all of my own body hair, paying special attention to my anus and perineum. Soon I was as smooth as Darryl. We finished the shower with both our cocks standing strait from our bodies. “Let’s get dressed” I sd.
I guided Darryl to the bedroom and had him stand in front of the full-length mirror on the closet door. Then I fished around in my dresser and came out with a panty, bra, negligee and a garter belt. Next, I found a set of silk stockings. I had Darryl stand still while I put the bra and garter on him. Th ass.e fabic was very soft and silky and were a bit small for him, but his man-tits stood proudly and his ass cheeks poofed out nicely. He put the negligee on himself and let it d**** open.
The it was my turn to dress. I started with a pair of pink stockings. Then I placed the matching garter on my hips, straightened it and attached the garters. Then a pink push-up bra. Next came a full panty, also in delicate pink. I pulled the panties up over my legs and past my balls and over my cock. The silky nylon felt so good on my ass, and by the time I put on m y dressing robe my cock was leaking precum.
Darryl wanted a wig that made him look like a slut, but I liked myself the way I am When we went out to the living room, Elaine was waiting with plates and a very large combination pizza. She also had two bottles of re wine, an opener and three very tall glasses. I poured the wine and Elaine served the pizza. She said that she had ordered extra anchovies because she knew that Darryl and I were going to need the protein. “You two look good enough to eat, but we’d better have this pizza first or we may starve,” she said. Then she went to fetch a gown to wear with supper. I told Darryl to eat up, and we both chowed down, washing it down with wine. Elaine came out after a shower wearing some sexy lingerie that complimented ours.
She said “I want you both to make me cum tonight, and then I’ll make you both cum. But I get to choose how.” She then reached for Darryl’s cock and stroked it through his silky briefs. It started to grow and pulse with his heartbeat. “Kiss him, Frank.”
I leaned in and moved my mouth to his, and then to Elaine’s, dipping my tongue between her lips. She touched my breasts with her other hand and tweaked my nipples eliciting a groan of pleasure from me. My own cock was already straining in my panties as she dropped her hand, now holding two similar, but different cocks. Darryl’s is long and thin and my cock is short but very thick. Keeping her grip on both our cocks, Elaine led us to the bedroom. There she lay on the king-sized bed and said in her sultriest voice “Come here and make me cum.”
My panties were already soaked with pre-cum as Elaine rubbed and stroked both our cocks and then she rubbed them together his cock poking my balls and mine poking his pubic bone. The double layer of nylon felt exquisite against my cock and balls. I knew then that my sexual relationship with Darryl was about to climb to the next level. Elaine motioned me to lie on my back and she positioned herself so that her pussy hovered over my face. Darryl immediately knelt and began sucking my cock and fondling my aching balls. Elaine’s pussy was dripping with her juices and my saliva as I tongued and sucked at her hole. I reached back and pushed her forward so that I could get at that perfectly round and soft ass, and wiggled my tongue as if knocking at her puckered back door. The taste and aroma of her tight butt was devine and I spent several moments tongue-fucking her ass. Darryl’s mouth and tongue were working their magic on my cock, and I could feel my orgasm building. He squeezed my balls and pulled them out from my body just as my prostate spasmed, and I shot thick ropes of heavy cream down his throat. When I was spent, he kept pumping my cock and pulling on my balls.
I was yelling into Elaine’s ass and the vibrations from my throat and tongue trigger an anal orgasm in her. I felt a spasm deep within her at the top of her pussy, and of a sudden a hot splash of something very wet hit my throat and ran down both sides of my neck. I pulled myself forward in order to get what was left of her golden nectar. Her urine was hot and salty as it splashed against my tongue, and together with Darryl sucking my cock triggered a terrific dry orgasm in me.
“I’m sorry,” she said, as she moved away from me and ran to the bathroom. Apparently Darryl had missed the water-sport portion of the program as he just kept nursing on my already soft penis. I could hear the water running in the shower, so I knew that Elaine would be a few minutes. I asked Darryl if he would stop and let me rest for a while, but he said he had still not come and wouldn’t mind if I would ‘do” him.
“I’m just too exhausted right now, but if you let me rest a bit I promise you a nice treat.”
“Ok,” he said, but I could tell that he was disappointed. I rolled over on my side and went to sleep. I must have been out for a while, for when I woke I felt like I was enveloped in a warm cocoon. I realize that I was caught in a “sandwich” between Darryl and Elaine with Elaine spooned into my embrace and Darryl at my back. Both were snoring softly, but pushing into me. Darryl’s cock was nudging my ass wile mine was doing the same to Elaine’s vagina. Only the tips of our cocks were being entertained and just barely making an entry into their targets. Elaine’s ample nether cheeks were holding me back from making full penetration, and just no lubricating fluids at my anus, so Darryl couldn’t push into me. I didn’t want to disturb either of them and I was enjoying the full contact of two warm bodies wrapped so tightly around me. I just relaxed and enjoyed the sensation.
I could feel Elaine getting wetter and her natural lubrication started to spread over my cock allowing me further access to her vagina and thus lubricating her anal sphincter. She was emitting copious amounts of lubrication as she began a serious fucking motion. I reached around her and started massaging her clitoris. Her breathing became ragged and heavy as she neared her orgasm, and when she reached it, expelled a tremendous gush of fluids, I scooped up as much of it as I could, and reached behind me and started rubbing it over my cock and Darryl’s cock. Soon, the head of his cock popped into my rectum, as I relaxed and let him penetrate me.
We were both surprised, as He had never fucked another guy, and it was the first time anything other than my own fingers, and the occasional small probe had been in my own ass. It was a bit uncomfortable at first, but the discomfort very quickly changed to pleasure and I started alternately pushing forward into Elaine’s pussy and back against Darryl. We all three soon set up a rhythm, and the pleasure of fucking and being fucked started building. Soon I was out of control and was slamming back and forth against my two lovers. All at once, we all tensed against each other. My balls felt like they were being torn from me. Elaine’s vagina clamped like a vise around my cock, my anus spasmed, and Darryl screamed in pleasure/pain as his semen was torn from him and sprayed against the walls of my rectum. He was embedded so deep in me that the head of his cock massaged my prostate, triggering my own cum. I groaned and shot great ropes of semen into Elaine. Each round of spasms from the three of us triggered another, and it seemed we came and came for several minutes.
Finally, we separated and lay exhausted on the bed. Our breathing and heart rates began to return to normal. Within minutes we were all dead asleep, and in my head visions danced of naked boys and girls, arms, legs and other appendages intertwined and writhing together in orgasmic bliss.