Threesome with Married Couple
This adventure occurred around 2010. My college class has reunions every five years, which occur in the late spring in the week after commencement, and I try to make every one of them to catch-up on the stories and reminiscences with my classmates. Ohio is full of small towns with small, liberal arts colleges where everyone lives on campus 24/7, and people get to know their dorm-mates and members of their fraternity or sorority as well as they know their own blood kin, and my alma mater is one of those schools. In other words, the reunion weekend is a big fucking deal, and the college schedules group activities almost continuously from the cocktail hour on Thursday until noon on Sunday.
As my earlier posts have specified, I am a late bloomer as a transgender person, and really didn't discover the nature of my personality until I was in my late 30's and early 40's. So, although I'd been curious, and had even experimented a bit with crossdressing and bisexuality when the prior two reunions had taken place I had not really accepted myself at those times. However, by the time this particular reunion was scheduled, I had embraced both my gender dysphoria and my newfound love for cock. Since I was going to be on the road traveling, with my dog in a kennel, and no possibility of interruption by c***dren, friends, ex-wives, or neighbors, I had been busy trying to arrange a hookup for sometime on Sunday afternoon or evening at a place somewhere close to the route which would take me home.
I was fortunate enough to make contact with a couple who lived in another small town about fifty miles from my college, and had made arrangements with them to stop at their house in the mid-afternoon of my return trip. So, when I set out on Thursday afternoon I was in a positive mood for both the anticipated happy times with my classmates at the reunion, and for the adventure of my first threesome with a male-female couple.
I woke up early on Sunday morning, and, despite having consumed a rather unfortunate amount of alcohol during the preceding evening, was able to make it to a buffet breakfast where I had a last farewell with my friends. Afterwards, I went back to my motel room, and did a prep, shower, and touch-up shave, and then put on my make-up and girl clothes. I called the couple on my cell phone, confirmed that they were still agreeable, and got on the road. The drive took only about an hour, and I arrived at the home of the couple sometime in the early-mid afternoon.
Their home was in a small development which probably dated back to the 1950's, and was a red brick and white clapboard colonial with nice shrubs and plantings, and a green lawn which would've made Scott's proud. It's been a while, but if I recall correctly I was wearing summer casual clothes, shorts, Keds, a sleeveless blouse, sunglasses, a shoulder length auburn wig, and some sort of shoulder bag full of touch-up cosmetics, hairbrushes, et cetera.
The man answered the door, and invited me in. He was cordial and polite, but a bit flustered, which wasn't surprising. He and I had been exchanging messages for about ten days, and I was aware that this was to be their initial foray into swinging.
He appeared to be a few years younger than I am, somewhere in his mid/late forties, stood a bit taller than me, about six-one or so, and looked like he worked-out moderately. He was probably forty or fifty pounds heavier than me, and gave an impression of masculine strength. He was wearing pair of chinos and a a polo shirt, and spoke very well, and actually was more attractive in person than in his photos. Since this was another small college town, I wondered if he might be associated with the local college.
The woman was nowhere in sight when I first arrived, but she came downstairs a few minutes later, and introduced herself. She was about the same age as the man, and tallish and well-built. Like him, she looked better up-close and personal than in snapshot type photos which I had seen.
God bless me, but after ten years I cannot now remember their names at this point in time. Alas! The names were pretty much generic WASP, so for the purposes of the story I'm going to call them Jim and Debbie.
Drinks were produced, Gin and Tonics if I recall aright, and the three of us sat in the living room and chatted about things that really weren't germane to the underlying proposition that hopefully we were soon going to all be naked and exchanging bodily fluids. At some point as an icebreaker Debbie asked me if I had been crossdressing for a long time, and I explained as briefly as possible that I had been CD'ing for about fifteen years, and engaging in sex while presenting as a woman for all but a couple of those years. I had explained all this to Jim, her husband, but since almost all trans gurls love to talk about themselves I wasn't put-off by reiteration. Debbie was fairly confident, and explained to me that she was curious, but unsure about how far she wanted to go, and that she wanted to be a good partner and help Jim satisfy his curiosity about transgender sex. Since he had already fully explained to me that it was entirely likely that his wife might only want to observe, and not participate, I wasn't surprised, and I remember explaining to her that although I was technically bisexual, my preference was to be the "female" partner only, and that while I would be able to penetrate her if she desired, I would be happy with whatever level of participation which made her feel comfortable.
She surprised me, with a chuckle, and clapped her hands, and said, "Well, in that case, let the fucking begin!" I slid across the sofa on which Jim and I were seated, and French kissed him deeply, and asked Debbie if she was comfortable with that. Receiving an affirmative reply, I kissed him again, and ran my hands across his chest. His pects were nice and firm, and I found that to be exciting. We made out for several minutes, and the woman watched with interest, but was silent. I helped Jim pull his shirt over his head, and that exposed a chest which I recall as being moderately hairy, and I sucked on his nipples, which made him moan. He was running his hands over my bare legs, and squeezing my ass through my shorts, so I stood-up and took-off my shorts and blouse, leaving the pink thong bikini panties, pink sports bra, and latex breast forms in place. I remember being pushed back on the couch, and feeling his fingers probing me, and squeezing my clitty. Then, he slid down, and took me into his mouth. I heard the woman react to that with a gasp. He was talented, and I leaned back and let him suck on me while he fingered my pussy. After a few moments, he stood, and thrust his erect cock towards my face, and I submissively took him into my mouth in one greedy, swallow. Jim's cock was not especially memorable, neither amazing large nor disappointingly small, just a nice six inches, plus or minus, and pleasingly firm, and I didn't gag as much as I sometimes do when I deep throat.
I told him to sit down, and when he did that I slid to me knees between his legs, and began to enjoy his cock. Debbie changed her position to get the best viewing angle, and was watching from a fairly close point, maybe 2-3 feet away from my face. She had disrobed herself while this action was occurring, and was masturbating while she watched. After I had sucked her husband's cock for several minutes, she said, "I want to see you fuck her, baby! Don't cum in her mouth!"
I pulled my mouth away from its posture of sissy submission to the power of cock, and said that sounded wonderful, and that I would love to be fucked my his beautiful cock. He took me by the hand, and I stood, stepping out of my now stretched panties, and he led me to a large overstuffed chair and positioned me facing the back of the chair, kneeling on the cushion, with my pussy fully exposed. I felt him put more lube inside me with his fingers, and then felt him position his cock at my anus. As an aside, this is one of my favorite sexual moments, there is something absolutely slutty and submissive about offering my body to a man, and then staying in suspense and anticipation while he decides how he wants to penetrate me, fast, slow, hard, gentle, deep, shallow. He slid into me smoothly, and to a good, satisfying depth, and I'm pretty sure that I moaned, and so did Debbie.
Jim fucked me for several minutes on the chair, and then he got me on my elbows and knees on the carpet. Debbie was naked, and frigging herself all the time, and encouraging him while he humped on me vigorously. Then she stood in front of me, and asked me, "Do you want to eat my pussy, sissy? Do you want to eat my pussy, will you be my bitch?" And, at that moment in time there was nothing in the world so important to me as being able to sample her juices with my lips and tongue. She had a trimmed bush, and firm body, and was a feminine goddess to me in my fevered, cock-drunk state. I moved involuntarily towards her, and Jim's cock fell out of my pussy in mid-stroke, and he slapped my ass hard, and told me to stay still and take his cock like a sissy whore should. He continued to fuck me while Debbie teased me, and I began to drizzle a thin but steady stream of seminal fluid. Then he said that if anyone was going to eat his wife's pussy while he was fucking me it would be him, He rolled me over on my back, shoved a pillow under my lumbar, grabbed my ankles, spread me wide, and began to fuck me more. Debbie stepped up until her ass and pussy were directly over my face, and I had a perfect view of Jim as he licked and nibbled at her pussy while he pounded me.
It was all a bit too much sensory load for him, and he didn't last long until I saw his eyes roll back in his head, and then he came in warm spurts inside my pussy. Almost immediately after his last spasm, he rolled off me, and lay on the floor panting. Debbie was pretty much fully involved by now, and she squatted down over my face, burying my mouth and nose in her pussy, and she began to grind on me, exhorting me with more "eat my pussy Sissy" commands. I was obviously more than willing to obey implicitly, and eagerly searched for her clitoris with my tongue. When I found it, she squealed, and continued her verbal commands, which drove me into a frenzy. My shoulders were partially pinned down by her body placement over my chest and head, but I was able to work my arms free, free, and while I held her pussy close to my mouth, I managed to insert a slippery finger about two knuckles into her ass, and that caused her to climax, bucking and moaning in a short time.
Jim had watched all this, of course, and he simply said "Wow!" as he watched his wife roll off my body onto the floor. He asked me if I wanted him to get me off, but I replied, somewhat pridefully and somewhat embarrassed by my sissiness, that I had already cum while he was fucking me. He laughed, and said, "In that case the Gin, limes and tonic water are on the kitchen counter, go mix another round of drinks like a good sissy maid should!" I smiled, and hastened to comply.
We talked about hooking-up again, but sadly there is more than a hundred mile drive involved from my home to theirs, and it never seemed to work out. I lost contact with them a few years later. Too bad, because they are a very hot couple, indeed.
As my earlier posts have specified, I am a late bloomer as a transgender person, and really didn't discover the nature of my personality until I was in my late 30's and early 40's. So, although I'd been curious, and had even experimented a bit with crossdressing and bisexuality when the prior two reunions had taken place I had not really accepted myself at those times. However, by the time this particular reunion was scheduled, I had embraced both my gender dysphoria and my newfound love for cock. Since I was going to be on the road traveling, with my dog in a kennel, and no possibility of interruption by c***dren, friends, ex-wives, or neighbors, I had been busy trying to arrange a hookup for sometime on Sunday afternoon or evening at a place somewhere close to the route which would take me home.
I was fortunate enough to make contact with a couple who lived in another small town about fifty miles from my college, and had made arrangements with them to stop at their house in the mid-afternoon of my return trip. So, when I set out on Thursday afternoon I was in a positive mood for both the anticipated happy times with my classmates at the reunion, and for the adventure of my first threesome with a male-female couple.
I woke up early on Sunday morning, and, despite having consumed a rather unfortunate amount of alcohol during the preceding evening, was able to make it to a buffet breakfast where I had a last farewell with my friends. Afterwards, I went back to my motel room, and did a prep, shower, and touch-up shave, and then put on my make-up and girl clothes. I called the couple on my cell phone, confirmed that they were still agreeable, and got on the road. The drive took only about an hour, and I arrived at the home of the couple sometime in the early-mid afternoon.
Their home was in a small development which probably dated back to the 1950's, and was a red brick and white clapboard colonial with nice shrubs and plantings, and a green lawn which would've made Scott's proud. It's been a while, but if I recall correctly I was wearing summer casual clothes, shorts, Keds, a sleeveless blouse, sunglasses, a shoulder length auburn wig, and some sort of shoulder bag full of touch-up cosmetics, hairbrushes, et cetera.
The man answered the door, and invited me in. He was cordial and polite, but a bit flustered, which wasn't surprising. He and I had been exchanging messages for about ten days, and I was aware that this was to be their initial foray into swinging.
He appeared to be a few years younger than I am, somewhere in his mid/late forties, stood a bit taller than me, about six-one or so, and looked like he worked-out moderately. He was probably forty or fifty pounds heavier than me, and gave an impression of masculine strength. He was wearing pair of chinos and a a polo shirt, and spoke very well, and actually was more attractive in person than in his photos. Since this was another small college town, I wondered if he might be associated with the local college.
The woman was nowhere in sight when I first arrived, but she came downstairs a few minutes later, and introduced herself. She was about the same age as the man, and tallish and well-built. Like him, she looked better up-close and personal than in snapshot type photos which I had seen.
God bless me, but after ten years I cannot now remember their names at this point in time. Alas! The names were pretty much generic WASP, so for the purposes of the story I'm going to call them Jim and Debbie.
Drinks were produced, Gin and Tonics if I recall aright, and the three of us sat in the living room and chatted about things that really weren't germane to the underlying proposition that hopefully we were soon going to all be naked and exchanging bodily fluids. At some point as an icebreaker Debbie asked me if I had been crossdressing for a long time, and I explained as briefly as possible that I had been CD'ing for about fifteen years, and engaging in sex while presenting as a woman for all but a couple of those years. I had explained all this to Jim, her husband, but since almost all trans gurls love to talk about themselves I wasn't put-off by reiteration. Debbie was fairly confident, and explained to me that she was curious, but unsure about how far she wanted to go, and that she wanted to be a good partner and help Jim satisfy his curiosity about transgender sex. Since he had already fully explained to me that it was entirely likely that his wife might only want to observe, and not participate, I wasn't surprised, and I remember explaining to her that although I was technically bisexual, my preference was to be the "female" partner only, and that while I would be able to penetrate her if she desired, I would be happy with whatever level of participation which made her feel comfortable.
She surprised me, with a chuckle, and clapped her hands, and said, "Well, in that case, let the fucking begin!" I slid across the sofa on which Jim and I were seated, and French kissed him deeply, and asked Debbie if she was comfortable with that. Receiving an affirmative reply, I kissed him again, and ran my hands across his chest. His pects were nice and firm, and I found that to be exciting. We made out for several minutes, and the woman watched with interest, but was silent. I helped Jim pull his shirt over his head, and that exposed a chest which I recall as being moderately hairy, and I sucked on his nipples, which made him moan. He was running his hands over my bare legs, and squeezing my ass through my shorts, so I stood-up and took-off my shorts and blouse, leaving the pink thong bikini panties, pink sports bra, and latex breast forms in place. I remember being pushed back on the couch, and feeling his fingers probing me, and squeezing my clitty. Then, he slid down, and took me into his mouth. I heard the woman react to that with a gasp. He was talented, and I leaned back and let him suck on me while he fingered my pussy. After a few moments, he stood, and thrust his erect cock towards my face, and I submissively took him into my mouth in one greedy, swallow. Jim's cock was not especially memorable, neither amazing large nor disappointingly small, just a nice six inches, plus or minus, and pleasingly firm, and I didn't gag as much as I sometimes do when I deep throat.
I told him to sit down, and when he did that I slid to me knees between his legs, and began to enjoy his cock. Debbie changed her position to get the best viewing angle, and was watching from a fairly close point, maybe 2-3 feet away from my face. She had disrobed herself while this action was occurring, and was masturbating while she watched. After I had sucked her husband's cock for several minutes, she said, "I want to see you fuck her, baby! Don't cum in her mouth!"
I pulled my mouth away from its posture of sissy submission to the power of cock, and said that sounded wonderful, and that I would love to be fucked my his beautiful cock. He took me by the hand, and I stood, stepping out of my now stretched panties, and he led me to a large overstuffed chair and positioned me facing the back of the chair, kneeling on the cushion, with my pussy fully exposed. I felt him put more lube inside me with his fingers, and then felt him position his cock at my anus. As an aside, this is one of my favorite sexual moments, there is something absolutely slutty and submissive about offering my body to a man, and then staying in suspense and anticipation while he decides how he wants to penetrate me, fast, slow, hard, gentle, deep, shallow. He slid into me smoothly, and to a good, satisfying depth, and I'm pretty sure that I moaned, and so did Debbie.
Jim fucked me for several minutes on the chair, and then he got me on my elbows and knees on the carpet. Debbie was naked, and frigging herself all the time, and encouraging him while he humped on me vigorously. Then she stood in front of me, and asked me, "Do you want to eat my pussy, sissy? Do you want to eat my pussy, will you be my bitch?" And, at that moment in time there was nothing in the world so important to me as being able to sample her juices with my lips and tongue. She had a trimmed bush, and firm body, and was a feminine goddess to me in my fevered, cock-drunk state. I moved involuntarily towards her, and Jim's cock fell out of my pussy in mid-stroke, and he slapped my ass hard, and told me to stay still and take his cock like a sissy whore should. He continued to fuck me while Debbie teased me, and I began to drizzle a thin but steady stream of seminal fluid. Then he said that if anyone was going to eat his wife's pussy while he was fucking me it would be him, He rolled me over on my back, shoved a pillow under my lumbar, grabbed my ankles, spread me wide, and began to fuck me more. Debbie stepped up until her ass and pussy were directly over my face, and I had a perfect view of Jim as he licked and nibbled at her pussy while he pounded me.
It was all a bit too much sensory load for him, and he didn't last long until I saw his eyes roll back in his head, and then he came in warm spurts inside my pussy. Almost immediately after his last spasm, he rolled off me, and lay on the floor panting. Debbie was pretty much fully involved by now, and she squatted down over my face, burying my mouth and nose in her pussy, and she began to grind on me, exhorting me with more "eat my pussy Sissy" commands. I was obviously more than willing to obey implicitly, and eagerly searched for her clitoris with my tongue. When I found it, she squealed, and continued her verbal commands, which drove me into a frenzy. My shoulders were partially pinned down by her body placement over my chest and head, but I was able to work my arms free, free, and while I held her pussy close to my mouth, I managed to insert a slippery finger about two knuckles into her ass, and that caused her to climax, bucking and moaning in a short time.
Jim had watched all this, of course, and he simply said "Wow!" as he watched his wife roll off my body onto the floor. He asked me if I wanted him to get me off, but I replied, somewhat pridefully and somewhat embarrassed by my sissiness, that I had already cum while he was fucking me. He laughed, and said, "In that case the Gin, limes and tonic water are on the kitchen counter, go mix another round of drinks like a good sissy maid should!" I smiled, and hastened to comply.
We talked about hooking-up again, but sadly there is more than a hundred mile drive involved from my home to theirs, and it never seemed to work out. I lost contact with them a few years later. Too bad, because they are a very hot couple, indeed.
3 years ago
