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Exploring with a transsexual

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Anyone here had any experiences in your swinging relationships with a shemale/transsexual?

 

When I was living in SF Bay, I was single at the time and dated a few she-males. I was infatuated with a hot girl that had a cock. I have never tried to add that into my current relationship, but since we have done lots of MFM, I figured I would bring it up to the wife and see how she feels. I have been with 3 TS, and each experience was amazing.

 

Anyone else care to share?

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We have a vanilla friendship with a MTF TS. I can tell you one thing that may help: Do not call them shemales. Most transgendered consider this to be a pejorative term.

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What two4you said.

 

I'm sure location also plays a role. I only met one trans person while I lived in Indiana (22 years, 17ish with memory ;) ). Since moving to Oregon... I couldn't put a number on how many transpeople I've met/talked to. People who don't fit the gender binary often gravitate towards areas that are more welcoming, or big enough that they can blend in. In the Bay area, Portland-ish, and places similar, it's going to be much easier to find people who are openly living their lives as they want to compared to more conservative/traditional areas where people tend to hide that kind of stuff.

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We have a vanilla friendship with a MTF TS. I can tell you one thing that may help: Do not call them shemales. Most transgendered consider this to be a pejorative term.

 

I am very familiar with this. When I lived in SF Bay I learned the hard way haha. However I used that term for the sake of people understanding what I am asking here.

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I think being with a transgender person sounds very interesting and hot. My husband said it is not a turn-on for him at all.

 

I would think it might be easier to find someone on craigslist or okcupid. In our area there is only one mtf person on sls that I know of.

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There is a woman who periodically attends the same club as us. Her height and some angularity in her movement are the only real indicators that she is transgendered. We think she's attractive, but we respond to her as a woman. There's no sense of the transgressive as there would be with a pre-op woman. Too bad, because Mr. Doe has long been fascinated by body alchemy.

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I've played with a woman who was post op MtF. Lots of fun. It was at a party and not everyone knew. She literally still had stitches on her pussy. The main guy I play with fucked her. It was hot.

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Guest eroticart

I had an affair with a MtF transgender a few years before I met my wife. She was probably the most passable TS person I have ever seen, very hot and very well hung. She worked as a beer tub girl in a bar in town and all the guys would hit on her, not knowing she was transgendered. I struck up a conversation with her one night and asked her to breakfast. We ate and talked for hours, during our conversation she mentioned how hot she thought I was and I told her the same. She asked If I was sure that I felt that way, I said I was. She asked, "well, would you feel that way if you found out I wasn't a girl?'

 

I was dumbfounded, she was 5'6" and smoking hot, I had been totally fooled. I told her yes, I would still feel that way. We talked some more and she asked if I would take her home. I did and when we got to her place she invited me in. I accepted, and we had stellar sex. We carried on for 3 days, barely taking a break to eat and sleep. She and I carried on fucking like rabbits for several months, but sadly it was not to last.

 

She had designs on actually having the surgery to become a woman, I told her I wanted her the way she was but understood that she needed to do it for her own sense of well being. She had saved for 6 years to get the surgery and was in the final stages of the counseling to change from a male to a female. She had suffered from gender dysphoria since she was a child. All that was left for her to do was go to her last 3 counseling sessions and book her flight to Thailand for the surgery. I told her before she left that no matter what I wanted to see her after she got home.

 

She got on the plane and I never saw her again. She had timed it so she had let her lease on her apartment run out and didn't renew. I found out later she had returned to her family home in Chicago.

 

I have never been ashamed or self-conscious of my relationship with her because despite her initial deception she was honest and a truly genuine person. I think fondly of her and hope she has had a wonderful life.

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I've developed a fantasy/interest to meet up with a well hung tranny, play with their tits and fuck like animals. I'd love to find one with a 7-8 inch, thick cock, big fake tits and a hot body.

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Maybe when we're in the heat of things and talking DIRRRRTY, they'll let me ;) thanks though for the tip, I forgot about it.

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Well, some of us are not able to run off to the west coast or wherever to indulge our tastes. How might we find such a lady, with or w/o extra equipment for mutual satisfaction?

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Anyone else care to share?
Over the past couple of years I have occasionally played, sometimes even at a swingers' cub, with a transgender person. All of the secondary sexual characteristics are there but, more significant for me, the impressions that this is a woman in a woman's body. And she really, really enjoys sex. Modern surgical technique is remarkably well developed in this area. This woman, very happily, also has a remarkable support group who surrounds her.
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It's still the individual that appeals to me either female or male or mtf on estrogen with small breasts and penis or with implants and a big cock.

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It's still the individual that appeals to me either female or male ...

 

True, personality counts. One always prefers a connection.

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I've had a fetish for transgender for a while now and my wife is attracted to them as well. Neither one of us had ever had sex with a transgender, but we agreed it would be fun to try and we finally, after years of fantasizing, pulled the trigger and called an escort in Central America. The escort was a shapely, plump gal (not at all as advertised on the internet, but still sexy) and was ready to get it on right when she walked in the hotel room. I was a bit shocked when she grabbed the back of my head and started making out with me [brief panic...'oh my God I'm kissing a guy!...to 'hmmm this is actually pretty hot') as my wife got on her back on the bed and sucked both of us off.

 

Plenty of sucking and kissing then she finally fucked me for a little bit, but it was too painful the way she just shoved her dick in (Great learning point for me about how my wife feels during anal sex lol !!). Finally she just jacked off on my stomach then jacked me off. Overall it wasn't at all what I thought it would be like, but we had a great time and I was glad we gave it a try. I'd definitely do it again, but next time with an escort that was more into women so my wife could be more included. So much fun for my wife and I to experience the butterflies together and to have such a unique sexual experience together!

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My first bi experience was with a now very famous Shemale in London on a business trip years ago. Drop dead gorgeous petite, long blonde hair and all woman except the 7.5" cock. Super person too. I "knew" I was bi, but didn't really know for sure. This was a low key way to find out. 3 hours of the absolute best sex I have ever had!! We did everything possible. It worked for me and she really helped me become comfortable with my bi feelings. It turns out sex with Shemales is great, but different than with men. I like both. With men it's just about the physical experience, no attraction otherwise. I have played with and topped a couple of CDs and TVs over the years, but these days I'm 100% submissive with men.

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On 4/29/2020 at 6:45 PM, Yourfunfriends said:

This is one of our fantasies. Boobs AND cock? Absolutely!

My wife and I have talked about transsexuals, and it doesn't appeal to either of us.  Interestingly, however, Daniela is bisexual (likes boobs and cock (just not on the same person) AND pussy) and I have an attraction to butch women.  Not extremely so, but athletic, small breasted, short hair women, no makeup.  It's not my real preference, but I'm also turned off by women who have fake boobs, too much makeup, etc. - the TV newswoman type.

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Nope…not for us!  Here's your sign….."if it's got a dick it's NOT a chick".

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What about a hermaphrodite anyone had an experience I'll be open but the wife not a player?

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We have happened to play with two different male to female transgenders pre-op, who happened to be at parties we attended. They were fun, sexy people, who had different equipment. Very much enjoyed it.

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It's NOT an opinion, its a biological fact!  Female humans do not have dicks, male humans do! You want to dress like a girl or lie to people and tell people you are a girl? That a choice and maybe a bad one depending on the circumstances.  You can "identify" all you want but saying you're something rather than being that something are two entirely different things. I self identify as a billionaire but the local Bentley dealership will not sell me a new convertible based on that self-delusion even though I WANT one really badly!!!!. 

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I think a lot of guys are not interested in other guys, so it makes sense that they are not interested in guy with breasts.

 

The human brain is the sex organ, and like taste in food, it decides what is and is not sexy.

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We would absolutely entertain the thought of a trans person. But first and foremost, are they a nice and good (and clean!) person? Gender doesn't really matter as much. 

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An interesting question that made me think, since I never knowingly met a transsexual.  I consider myself 50% straight, 50% Lesbian but have a hard time wrapping my head around it.  Would that person be attractive to me?  Would I become disoriented by the mix of sexual characteristics?  I don't know.

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Hi,

you could to some users present on https://annuncigratuiti.online/trans for sure they know how to give you some advice. The only problem is that they speak Italian, but you use google translate can definitely answer you. the comments section is open so you can ask the questions you want. Please write in Italian otherwise they don't understand you; D

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On 5/4/2020 at 8:25 PM, NWAtlSwing said:

We have happened to play with two different male to female transgenders pre-op, who happened to be at parties we attended. They were fun, sexy people, who had different equipment. Very much enjoyed it.

Same here! Very fun and interesting. 

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On our 1st visit to a club and our 1st experience in the LS (yeah jumped in the deep end first time out) we spent the evening hanging out with a m2f trans guy great personality and into some wild stuff. We all ended up in a puppy pile and she ended up fucking a girl right next to me. We were new and didn't know what we liked and didn't like. But we BOTH regret not seeing if that could have gone further. She was very open and would answer any questions. We had never talked about it before hand. We both agree that should the opportunity ever arises again-we're game!  How much, if at all, I would participate RTBS. But I am keeping an open mind. ?

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On 6/1/2020 at 9:27 PM, couplers said:

I consider myself 50% straight, 50% Lesbian...

My wife is 60% straight and 70% lesbian.

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I fucked a transsexuals during a gay pride in San Francisco.  Oral sex and then he fucked me.  It was weird and cool.  He had boobs and a small bones, he was shaved smooth like me.  It was so damn naughty.  

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      Then, sensing it was time, Mike reached down and slid Jan's panties off, and then lowered his own underwear, his fully erect cock standing straight out. Again, the two heard a slight moan from Irene's side of the room. Jan reached down and began to stroke the length of Mike's cock with her hand, then slowly kissed her way down his neck, chest, and belly until his cock was pointing straight at her mouth.
       
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      He then led Jan a few feet to a couch, sat her down with her legs apart, and began to give back the oral satisfaction he'd just received. Kneeling in front of Jan he was able to fully access her beautiful wet opening. He glanced up to see that Jan's eyes were closed and she was pinching her nipples with her hands.
       
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      When Jan opened her eyes momentarily, she saw what was happening. Seeing Irene behind her husband, knowing the two were also fondling each other as Mike continued to do such an excellent job on her wet pussy, was too much to take. Jan began what would be a very long climax. As she came down the sensation of Mike's mouth was too much for her sensitive clitoris, so she pushed his head away. When Mike glanced up at his satisfied wife, he saw her smile and motion for him to turn around. Mike smiled back and whispered, "I love you." Jan mouthed the same words back, then added, "enjoy her."
       
      Mike turned around, pulled Irene to him, and met her lips with his. She kissed Mike deeply, and her small tongue explored his. He felt her firm tits against his chest and sliding his hands down her sides, felt her slender waist and then her nice hips and ass.
       
      After a long passionate kiss, Irene again reached down and had Mike's cock in her hand. Mike managed to undo Irene's belt and worked her skirt off and under her knees on the floor. Now he had better access to her nice ass as he slipped his hands inside the back of her silky panties.
       
      They continued kissing and exploring each other's bodies. Jan sat on the couch and watched as her husband, just a few feet away, was savoring this young woman's body. In a way, she felt a twinge of jealousy but remembered the times that Mike had allowed her to enjoy a moment with other men, and how it was just that, a moment of enjoyment. Then, with the jealousy changing to erotic stimulation, she relaxed and enjoyed the view. Irene was sexy. Mike was very sexy... and her's!
       
      Mike was amazed at how talented Irene's hands were. She seemed to know exactly how to stroke his throbbing cock. He began to release Irene's ass and move his hands around to her front. One of his hands came up to one of her nice firm tits, and he squeezed her hard nipple. He felt her groan into his mouth. His other hand began to work its way down her hard belly towards her pussy. But, just as he felt her soft pubic hair, one of her hands stopped his. "No, no, more there," Irene muttered, breaking their kiss momentarily, "on ass. Like hand on ass."
       
      As Irene spoke, she had taken Mike's hand and moved it back around behind her and onto her nice ass again. Mike didn't mind. Irene had a wonderful body, great ass, and really nice tits. But, after a while, Mike's need was too great. He broke their kiss and turned to look at Jan questioningly. Jan smiled and nodded her ok to her husband. She knew Mike and knew that he needed to fuck to truly finish. But almost as soon as Mike and Jan had decided, Irene intervened. "No... please... you two make love." As she spoke, she broke partly away from Mike and tried to turn him back towards Jan. The move was quick, but not quick enough to hide what Irene intended to hide.
       
      Mike looked down at Irene's panties with amazement. Jan, seeing Mike's astonishment, looked as well. Irene's panties were distended out from her feminine body. Irene looked embarrassed and tried to turn away to conceal her predicament, but Mike grabbed her shoulders softly and stopped her. Mike knew at once, as did Jan. They had often seen, and enjoyed seeing, photos of transsexuals. Nothing said would have put Irene at ease. So nothing was said.
       
      Mike helped Irene to her feet in front of him. Mike's cock was in desperate need, and Jan knew too well what it needed. Jan moved her ass closer to the edge of the couch, allowing easy access for Mike's hard cock. Mike walked on his knees the short distance to the couch, pulling Irene with him, and easily slid his cock into Jan's wet pussy.
       
      Mike then reached up and slipped Irene's panties out and over her erect cock and down her muscular legs. Jan leaned forward, and while being slowly fucked by Mike, took Irene's cock into her mouth and began to suck. She looked at Mike, whose face was just inches away, and grinned devilishly. Mike took the dare and began also to lick Irene's cock and small testicles as Jan continued sucking. Irene was pinching her own nipple with one hand, and with the other reached down and explored one of Jan's large breasts.
       
      Mike began to fuck more purposefully as his need became too much. Knowing Mike's movements meant he was near, Jan released Irene's cock and allowed Mike to take it into his mouth. The feel of Mike's cock in her pussy, the feel of Irene's hand on her tit, and the sight of Mike sucking this young woman's cock was too much, and Jan began another strong orgasm. Mike felt Jan's pussy pulsate around his cock, felt the wetness turn to the squeaky-clean sensation that indicated a woman's orgasm, and then tasted the first small squirt of what would be many larger ones from Irene's cock into his mouth.
       
      Mike started to cum, filling Jan's pussy with more cum than he thought he'd ever given in one session. As he continued shooting his cum into Jan, he kept feeling Irene's cum shooting into his mouth and throat. It was a very unique, a very exciting, a very damn good feeling.
       
      "Wow! That's unbelievable!" Mike heard Jan exclaim. Mike knew it was Jan's voice but had never heard her sound quite like this before. Her voice was husky, smoky, and coming from somewhere raw and deep inside her sexual psyche.
       
      Mike kept his cock in Jan and kept Irene's cock in his mouth for a very long time after they all had finished their climaxes. It just felt right. Jan had said it all for all three of them. It was just unbelievable. And they all three knew for certain that it would also be... Unforgettable!
    • By Galanga
      Ok, here’s moral puzzle for you to ponder involving honesty with anonymous sex partners. At swingers clubs you meet guys all the time that claim to be firemen, Navy seals, surgeons, etc, and you meet men and women that claim to be 35 when they’re clearly over 40. Many couples fib about their experience level, weight, dick size, careers, etc., to try to snag a shag in the backroom. I feel this is ok, and to some degree even expected. But here’s a “misrepresentation” that may raise a moral question for some, and I solicit your opinion.
       
      We have a girl-toy who loves the adult theater/dogging/gloryhole/gangbang scene, and that’s why she occasionally hangs out with us on our adventures. She’s drop-dead gorgeous – a natural beauty with thick long blond hair, small but perfectly shaped breasts, long silky legs, and a killer ass. She stands over 6’ tall with her 4” pumps, and knows how to dress to ooze out every morsel of her sexiness – apparel that is so intimately linked with her sexuality that she never takes it off no matter how many guys are in line for her. Her voice is eerily seductive sounding more suited for a fat black Gospel singer rather than an Arian looking girly-girl.
       
      Her facial features are stunning in their breadth and depth with giant sparkly blue eyes, a huge smile, and large puffy lips. Under her baby smooth skin is a layer of chubbiness that perfectly fills out her curves and gives her softness to the touch that magnetizes men’s hands. When guys look at her their jaws drop like that of a broken ventriloquist dummy. Whereas most adult theater girls prefer it from behind (no intimacy, highly depersonalized), she fucks face to face at adult theaters, and when she reaches those long legs out to the next guy in line and closes them around him like a Venus Fly Trap his face floods with that “this is too good to be true” look. And all of this beauty is natural with the exception of some cosmetic surgery she had on her neck.
       
      She’s in her 40s, but she looks about 25 … and allows everyone to think that. But that’s not the big lie. The big lie is that she’s actually male. She lives as a woman, and there is absolutely no way to tell she’s not genetically female just by looking at her … unless you look at the right spot. The only masculine feature she has is a penis and testicles. She is so convincing that she works as an erotic dancer at a bi-friendly club. At swingers clubs and adult theaters, I watch in amazement as she takes a guy face to face, her legs wrapped around his back like lobster claws, his hands roaming everywhere on her body, and French kissing as he fucks his way to paradise, without the guy ever knowing that he just came in a shemale’s ass rather than a woman’s pussy. And she’ll do this some 20 times in a row at such venues. That’s a big part of her enjoyment – knowing that the guys think she’s a genetic woman.
       
      How is this possible, you ask? Well, first of all she’s not gay and not bi. She self-identifies as a female born in a male’s body. She began cross-dressing at around 5 years old because being a girl “felt natural”. She always looked like a girl, and always conducted herself like one. She had her first sexual experience at age 12, giving a blowjob to a handyman working at their home. He thought she was a girl, something that excited her more than the sex itself. It was then that she decided to officially change her gender. Fortunately she had supportive hippie parents who allowed her live as a girl outside of school. Ridicule and bullying forced her to drop out of high school. Then she lived as a girl permanently. When she turned 18 she began hormone treatments, had her Adam’s apple fixed, and legally changed her name to a female name (which I will keep secret, but for this post I’ll call her Sally). 25 years of hormone treatments have shaped her already naturally unmasculine body into that of a super female, yet she still has testicles … and they produce large amounts of testosterone, giving her female sex drive an aggressively male edge.
       
      Ok, but what about the cock and balls? How does Sally fuck face to face wrapped around a guy fucking what he thinks is a woman’s vagina? Well that’s done with a brilliant piece of modern technology. By outward appearance it looks like a sexy corset. Like many corsets it has a cloth crotch strap that starts in the back, goes down between the butt cheeks, loops between the legs, runs up the front, and laces just above the tummy. And, like many corsets, the crotch strap has a slit cut in it so that intercourse can be performed without having to undo the strap. But unlike regular corsets, this crotch strap is specially designed to firmly tug the scrotum and penis upwards towards the belly button. Under the corset there is a second strap that secures the scrotum and penis against the belly. The front part of the corset where the crotch strap fastens is lined with thick foam pads that surround the cock and balls, eliminating any bulge. Attaching a feminine napkin to the inside of the crotch strap will prevent an ejaculation from soaking through the corset.
       
      Try this guys – tug your scrotum up towards your belly button and use a mirror to look between your legs. What you will see will amaze you. The skin on the bottom side of your scrotum melds into the bottom of your butt crack and looks very much like vaginal labia. Now if that structure was under a crotch strap with a slit in it, what would appear through the slit would very closely resemble a woman’s vagina. And if you stuck your finger in the slit it would slide right up between the bottom lobes of your butt crack which, with proper lubrication, would feel like a vagina to someone who’s expecting a vagina. The illusion is so convincing that a man might even go down on her without knowing, although she never allows that risk to be taken.
       
      Thus, when Sally is about to be fucked, she wraps her legs high up on the man’s back, raising them almost vertically. This puts her anus directly into the penis’s thrust line. So when he pushes in, the penis goes between the bottom butt lobes and travels about 1 inch to penetrate into the rectum. Just to assure a very astute fucker doesn’t notice the subtle differences, especially in tightness, she distracts him with very passionate French kissing throughout. Fucking in this position has the added advantage that the man’s thrusting grinds against her belly to belly, and therefore grinds against her cock, assisting in the induction of her own orgasm.
       
      I have watched her ruse work at adult theaters, dogging sites, and at a swingers club that has “gangbang” nights. She always goes to venues with subdued lighting and frantic guys. She goes dogging at night, which even makes me a little uneasy. Never goes to a house party, or anywhere “high risk”. For Sally, “high risk” means high risk of getting “outed”. For her, a huge part of the excitement is being taken as an actual woman.
       
      So, what do you think of this misrepresentation? My husband and I never blow her cover. We play along with the ruse. My very non-gay husband even fucks her on occasion to “break the ice” for the group. What do you think of us playing along with her ruse? I noticed in another thread many couples felt compelled to “out” a person with an STD. Does this moral compunction extend to outing a gurl? Should a sense of honesty outweigh loyalty to a friend? And if “body misrepresentation” is a moral issue, does this extend to women with breasts implants? Or men with cock rings?
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