As always this is a longer post with some back-story because even the quickies in my life seem to have a story behind them. If ypu want yo skip to the sex (guys), scroll down to the obvious marker(.
I hesitate to post this because of all the judgment that will come with it, but what the heck, here goes.
~1997
As a late 20s something staff sergeant in the Marine Corps, I was stationed in an east coast city in the US South whose greater metro area spanned seven counties. The city is known for the number of colleges with Greek systems on the various campuses. I was dating a girl named “Tonya” who was about 4 years younger than me and a senior at one of the universities. She was from the same state, but not the city that she studied in. Tonya was a really cool chic who had attended Marine Officer’s Candidate School (OCS) through one of the Marine commissioning programs and was waiting to graduate so she could start her military career. Tonya was shorter than me by a few inches, and had a rockin’ athletic bod with great augmented boobs and a nice round ass that you could bounce a quarter off of. She was a natural blonde with a sexy tattoo of a rose vine that started on her back, crossed over her right shoulder and ran down her chest and cupped under her right breast. Her pussy was always clean shaven, soft, and smelled of body powder. ❤️
Tonya and I had been casually dating for about 6 months. We were exclusive, but emotionally detached because we both knew that once she commissioned we’d likely follow different career paths being that she would be an officer, while I was an enlisted man. (For reference on this subject, see my other story about me and my company commander). In addition to our disparate ranks, I am an infantry Marine and she absolutely would not be since women weren’t allowed in the combat arms until almost 20 years later.
One warm Friday evening Tonya and I went to a neighborhood bar in a suburb town of the big city. We liked this place because it was laid back and had an outdoorsy backyard feel. This particular night the place was about half as busy as a normal Friday. We were sitting on the patio playing Quarters with shots of beer instead of liquor. An hour into the evening our waitress asked us to cash out because she was going off shift. I paid the tab, but we chose to stay. A few minutes later another waitress came to the table and introduced herself as “Joanna” (Jo for short) and told us that she would be taking care of us for the rest of the evening. The woman was very flirty, which added to the night’s vibe. She was mid-20’s, about 5′ 5″, 115 lbs (+/-), and had overly large boobs for her frame. And a cute littke ass perfectly framed in jean shorts. She was a certified hottie. We ordered another pitcher and she hurried off to the bar.
When Jo returned with the pitcher, she asked Tonya where she was from, and what high school she attended. As it turned out Jo graduated from the same school, but a year ahead of Tonya. Tonya admitted that she was a science nerd and wasn’t very social in high school, and was a late bloomer. Jo said that she remembered Tonya, which really got my girl thinking.
For the rest of the evening Tonya tried to remember Jo but couldn’t place her. She said that she looked vaguely familiar, but couldn’t comfirm a point in time where they met. This was in the early days of the internet and waaay before social media, so it was her memory, or nothing. She came up with nothing.
Midnight came and we decided to move along. We’d been there since about 8pm and the night was still young enough to hit one more bar before going home. We weren’t drunk, but we’re tipsy enough that we took a cab. Jo brought us the check, I paid and we got up to leave. Tonya asked Jo if she wanted to exchange numbers so that they could reconnect. Jo eagerly gave us her digits by writing her number in Sharpie on Tonya’s palm. Tonya wrote her number on the receipt and said that she’d call her. I definitely picked up on an obvious flirtation, and it wasn’t with me.
The rest of the night was uneventful. Tonya crashed at my house since her car was there, as we had left my truck at the bar. Saturday was lazy. We hung out at the house all day, lounging in our sleep clothes; me in a pair of boxer shorts, and Tonya in one of my college sweatshirts. The day went by and we decided to go out again, this time for dinner and a movie. We taxied to Sidelines to pick up my truck and when we arrived we saw Joanna in the parking lot going in for her Saturday night shift. Tonya hollered her name and Jo came over to where I was parked. The girls hugged and we all made small talk for a few minutes before Tonya told Jo that she still can’t place her.
Jo laughed and said, “You really don’t recognize me, do you?”
Tonya admitted that she didn’t, to which Jo responded that, “We hooked up once!” Tonya immediately denied this, as she wasn’t bisexual in high school and at that point had never dated a women, much less “hook up”.
Jo replied, “Well… I was a boy then and my name was Joe!” Smiling coyly, she (He?) turned around and quickly walked towards the bar, looking over her shoulder and giving Tonya a smile. Both of us stood there stunned watching her cute ass sway as she walked away.
Did I say that Tonya and I were both stunned? I think Tonya was in shock actually. She looked at me with big eyes and an open mouth and immediately recalled the event, a one night stand that she had with a guy named Joe after a football game in her Junior year of high school. Apparently, she and some of the science nerds went to an after party at one of the band geek’s lake house just outside of town. Joe was there and apparently they hooked up. She said that it was a drunk, sloppy, and quick encounter; nothing at all memorable or to be proud of. By her account it was awkward and uncomfortable. She said that “Joe” was shy and unskilled, which for her was a statement because she herself had not been overly sexually active until mid-way through university. And now, her high school hookup was not even a man, but presenting as a woman. WTF?
Keep in mind that I am an old man now. This event happened over 20 years ago when being Trans wasn’t as common as it is now. This person, Jo/Joe had definitely gotten some work done, which explained the too big for her body boobs. 🤔 in addition to the implants, she had grown out her hair into long curly auburn locks about halfway down her back. Not even an Adam’s Apple. This dude definitely transitioned into a woman as much as one could from a third person perspective.
After a few minutes of standing there wondering what to do next, we got in the truck and went to dinner. I’d be lying if I told you that I remembered what we ate. I do remember that it was a seafood joint down by the large river that ran through the northern part of the big city. I do remember that the conversation was centered entirely on the conversation in the parking lot.
Tonya just could not believe that a guy from her small conservative home town had transitioned from a man to presenting as a woman. And, as it usually is with women, she began to over-analyze the situation. Clearly he was gay back then, which was not uncommon, even in her town. His awkwardness during their hookup was clearly an attempt to be a stud when he clearly was not. Halfway through dinner, she chose to give Jo a call and left a message, saying that she was trying to process what was said earlier and that she had questions. We finished our early dinner and went to the movie. With all our drinking the night prior we chose to keep it a low key, alcohol free evening.
I do remember the movie. We saw ‘Fools Rush In’ with Salma Hayek. Nothing else matters about that movie except that Salma was in it. Salma became my “celebrity boink” crush that night and has not been replaced by any other actress since. ❤️❤️❤️ It’s funny what the mind remembers. I couldn’t remember dinner, but I can remember in vivid detail the movie we saw afterward.
After the show we decided to go to her house since we crashed at mine the night prior. As I was pulling out of the parking lot Tonya turned on her phone and got a voice-mail notification (1997 was before texting was mainstream). She called her VM and heard a message from Jo, who had returned Tonya’s call while we were in the movie. Jo mentioned that she got off at 10pm and invited Tonya to call her back after then. It was almost 11pm now, and not long after Tonya listened to the message, and listened again, Tonya’s phone rang. It was Jo. Tonya and Jo chatted and Tonya said that she had questions. Jo apparently asked that they get together to discuss in-person, to which Jo agreed. Covering the phone, Tonya asked if it would be okay if we invited Jo to her house that night. My response was quick, “It’s your house!” Tonya then asked Jo if she wanted to come over and Jo accepted.
When we got to Tonya’s apartment I walked her to her door, expecting that I’d leave her there to have her conversation. Tonya immediately told me that she wanted me to stay for moral support.
About 30 minutes later, around midnight, Jo arrived. When Tonya answered the door to let Jo in, wevsaw that Jo had clearly gone home to change. She was wearing a low-cut, long-sleeved blouse and faded denim mini skirt cut halfway up her thigh. She was made up and, again, looked totally female, cleavage and all. Tonya invited her in and offered her a drink, to which Jo readily accepted saying that needed some liquid courage for the conversation that she knew was about to come.
We all sat at the kitchen table started sipping our beers. There was an awkward silence and the air in the room dripped with tension.
Tonya broke the silence by asking, “Why?”
Joe said, “I have always felt female. I was diagnosed with gender dysphoria in college and started hormones a few years ago.” That exchange broke the ice and the conversation flowed from there.
Tonya asked, “Were you not happy just being gay?”
Jo responded with, “I never was gay, I considered myself Bisexual, as I always liked women but liked sex with men as well. And I still do, so I guess I’m still Bi,”
Tonya… “Ummm, what?”
Jo, “I was a woman in a man’s body. I liked women, and I liked men. Now, I am a woman in a woman’s body with something extra, and I still like men, and I still like women.”
(Jo asked for another beer)
Tonya whispered, “Do you still have a penis?”
Jo laughed and blushed and said that she did, that she couldn’t afford that surgery. she also explained that Trans women who have their male genitalia removed and replaced with a constructed vagina can’t have an orgasm, and very much loves to have an orgasm.
Tonya asked if “it” still worked?
Jo replied that it did, but with the hormone blockers and estrogen, it was not as big as it used to be.
I could go question for question but I won’t. The conversation lasted an hour and a full 12 pack of Coors Extra Gold, which was a popular beer back then. After the beer was gone we shifted to whiskey. The more tipsy we got, the more graphic the questions became. Tonya would ask about Jo’s experiences with other people, and Jo would answer. The questions ranged from how Jo’s family accepted her transition (they didn’t) to how she interacted with everyday people. With the exception of a feminine, but gravelly sounding voice, no one would know by casual conversation that Jo was a guy. Or… WAS a guy, as it were. Jo said that everyone at her work thinks that she’s a genetic female, and she let’s them believe it.
Tonya asked about her boobs, to which Jo asked, “Do you want to see them?”
Before I go on, let me explain that through this whole exchange I was a fly on the wall. A spectator to this drama that unfolded at the kitchen table. With the exception of being the beer guy, I contributed nothing to this conversation. I was simply drinking and watching these two chics talk about the last five years of Jo’s life. Other than shared exchanges between myself and Tonya, and shy, coy glances between me and Jo, I was not even there.
So, back to the boobs! Tonya quickly accepted the offer to see Jo’s boobs. So Jo drops her blouse over her shoulders to reveal two beautiful tiddies held captive in a white lace bra. At this point I’m wondering if I should even be there, but neither of them are paying attention to me. Jo reaches back and unsnaps her bra and it falls away to reveal two beautifully crafted porn star level breasts. If I remember her statement correctly, she said that she had a great surgeon and that, “God didn’t invent plastic surgeons so they could starve!” 😄
Almost immediately Tonya asked if she could touch them and Jo responded with a head nod. Tonya got up and started squeezing them and noticed that there were no scars. Tonya also had implants, and knew what to look for. Apparently Jo’s doctor went in through the armpit to avoid the nipple and underboob scars that are typical of breast implants. After a few more moments of admiration, Jo put them away and pulled her blouse up.
At this point I had had enough for the night and excused myself to Tonya’s bedroom to go to sleep. The girls stayed in the kitchen and continued their discussion while I quietly jacked off in Tonya’s bathroom thinking about what I’d just seen, my girlfriend fondling the tits of her onetime male hookup from high school. I was so confused, and drunk, and I couldn’t have felt any more awkward, but I came hard. When I say “hard” I mean that I think I spray-painted the ceiling! 😳 It didn’t take long for me to drift off to sleep after such an intense orgasm.
At about 2:30am Tonya came into the room and woke me up, telling me that Jo had left. Tonya was clearly feeling some kind of way and turned on by the conversation with Jo. She started rubbing ny cock, which immediately responded to her touch. Tonya started to tell me about the rest of their conversation which was centered around Jo’s sex life post transition. About how Jo is a “switch” in that when she’s with men, she is sometimes the submissive, and sometimes the dominant. When she plays the Sub, she is totally submissive to her man in every way and let’s him have her ass and mouth; but when she switches to a Dom, she absolutely fucks her man’s ass and makes him suck her cock. This clearly intrigued Tonya and she seemed to have hung on every detail of the conversation between herself and Joanna.
She then started talking about Jo’s interaction with women. Apparently, because Jo still has a dick, she’s always the dominant partner the same way she would be if she were still a man. Apparently Jo likes to kiss women, lick thier pussies, and of course… fuck them. It was obvious to me that Tonya was curious about Jo in more ways than reconnecting with an old friend. Tonya stopped talking and started sucking my very hard cock, vigorously. She was so horned up that she couldn’t control herself. Alcohol usually made Tonya horny, but this night she was off the charts. Lucky for me I had already cum an hour earlier, so I had plenty of stamina and an empty ball sack so I easily resisted another orgasm. Tonya stopped sucking me, and climbed on top Cowgirl style and started to ride. I loved fucking her in this position because I am very much a boob man and am transfixed on her perfect boobs as they bounce in front of me, partially framed by her long blonde hair and sexy AF boobie tattoo!
Tonya was a squirter. Her first orgasm always soaked my crotch as the warm liquid shot from her pussy. This time was no different. As was usual for Tonya, once her first cum shot was released she would want to switch positions. I got up from under her, and she got down on all fours. Once I was positioned behind her I would rub my dick up and down her pussy slit from her asshole to her clit, teasing her. This usually drove her nuts and this time was no different. As I was sliding my cock down to her clit she lurched backward at the perfect time and impaled herself on my cock, all the way to the hilt. She let out a loud moan and immediately dropped to her elbows and buried her pretty face in her pillow. This is another favorite position if mine. I absolutely love looking down at her beautiful ass as my cock strokes in and out of her pussy. As I said earlier, Tonya had an athletic body and the muscle tone in her back was absolutely perfect. She had a round bubble butt, a small narrow waist that created a perfect V through her lats up to her muscular shoulders and the beginning of that sexy rose vine tattoo that began under her right shoulder blade. 🔥 This was a position that normally guaranteed an orgasm from me and another from her. After maybe ten minutes of hard stroking she came again. I remember how her vagina pulsates when she cums, as if she were milking my cock. This time was no different, except that I wanted to see her face. As I felt what was left in my balls flow up to the tip of my cock I pulled out and flipped her on her back, just in time to cum all over her beautiful tits and face. I think I shot three decent ropes before it started to dribble. Tonya leaned forward and took my dick into her mouth and drained what was left into her throat.
This was never the end. Tonya laid back on her pillows and guided my face to her tits. It wasn’t long into our sexual relationship that Tonya very clearly made it understood that if I made a mess it was my job to clean it up, and she didn’t mean with a wet wipe. Tonya fully expected, and quite surely deserved, that I would clean her up with my tongue. Her tits, her neck and what had made it onto her face. This always ended up with the most passionate of deep kisses as she craved the taste of my cum, from my mouth into hers. I don’t care what anyone says or thinks, it was worth it and I dug it.
Tonya is the reason why I started drinking so much Pineapple juice by the way. Because if you know… well, you know.
We fell into each other’s arms and quickly drifted off to sleep, spent
(This is where I will end Part 1. There is more to this story, but it deserves its own post. Stay tuned for Part 2. In the meantime feel free to read some of my previous true life experiences, some of which might add perspective to something you read here.)
Source: reddit.com/r/gonewildstories/comments/v2odqo/a_man_a_female_and_her_m2f_trans_exboyfriend_part
Pineapple juice? Do explain? I don’t know lol.
Your stories are wild and I love them, bravo 👏