Out Of The Closet For One Night

About 5 years ago I traveled to Washington DC for a few days on business. When I travel on business I always take the opportunity to cross-dress, play with toys, and generally enjoy expressing my submissive feminine sissy side just for myself.

On this particular trip while scoping restaurants around my hotel I discovered there was a gay bar just three blocks away. As a married man who loves my wife, I would not do anything that would risk her health with an std. But I’d push the envelope. I decided to slip a butt plug in my ass, put on my thigh highs and panties under my pants, and head over to the gay bar.

Just the act of walking into the place was so liberating and I felt almost like an exhibitionist coming out to a room full of strangers. Of course nobody knew me so that made it even more exciting. I saw heads turn and felt eyes devouring my entire body as I walked to sit at the bar. I ended up chatting, flirting really, with half a dozen men that night. It was so sexy and exciting to sit in a gay bar and openly flirt with gay men. A number of men wanted me to leave with them but their intentions were a bit more intense than I was comfortable with.

I did leave with a nice older man who was married to a woman and had similar health concerns. We went back to my room and had fun using hands, toys, and did some mutual oral with condoms. We both got our sissy on that night and got each other off real good. Cuming hard together with another man was so exciting and hot. I’ve visited other gay bars since then when traveling but have never had such a perfect experience again.

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# 79236 - by Rimmy / May 22, 2025

by Anonymous on Jul 8, 2025 at 4:46 PM

I first cross dressed for a high school powder puff football game. I was the JV place kicker and despite my diminutive size I had a strong kick and deadly aim. My football coach saw me one day kicking a soccer ball in physed class and suggested I try out as place kicker on the JV team the following season. I did so I was on the team. Then my girlfriend, a year older than me and also a varsity cheerleader, told me about the powder puff tradition of the football players cross dressing as cheerleaders. We had two high schools in our town so we played each other for that game. I had waist length blond hair which is a bit on the wavy side so my girlfriend who was also friends with my older sister decided to transform me. It would not have needed much work as I was short (petite as my girlfriend calls it) slender and girly looking to start with. My girlfriend constantly told me how she loves to kiss my pretty face. I tolerated the word pretty because we didn't just kiss.

So the day before the game Mom took me to a nail salon to get acrylic nails. My sister obtained from someplace silicon inserts for my bra and she also loaned me an old bra of hers. My girlfriend loaned me other underwear and her JV cheerleading uniform from two years earlier. I was much smaller than my girlfriend. All three helped with my makeup that morning as the football players were expected to attend school in full cheerleader drag. So I went into school in pigtails, make-up, cheerleader skirt and top and knee socks, long acrylic nails. The only thing missing is my ears weren't pierced and my girlfriend suggested that next year we remedy that. Physed class was altered that day so none of the cross dressed football players had to get sweaty instead we stayed in the air conditioned gym practicing cheers guided by the girl's physed teacher. She half jokingly suggested I try out for the real JV cheerleader squad as I was easily as pretty as any girl on the squad and I actually knew all the cheers. My sister and girlfriend helped me with that all the preceding week.

We won both games, I think I got as many cheers from the crowd as the football teams did.

Halloween was about two weeks later and my girlfriend, sister AND mother absolutely insisted that we reprise our roles. So we went to the Halloween dance as football player and cheerleader and by then I had gotten my ears pierced at my girlfriend's insistence. That day in school was dress up day already so after school we went to my place, had a light dinner and then went to the dance. Then the next night which was Saturday we went to a Halloween party dressed the same way then we went trick or treating a few days later on the actual day itself and. I felt awkwardly too old for that but every time my girlfriend told the people I was really a boy they either complimented my costume and gave me extra candy or they accused us of lying to get extra candy. Many absolutely did not believe I was really a boy which was both embarrassing and exciting. That year they decided that the Sadie Hawkins dance was going to be full role reversal and not just girls asking out boys and that meant that all were expected to cross dress. My girlfriend was so excited. She picked me up wearing a suit and shockingly had gotten three quarters of her waist length mane chopped off. There was barely enough left to get into a short pony tail. My sister put my hair in a fancy updo and loaned me an old little black dress that no longer fit her and a pair of fake diamond earrings. I got my nails done again courtesy of Mom and wore heals again. My girlfriend couldn't stop kissing me frequently exclaiming how much she loved kissing my "pretty face." That evening is when she confessed to me that she was secretly a lesbian and dated me because I was naturally feminine looking and in her words, prettier than any of the other girls in our high school. That was quite a shock. She very adamantly insisted that she was not in any way attracted to boys and that was why she was attracted to me because in her mind I was a girl. That explains her constant use of words like pretty and lovely when she talked about me. I did not see myself as particularly pretty until Mom, my sister and girlfriend all femmed me up for the powder puff game and I looked at myself in the mirror and got an instant hard on. I literally wanted to have sex with the girl in the mirror. But her being a lesbian also explains why despite having dated her since I was a freshman we never got past second base. She let me feel her up every way possible and she loved grabbing my ass and kissing was an obsession with her but she never once tried to put her hand in my underwear. I figured it was due to being hung like a mouse (my sister's words) but in fact it was because I was hung at all.

So after Sadie Hawkins she started to buy me girlie g*fts as she called them. Shoes, outfits, make-up, perfume, accessories, pink curtains, bedding and rugs for my bedroom. She suggested I get my furniture painted white instead of brown and Mom and sis thought it was a wonderful idea to more fully bring out my feminine side. When I told Mom that my girlfriend had confessed to being a lesbian she responded with "I know, why do you think she is dating you?" Seems I was the last one to find out. Then Mom confessed that she NEVER really wanted a son an that my sister knew my girlfriend was a lesbian and had arranged the whole thing when my girlfriend saw my face and thought I was a girl.

She had decided she wanted kids and Mom wanted grandkids and so they all got together and decided that before it was too late I should fuck my girlfriend to make her pregnant. Mom and my sister took off for the entire summer leaving me and my girlfriend to be alone at my house and out of the blue I find her naked in the living room informing me that my duty was to make her pregnant as soon as possible. That did not make sense but when your beautiful girlfriend says "fuck me" you obey. She did though insist on dolling me up as pretty as possible, makeup, pigtails, nails and all then had me put on some frilly lace lingerie and fetish pumps way too high healed to actually walk in and she mounted me and impaled herself on my diminutive little dick. She said it was a relief to her that I was very small as she was a virgin and was deathly afraid of large erections what with being a lesbian and all. None of this made any sense but then I was thinking with the wrong head. By summers end she was pregnant with twins. Mom was so excited to learn she was going to be a grandmother. And that September was when I was informed that I would be taking hormones. By graduation I had full B cup breasts, all the usual changes and my girlfriend had completely gotten over her fear of erections since I stopped being able to get them.

We are still together. She proposed marriage to me a month after the twins were born. I decided not to legally change my gender so I would qualify for a spot on the football team. when I went to try out for place kicker on my college football team the coach laughed at me telling me that girls couldn't play on college teams. I showed him my driver's license and birth certificate and he still laughed at me then I made him a bet. I told him if I could not kick a field goal from the fifty yard line I would suck his dick every day for a year and if I could he had to put me on the team. He made a comment about hoping my mouth could handle equine endowment and laughed and told me to go ahead. I got the field goal and a spot on the team. He told me I was the prettiest player on any football team but I was sworn to secrecy as to how I got on the team. I never did suck his cock as it wasn't my thing at the time.

So today I am 29, I help manage my girlfriend's boutique, I have c-cup breasts and none of it plastic. I haven't had an erection in 13 years and my girlfriend is very happy about that. I don't miss erections because of all the side benefits of being married to a beautiful lesbian such as engaging in my favorite sexual activity, having her sit on my fact for hours at a time.

But recently my wife has expressed an interest in having sex with girls because she missed eating pussy. I don't blame her for that. She has also fixed me up with a really cute boy who is very girly looking and so I got advice from my sister on cock sucking and she gave me lessons by giving me step by step instructions while she watched and critiqued my progress and skill. The boy doesn't mind her being there. She reported back to my wife who also told me all about her adventures in eating pussy. I never thought I would enjoy sucking cock but I actually like it and I like kissing the guy as well. I still love my wife but now I'm glad we are cheating on each other as an expansion of our sex lives. I think I have it better than she does though. I still get to eat pussy every day. And I don't really mind that she likes looking at photos of pussies while I eat her to orgasm. But last night she said she thinks it's time I get rid of my little dick and balls and have them replaced with something she could pretend was a real vagina. I'm seriously considering it.

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Out Of The Closet For One Night

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by Anonymous on May 22, 2025 at 1:59 PM

by Anonymous on Jul 8, 2025 at 4:46 PM

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