- Transgender & Crossdressers
- My Second Time
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I hope you've been enjoying my previous stories thus far. As you know (unless you HAVEN'T read them) my stories are short, true, and to the point, so you may enjoy them that much quicker without reading long drawn out writings. So here is another true story for your enjoyment.
This was my second time (well, technically my third, as the first guy fucked me twice within ten minutes). From back in the days of placing ads in the personals section of a local paper (the youth of today has no idea what the pre-smartphone era was like), this story takes place. It was somewhere around '96 or' 97, and not too long after the first time. I was married to my first wife at that time, later becoming my ex (but ironically, we got divorced because SHE cheated on ME, having had no idea that I was cheating on HER, by getting fucked by men while dressed in women's clothes. But isn't it cheating only if it were another woman...?).
So, having really (REALLY) enjoyed my first time, I placed my ad in the paper, and waited, and hoped for, the replies to start coming. Of course I received plenty of replies, just not many serious (or sane) ones. But alas, finally, after a couple weeks if I recall, I got one that I went with (who agreed to meet and could host, the latter of which was, and still is, a must). He lived alone, was about the same age, and was close to where I lived. The shorter the time away from home the better as to not arouse too much suspicion. He was also a crossdresser, which peaked my interest even more.
For the week prior to the agreed upon date, I was nervous as hell, just like I had been leading up to my first time, and every time thereafter. The nerves never go away, it feels like the first meeting every time. You just don't know what you're getting into until you get there. I've had sex with 19 men to date, the next one will be number 20! Hoping to make this happen very soon, but unfortunately, sometimes the dry spell lasts a year or more. That's not good, but thank goodness for porn and masturbation. And thank goodness for Craigslist too! Sure wish they'd been around back then; I'd be WELL over 19 by now. But better late than never!
So the day finally came. The day dragged on at work, of course, the anticipation of what would happen later that evening predominantly occupying my mind. I had again made up another story about helping a friend or meeting some guys from work. I had to keep my stuff hidden away, my first wife knew but disapproved of my dressing. So I kept my stash all stuffed away in my toolbox in my basement. We lived in an apartment and had a shared basement, and I would often go down there and change, sneak over to the other side of the basement (someone else's space, so quite risky but so much more erotic), and rubbed one out. Left a lot of DNA in that basement, never getting caught, but came real close a couple times. Just adds to the thrill, and a much more powerful orgasm!
But on this day, my stash would make it out of the toolbox and into my car for an evening out. Following the directions he gave me (no GPS's back then either, I'm feeling old), and arrived at his apartment. I rang the bell and he buzzed me in. It was a two-family unit, he was in the upstairs apartment, and was waiting atop the stairs dressed in a hot minidress, nylons and high heels. We went inside, he saying he couldn't wait to see me dressed. We talked for what seemed to be too long (I wasn't there to talk), before he finally suggested I change in the bathroom. I changed into the same red velvet dress I wore during my first time, a purple teddy, black fishnets and black 4" strapped sandal 'fuck-me' shoes.
At this point, I had very little experience, as this was only my second hookup with a guy. I asked if I could ride, he agreed, and I tried. I got on it but it was too painful (now I can ride a baseball bat but not back in the early days). We moved to the floor and I got on all fours. He entered me in what was to be my very first doggy fuck! It hurt as well, but I was going to go to the end. No matter how much it hurt, it was still an amazing feeling, a big cock stretching my asshole to the point of never before. In and out, I couldn't wait for him to finish, and at the same time, I hoped it wouldn't end!
Eventually (and sadly as well) he came, his cock pulsating in my ass, I could feel it against the ring of my anus. I told him I wanted to fuck him now, but as with most guys, nobody wants to GET fucked after they cum. I look forward to the opportunity to GET fucked AFTER I fuck someone else. I guess it's called 'flip' fucking. I so love getting fucked that I'd have no problem doing that. So as usual, I took care of myself, but certainly was not leaving disappointed! There have been plenty of hookups that WERE disappointing, a 'failure to launch' type of thing, but the majority of my hookups have been successful and memorable, and I'm glad to finally share them with other like-minded people. It's nice to be able to be honest, to share my life experiences, and not be judged as society judges people who engage in this type of lifestyle. They just don't know what they're missing!
As always, I hope you have enjoyed reading. This was as accurate as I can remember, being so long ago. I might follow with another story if I get enough requests to do so. Thanks to everyone who has read my stories, and special thanks for the kind positive comments, I'm glad you enjoy what I share with you!
- COMMENTS
Anonymousabout 3 years agoMy first time getting fucked did not go well for me at all.I had never been fucked before and tryed to act like i did all the time wrong.His cock was to big for my ass to take.He had a super monster cock 8'' soft by 4'' round.It tour up my ass both going in and coming out.He filled me with so much cum it ran out my ass down my cock and balls to my leggs.But he pushed it back in and fucked me again to the point i was going to pass out.When finished i could not walk i had to be helped to my car.
Anonymousabout 4 years agoLoved your story! Have wanted to be screwed for awhile now. It's all I think about some days! You're so lucky!
Riki1942about 4 years agoI just read your story again. This time I added it to my favorites so I could find it again.
I already made a comment, but I wanted to add something. I know that feeling very well, the one where you want so much to feel him cum in you and, at the same time, don't want it to be over. Also, I know what you mean about the feeling of his cock pulsing in your ring. My boyfriend and I bareback. When he cums, I can't actually feel his load spurting inside me, but I do feel his cock pulsing in my ring as it is stretched around him. I love how he makes me feel stuffed but, the part of me that actually has the touch sensation is my ring and I love the feeling of his cock throbbing in me. I like him inside me and still hard when I cum too. That feeling of my ring clamping down on his hard cock when I cum is almost like having two different types of orgasms at the same time.
Riki
Riki1942ralmost 7 years agoI cross dress too and I love wearing latex outfits. I know just how you feel. I'm mostly a Bottom so I don't mind at all if my partner never wants to be fucked, but I hate it when a guy cums and loses interest in sex. I love getting fucked even after I cum! I have never had much of a problem taking a cock but I know what you mean about it getting easier to get him in after getting used to it. I have been fucked many, many times more than nineteen but, when I know that I'm going to be doing it, I still wear a butt plug for a while first. When he pulls it out his cock slides right in. I have a steady partner now and we do it bareback. I just love being able to have his cum inside me when we fuck!
Anonymousabout 8 years agothe second time I had a man was a year ago it was a older man I pick him up he was walking on the road I ask him if he want a ride he said yes that be nice he got in the car and close the door as we were driving he look at me and smile he ask me were I was going in town why I just live up here a bit you can drop me off at my place as I turn to look at him he smile again this time I knew why my shirt came open and he saw my bra a bit I went to do it up he said that all right I seen men in bras before then he said turn up in this road and pull into the drive way I did as told and part the car he ask how about a cup of coffee for giving me a ride I said sure why knot we went in and I sat down on the couch he came with the coffee and when he bend over he was looking at my bra I said here let me put the cup of coffee and when I did he saw my bra more that when he said may I see your bra and feel it I said yes sir do you want me to unbutton it or you want to he start to undo my shirt he said I have a lovey bra and why are you wearing one I told him a lie I put it on for a joke I was on my way to see a friend well are you in a hurry I said no he can wait a bit he then put his hand on my bra and pinch my nipples as he did my hand touch is crotch he pull out my breasts and I work open his fly and pull out his cock well the next thing I was sucking his big cock yes he said it been a long time since I had my cock suck after he came he remove my shirt and pants and look at my ass hole have a cock up your ass I told him a long time ago well then let me give you my cock he just shove his cock in my ass hole I yell yes give me your cock i want it all he told me that what you get and more if you think you are going to your friend to night your worry well I guess I am knot then well that night I stray with him and in the morning he ask if I want to go I lie and said no sir I stray a bit longer that my girl now come back to bed and when I did he told me you are mind girly bitch now he turn me over and shove his hard cock back in my ass hole he said girly this the best pussy ass I had in awhile as he said that he told me since you like to dress in women clothes you will be in them well after a week I move in with him became his girly bitch
Riki1942over 10 years agoYour comment about how some guys loose interest after they cum is interesting because I know what you mean. I, like you, am always ready for more and have had a few friends that still want to play after they cum. Sometimes they spend the night and fuck me more than once.
I love to cum while I am being fucked and, although it does take some of the urgent edge off, I still want to be fucked more. It's great if you can get the guy to take a Viagra and he still wants to play after he cums, because it's much easier to keep him hard and inside you.
Riki
jrbradford64over 10 years agoI loved the more detail in this story. But I want to know how you feel as woman and how you want to be treated. Do you like oral sex? Do you like to show off what you're wearing to get your partner more excited? I can't wait to read more from you!!!
closetirvingover 10 years agoI just love your stories. I haven't hooked up in years. I would love to feel that lovely
feeling again of being filled with hot cum.
Anonymousover 10 years agohey when i was a kid i liked the tv series real mccoys with grandpapy amos
on the show grandpappy amos was always getting a visitor
in this story it's not grandpappy amos but grandpappy ANUS!
and all it takes is the right girlie clothes.
