Losing my virginity

hai my name's sophie! (check my profile for my stats and pics) and I'm a transgirl;) this story is about my first time.. well here goes

I'm not sure why I started dressing up as a girl but i remember finding some panties in a closet that used to belong to my sister. When I wore them I remember loving the feeling it gave me. It wasn't till I was 18, in college and sexually frustrated that I decided to become "sophie". I bought a high quality wig(for a decent price) and "found" some girl clothes in the laundromat (they fit me pretty well). I had a strapless flower pattern sundress, blue g string panties and leather boots with 4 inch heels. So I decided to buy a large black dildo (it had a suction cup). Every night I would lube up my asscunt and I would steadily work my ass against the wall while I pretended a real man was rocking his hips against my ass.

After a while I stretched out my asshole enough that I felt it was time I was ready for a real man. So I put up an ad on Craigslist and waited for a response. After scrolling through several prospects and pic collectors and I found one guy who lived nearby at a motel.
So I got all dolled up and walked over to my 1st "john". When I got there I saw a white male by the door way and he smiled when he saw me and let me in. As I walked in I saw a pretty lady talking to a guy on a phone. (the "john told me earlier in his emails that his wife is also a ts girl as well as a "working" girl. She was sitting by her computer while I sat on one of the beds in the motel room. She could see it was my first time by the way I was acting nervous around the couple. So she said that I should start by sucking her husband's cock. So unzipped his pants pulled out his 7inch dick he laid down on his bed. I slowly walked over to his bed and straddled him. Then I slowly bet over and gently licked and kissed his cock and balls. While I was giving her husband a blow job, his wife commented on how "she must really want that dick". While I was sucking his dick I felt the warmth of his cock along the inside of my cheeks. His manhood was pulsing and growing inside my mouth while I swallowed his shaft. after a while he told me to stop and his wife said that I should get down on all fours and lift up my dress and take cock fro a real man. While he was lubing up his dick she warned me that even she didn't like anal sex from him because his dick was too big for her. Right as she finished warning me he began slowly pushing his dick inside me. Luckily i had a lot of practice with my dildo so it didn't hurt as much as he started to pump his cock inside my asscunny. While pumping me full of man cum his wife started taking pictures of me while he had one last orgasm. After a while I felt his dick throbbing rapidly and after a long moan from the man who took my virginity he slipped out of my ass and he showed his cock to his wife who took a picture of his cock dripping in cum. He then said he was going to sleep and his wife said I was welcome to cum over anytime I like.
Publicerad av sophieluv
10 år sedan
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29
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leslie14
leslie14 3 år sedan
till darren134 : Hopefully itsmwhen wife at work 
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darren134
darren134 3 år sedan
till leslie14 : Cool good to know thanks baby. Ill give you a week in advants . Bi4now love Darren
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leslie14
leslie14 3 år sedan
till darren134 :  Sounds like  fun  we have to do it in hotel room 
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darren134
darren134 3 år sedan
till leslie14 : How do you keep that from her? And how often do you get to play ? I ask this im going on a motorcycle trip to Daytona in the spring and would love to stop bi for fun and games you know a little slap and tickle. Let me know  talk to you later bi sweet heart
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leslie14
leslie14 3 år sedan
till darren134 : wish I could i am merred and wife has no idea I a sissy ? ? ? 
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darren134
darren134 3 år sedan
till leslie14 : Hay sexy have you bin laid lately i sure wish you were in calif. I have a new cross dressing friend you would be a great fit with us .but i cant come there with my friend . And i still want to fuck that ass of yours and suck your huge clit . When was the last time you got any cock ? 
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leslie14
leslie14 5 år sedan
love it
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sub_guy_Sissy
sub_guy_Sissy 6 år sedan
Please write more about your experiences. They are so sexy!!
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ryancin69
ryancin69 8 år sedan
Wow, great story sounds like an incredible experience
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olybill 8 år sedan
what an amazing way to have your first time braver than me
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straightqueerblack
straightqueerblack 8 år sedan
wow..amazing indeed.
ur awesome.
wish my wife would bring a girl like you for me to fuck in the ass.
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SoraKH12
SoraKH12 9 år sedan
Amazing story!
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goose6920 9 år sedan
Amazing first time.
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Curious_Perv 9 år sedan
Even after all this time I love this story --- Wish I was in your dorm... would have been lots of fun
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sophieluv Publicerad av 9 år sedan
till leslie14 : I'm glad you liked it daddy :smile:))
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leslie14
leslie14 9 år sedan
beautiful story
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Curious_Perv 9 år sedan
till sophieluv : No need to blush sweetie anyone can put you on all 4s (as much fun as that is) it takes a real man to want you missionary and look into your eyes while pleasing both of you!!!!
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Curious_Perv 9 år sedan
Awesome adventure!!!! would love to see some of those pics!!!
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sophieluv Publicerad av 10 år sedan
till chevalier213 : aww thx! you're gonna make meh blush :wink:
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chevalier213
chevalier213 10 år sedan
That's a hot story, but I would fuck you face-to-face so I could play with your gurl-clit while my cock is sack-deep inside of you xoxoxo
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biwithnicehead 10 år sedan
Hot story Sophie!
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mykalsykes
mykalsykes 10 år sedan
Great story
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Biggie2 10 år sedan
mmmm your story make me so exciting and feel so horny i wanna have the same real story like you with you :smile:))) kisses
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robbieb13 10 år sedan
Sounds like a great time. thanks for sharing!
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jusenuff2
good story, would have loved to be him
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sophieluv Publicerad av 10 år sedan
I know! i was sooo nervous the 1st time
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TiLoBrown
TiLoBrown 10 år sedan
Sounds like a fun time. Good thing she was there to help you over come your nerves too.
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sophieluv Publicerad av 10 år sedan
I wish I had them too D: but I lost touch with them so i don't have them in my contact list anymore
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bicpl4u2pa 10 år sedan
Great experience! I'll bet everyone wishes you had those pics the wife took!:smile:
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