Woman dating crossdressers

conscious cannon [deleted] says:

Hallo Eric,

since two month, I worked as a women in my profession as a teacher. And then I must make my administration steps to become a women: I have to change my name by court and so on. There is no time for a rendevouz.

But I hope, I shall find a man, who respects my female identity. Other girls told me, that this is not easy, but I will see.

It's a new period in my life and I enjoy it every day to be a women. May be, I will find a lovely man...

Excuse my english, but there is a lack of training...

Katharina
ages ago (permalink)

abundant play [deleted] says:

my first date with a man was a really pleasant experience . i met him thru another friend and i arranged a casual chat and coffee at my house .

he came over late in the arvo and i was a bit nervous at first thinking wat to expect but it was just a fun and intresting evening chatting like 2 friends who had known each other for yrs .

we still continue to meet for same thing weekly and occasionally go out for dinner to this day
ages ago (permalink)

ginany50 says:

My first date with a man was arranged by a mutual friend who knew that he wanted to go out with me. We met at a local coffee shop and talked for a while before going for a walk by the river.

It was a nice evening as it was the first time I'd been alone with a guy and he treated me as a woman, which was nice. He walked me back to my car where he asked if he could kiss me. I smiled and placed my hands around his neck so he could easily kiss me.

We went out 4 or 5 times and then just became friends. I still see him occassionally
ages ago (permalink)

lively muscle [deleted] says:

My first date was one evening long ago. I was at the Queen Mary's back bar when This handsome man dressed in a black business suit approached me ,and asked if we could have a drink together. We drank, we talked, and flirted with each other It was such a thrill when he began rubbing my thigh, and bottom through my dress. We danced a slow dance while he held me close giving me little kisses on the ear and neck. I was in a daze. Soon we were kissing some very sensual kisses. When he suggested we leave for his place I rubbed his cock through his slacks for the first time. As we road down Ventura Blvd toward the west, i sat next to him like a girl friend ,rubbing his thigh, pulling down his zipper, and playing with his wonderful cock. I was so looking forward having it in me...
89 months ago (permalink)

jessica_ricci66 says:

my first date seems like ages ago, but remember as though it was yesterday. i met him through a chat line, and after talking for a while i revealed to him i was in fact a cross dresser and could pass easily. this lead on to more conversation and he was pressing me to go on a date... i finally agreed. as we had planned to meet down by the lake in a public place so we could feel safe for the date. i wore my girly tight jeans and a white sweater with a pair of pink heels. of course i had on my sexy underwear and bra... i drove down to the lot and waited for about 20 mins when his black older sedan pulled up beside my car. i stepped out and got inside his car... when he began by saying OMG your gorgeous, i smiled leaned over and kissed him and thanked him for the compliment, rubbing his buldge which was OMG huge under his pants. he pulled me closer and we began kissing, he opened his pants and i began rubbing his cock, he started trembling and said he was going to cum, i quickly got on my knees on the front seat and took his cock in to my mouth, as soon as i went full deep he exploded with his hot jism and i drank every ounce and making sure he was done and dry.. i sat back up adjusted my bra... i asked him if would like to take me out on a real date, like dinner and a movie, he replied by saying "babe i have to go, please leave" i did without a word and never saw him again...
81 months ago (permalink)

imandi56 says:

jessica_ricci66:

If he walked away from a beautiful lady like you, he was not worth your time.
72 months ago (permalink)

frequent bear [deleted] says:

My first date as a woman was 4 months after my op . It was arranged by a friend who said he fancied me like mad and wanted to get to know me more so we met up first date was nice went for a few drinks had a nice kiss . Second time we went for a few drinks and a meal and he planned a night in a hotel which was amazing . We were lovers for 6 months but the romance fizzled out
70 months ago (permalink)

fast orange [deleted] says:

We meet 4 years ago we arranged he would come to my home I was so much I the closert Wow what have I done what do I wear it was my first time dressed with a man So dressed ready for bed white bady dolls and stockings held up,by my suspenders as I open the door he look delighted with me we have now professed to him buying me sexy things and taking me out for drives and walks in the country side we have such a nice time he still likes to see other cds and I have meet other men so life is good
30 months ago (permalink)

Debra Messer says:

My first date was a set up by my then wife. She had gotten me to a full time status and kept telling me that I needed to date men to fully understand and feel what being a woman was like. I had objected for a while but this night she slipped out of the place we were at with a guy leaving me no option but to spend the evening with the date she had set me up on.

It was nice and we stopped on the way back to my home and I guess between the drinks and being dressed and living as Debra for several months I gave into the whole evening. By the time we had gotten home I had sucked him off and swallowed for my first time.
30 months ago (permalink)

patriciastarria1231 says:

Hello sweetie that was a lovely story and im sorry that your girlfriend left and did not stay with you. It sounded like you treated her alright but alright sometimes is not good enough.
29 months ago (permalink)

lucky lumber [deleted] says:

My first experience with a man came after I started putting stuff on dating sites. I wasn't really sure about doing it at all but I enjoyed the flirting online without arranging a proper meet up to that point. Anyway, one day I cast caution to wind and invited (what turned out to be) a lovely middle-aged guy round to my place. I was obviously fully made-up etc and wearing seamed stockings, a black thong, a bra and a shiny coat! I was already used to working stilettos so I slipped on my sexiest pair and that was it. I was nervous but when I opened the door to him he looked delighted - although he was nervous too. He put money on the table, I fixed us drinks and we sat and chatted. Then we kissed, tongues furiously working. I suggested we went to bed and can recall walking ahead of him wiggling my butt as I moved. It felt divine! We got into the bedroom and he undressed. (I had removed the shiny coat at this point!). He was already erect and I started to lick his shaft graduating to his head before taking all of his cock in my mouth. I was wanking him and sucking him and with a great lunge he spurted all his juicy cum into my hungry mouth. I thought I may have gagged but I didn't. I swallowed it all and it tasted fab! I then carried on sucking him and he got hard again. I then took out a condom and rolled into onto his cock with my mouth. After a brief suck I then lubed my pussy and he gently slid himself in me. I can recall saying to him 'don't hurt me baby' and I also recall asking him whether he minded if I moaned! He made love to me - that's what it was; It was slow and gentle and I could feel him moving inside me. I started to work him with my tight ass and it got gently faster - if that makes sense. I was moaning and squealing like a bitch. I loved it. Then with a great lunge he let out a deep groan and shot his load inside me. We met several times after that but that was my first time. I then went on to escort for around 14 months or so. That gave me untold confidence. I enjoyed all of it so much that the only sex I can have now is with a man. In some ways, that could be seen as a shame but that's the way it is. It was a defining moment of being feminised I guess.
Thanks for reading and sorry if I've been too graphic! Lots of love xxxxx
28 months ago (permalink)