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My First Time Date with a Crossdresser

Curious guy looking for a shemale or crossdresser to meet here and there. No strings. Lookin for a good time. Wanted this for long time now so here i go. Lol. 5'9 160 lbs. clean. Disease-free. Want to stay that way. Love sports. Like to watch a movie and just lay there and cuddle and play. Funny. Do not look my age. Told good lookin. Never been wit a shemale or crossdresser or another man. Looks arent everything. But nice legs and smile and teeth and eyes get me good.
this is more for him, he wants to have a male experience. So we thought we could have a first time couple ``date``.
long time crossdresser who is not passable
Closet crossdresser looking for my first time, easy going laid back guy . I am mainly a bottom looking for a nice patient top.
print favorite this post Hot phone fantasies bi lover -friend (Fort Wayne) hide this posting body : average height : 5'11" (180cm) status : married age: 50 Only Bisexuals that loves phone sex no exceptions! if it s not for you fine just go ... I am very happy watching a hot porno and dreaming of the lover I need.. NO email Tag I do not keep nude pics of my self on the computer.... I will send a face pic ..... I would love to meet and have you take some pics of us .... I need some one with the same needs .. The reason is first it is hard to get picks with a cock in one hand lol . And the wife might find them and she has ... the good thing was she liked it ..... No email tag just one with your picture and phone number it is that simple! after you read this you either you like role play and want to set up a play date or you do not so read and respond Only if this is you! I need my lover my boy friend my play mate my lover. Phone Sex Fantasy Friend & Lover No exceptions: Must have phone number and a recent Pic. This is a must..... or simply do not reply..... I need a lover that has no problem with phone sex in-fact loves pleasing one another. I can only talk to set up a play date week days from 9 AM to 2 PM Monday - Thursday.... I do not Text at all. ((Just not into Texting or endless e-mails So ...... In first e-mail enclose phone number Picture and best time to call so we can set up a play-date.....)) I am sick of time wasters! . The one's that just can not read my add. It is that simple either you have a picture and a phone number or please do not answer my add. I enjoy hot phone fun. So pull out your cock put on a hot porno and tell me you like to dress like my sister or dress like my maid, Kiss me like my boyfriend. I need a sex partner one the loves what I love. One that loves roll play Daddy needs that one special man that loves to suck cock & make out like wet teenagers Kiss me like my wife dose. . ... Open up relax and feel free to cum like lovers. I need a Bi boyfriend that is wild in bed that loves hot phone sex but down to earth out the bedroom some one that can be a true friend one that can be counted on as a friend. There are so many fantasies to share. . .. I just need that one special lover. . . I am looking for that one but I hope there will be more than one reply so I will get back with those that make me hard with a hot e-mail with that number and a face pic, If any of this add is not for you simply do not waste my time. . .. And if it is . . ... I need you. . ... to need me bring out the soft yet wild passion Let's set up a play date., I am married 50 white 5' 11" blue eyes brown salt and pepper hair 6 1/2 inch cock
Very sexy crossdresser loves leather skirts fishnet stockings in 6 inch high heels sexy crossdresser in his stockings and 6 inch heels
Hi all im asian crossdresser .im tall medium build black hair n black eyes.short timmed hair.ive been dressing for long time....
Fun outgoing guy with an athletic build looking for a date with a tranny.
Iam a submisive man iknown this for many year but to date the practice of submisssion has been limited i have a strong desire for 24/7 the limits would be few
Bi crossdresser here looking for fun
Crossdresser
Crossdresser up for anything
Crossdresser
bi crossdresser
sexy crossdresser
I am looking for another crossdresser for gurl fun.
47 year old crossdresser
I like a crossdresser, I went out with a crossdresser, and I didn't know at the time, so when started to play and I was surprise
im a crossdresser interested in meeti.g a good looking .tuff body black man w/ bbc... maybe... mayne set up date to go dancing and maybe more...
wanted women who likes to dominate men crossdresser and fuck the crossdresser with a strap on:):-PKiss
Delilah, rather lofty expectations for a first date, although could be a consideration I suppose - what happens between the first hello and the actual date. Before I take any date to one of my fav places, I better have some sense that the date has a real interest in me, rather than the dipping (in this case the wallet). Unless there is some mutual attraction, the approach you outlined sounds more like materialism than establishing a relationship.
up date on Jack and Jill Masturbation get together....
where: Woodland Hills,CA
date: 11/13/05
Time: 4:00 pm

Lets all get together on this.. would like more couples or ladies to join
and when you do set a date - oh do let me know back - on what the date is and where it is and the time 2 be there o.k. ? and i will love 2 see u's all there 2 as well - bye 4 now - Dennis.
If you run into your peers at a swing club or bi club that should tell you a bit more about your peers too. They dont let just anyone in most swing clubs and if you arent bi or looking for someone who is bi why would you be in a bi club?? They are probably there for the same reasons you are so Im sure they would want the same discreetness.
Do you ask all the straight women you date if they are bi? Do you do this on a first date basis? I dont tell the men I date right away that I am.(Not the ones I meet locally anyhow) Thats something that comes with getting to know each other better. Thats not first date conversation. Generally only the men I meet online are aware of my sexual preferences/choices.
Also as Nessa said it takes patience to meet anyone online, regardless of sexuality or gender. Take your time, dont be in a rush. Whats that old saying...when you least expect it.....
mmmm, I agree with havnnnfun and hopefully i can be counted in on this group. I'd even volunteer my body to be initiated (1st time) if it hasn't already been done so by the time the group gets together.

Also, think about the limitations, like how big you'd like the group to get. Or if it gets a considerable size, their can maybe be 2 meetings. Where maybe half the group mite not be able to make it a certain date but can make it on another date.

PEACE
looking for some first time fun. i am a crossdresser
I am in the process of planning an all girl get down at a hotel in Birmingham, AL. Ladies, please email me via this site to let me know if you're interested. Although, I would like to host the party in November, I have not finalized a date. In your response to me, please let me know which date(s) would be best for you. The final date will be decided upon based on your responses. I look forward to hearing from you all soon...mochaBrown~
much like Oman, I started when I was very young with a friend, we were 11. Then nothing til I was about 21 and married when I got into a situation with a younger pubescent cousin(male of course) and I gave him his first blow job. More time elapsed and I was 28 divorced for a second time and went on a date with a gay man, unfortunately we turned out to both be "bottoms" so things didn't work past the one date, but I had fun sucking him while it lasted. Since then I have had several one time hook ups with other married guys but haven't found the one guy to become friends with and have regular hook ups, until now I hope. My wife knows about me being bi but wants nothing to do with it or even know when I hook up, so she would never ask me to suck someone. I do have her permission to do so on my own, just so I am very discreet, and she or her friends don't find out so she gets embarrassed.
Date/Time/Place? Sounds like a great time! Looking to explore for the first time. Patience is a virtue...as is exploration. I'm down with it all if there's some time to acclimate.
Crossdresser looking for a m-f Couple that would like to enjoy a fun time. A little shy at the start but very open to all most any thing. ( no PAIN)
hey im a crossdresser from devils Lake. wanna meetsome time we could dress up together. who knows. maybee even have some fun.
Hi, I am a bi crossdresser looking to have some fun and excitement with a couple, man, woman or another cd. Get ahold of me lets set the wheels in motion for a very fun time
Hi I'm Cindy a crossdresser,,I read the posts here,,,and guys don't give up, there are alot of xdressers around..I for one...I'm into Black men but I will make love to a white guy,,but I prefure a Black stud..I'm a white crossdresser 5'5 Tall ,got a soft white ass for my man..Look at my profile and maybe we can hook up at a motel..Hope to hear from you all Black studs..
Love,
CindyKiss
It is damn hard, I've been looking for a long time too. A lot of women are curious or more, they just won't admit it until they know the guy enough to feel comfortable and that takes time. They need to know they can trust the guy, before bringing another fem into the picture and not threaten the realtionship she has established. Sexual pleasure adventures should enhance the relationship, not threaten it, but most people due to social upbringing cannot deal with it. Since you are still young (haha), perhaps another approach.... date some of the women, after a couple of hot steamy session, just ask if there is interest, you might be quite surprised? Look for clues, if the date already has a bare pussy..... most straight women I know don't go that far till I do it for them hehehehehe 95% of the women that I know that are bi, shave, they don't like curly dental floss any more that the guys do!!!!!

Interests:

Guys Who Eat Cum
Cum in a little film photo container and freeze it after each time you cum. You can fill it up with about 7-10 loads and then let the big cumcicle melt in your mouth at some later date! WOW!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!! Glob by glob swallowed... sexy, sexy, sexy hot! A great way to taste yourself for over 10 to 15 minutes or so!
Indy Car
Love Indy Car
On this date in the final race of the season a horrific accident occured at Las Vegas Motor Speedway on lap 13 claiming 16 of the 34 cars in the race.
It also claimed the life of 33 years young 2 time champ Dan Wheldon.
Godspeed Dan Wheldon!! RIP
Crossdresser Male To Female
Hi guys girls sexy crossdresser here
Hotwife
Oh yeah i love hvin a hot wife
Helping her dress up for her date
Her telling me how big his cock is
Then when she gets home with her pussy full of his cum
She mks me eat her out as she tell me how good he fucked her
How her sucked all over her big tits and left his marks all over them
Mmmm im sooo lucky to hv a hot wife 😍
2 Girls 1 Guy
We are a happy married (25 yrs) good looking couple looking for a bisexual, drama free, kinky woman to pleasure me and to show me a few things that pleasure her. I'm 43 and very curious and he just wants me to fulfill my fantasy of a sexual experience with a woman. This would be my first time and he wouldn't get involved. He just wants to watch as I get my pussy and tits licked and sucked until I come. I'm more of a submissive type so if you're interested, please message us! *we are not looking for a commitment or long term relationship but if all goes well, we can continue this from time to time.
Sailing
When I owned a 22 footer we always sailed....started out each trip with women taking off their tops ( only two at a time), but would get them naked after a short time. Ferries to St. John and Tortola got a great view.....
Couples Searching For Bi Males
I would like to find bi couple that is love caring. That like to have a bi man to have fun and spend time. I like outdoors,coockingand spend time with pepole and making them happy Hug:-P
69 With Another Man While Getting Fucked
Its been a long time since I had tow men at the same time. Both men fucking me hard. Both my holes filled with hard Cock. Both Cocks shooting fresh hot Cum. I used to do this all night, 4 or 5 times a week. I really miss this. Lindawantabe
2 Cocks In 1 Ass
Seattle area - As a couple Michael loves BIG things up his ass and can take two 2" diameter dildos up his ass at the same time. Now we just need to find two well hung bi guys to come fuck his ass at the same time!!! Of course we'd also take any really hung guys or girls that like to fuck guys with strap-ons or their fist!! Patricia will be there helping and taking 'em too!
Gay Incest
I spent 2 summers dureing high school in Texas with my uncle and his 3rd wife. I don't know how he knew that I had b egun exploring bi... I had a serious girlfriend by that time etc, but he did know and during the 3rd or 4th week he came on to me. It started with mutual oral only for the first couple of weeks. He was a larger guy, slightly bearish, handsome and rugged and very well hung. I was always a little scared but secretly really into it. He took my anal cherrya little over a month after i had been there.... god it was incredible.

I took so much cum the rest of that summer and all of the next i was hooked! His wife loved it too so was a very cool time 30 years ago...
Bisexual Men Giving Oral
I love to suck on all cock. I don't care how or how small. I have like have them in my mouth. Going deep in my throat having it cum your mouth. I was about 10 when I found out that I like sucking. I was coming home from school and met a guy about and we talk for a time he took he's cock out and show it to me ask if I would put it in my mouth for hem. I did and he started to push in deeper and deeper until he had it all in my throat I know that I like it!!! So I seen for long time. So if any one wants get suck in mid Missouri
All Male Anal
I was around 18 when I was forced to have sex with two men. That was the first time that I sucked a dick and was fucked in my sissy white ass. That first night I hated it. In the morning they told me I was going to be their sissy bitch 4, 5 maybe 6 times a week for as long as they wanted. Each time I liked them using me more and more. It got o the point where I could hardly wait to see them again. You know I must have liked it. I'm 70 and now looking for BBC. I want to say that I deep throated 13 inches of BBC. That my sissy white ass took every inch of the 13 inches. That my white ass is still holding Black Seed. That I love the taste of Black Seed. Lindawantabe
3 Girls 1 Guy
The last house party we attended, we ended up with 4 other bi guys ands had an absolute blast. We both sucked every dick, one and two at a time. I got fucked really good and a 5th guy joined as we were all beating climax and all 5 shot their loads on Khela's tits and neck. I slopped up a handful of their mixed cum and while I was using that as lube to jack out my load, buried my face in the mess on her tits. It was the most cum I have ever experienced at one time. Needless to say, I orgasmed exquisitely and shot my load all over her face and tits as well. Naturally, we showered together afterward.
M-M-F Threesome
Which story should I tell? I'm going to tell the one that I still think about to this day. This happened in 2006, so it's been 11 years, but I remember it like it was yesterday. When in California I was hanging out with a woman who turned out to be a "crack Ho". And I do mean "Ho". We got ourselves a motel room that we paid week-to-week. She would sell it to pay for the room, and it was also next to our connection. It just happens that on a Friday night there was a book selling club from Georgia that checked in with at least 40 guys trying to sell books. Being from Georgia, 30 of the 40 guys were black men. She approached one of them and said, if your interested in purchasing some "crack" I'm your go to girl. It didn't take long before the door was getting knocked on. Within an hour she had probably sold over $2000.00. Apparently, she made some promises she had to cover also that I didn't know about until it happened right before my eyes. Out of nowhere she just unzipped his pants and out popped the biggest, thickest, black dick I have ever seen, even in porn. On top of that, comes another knock on the door. I answered the door and another guy was looking to buy some, not knowing what he interrupted. She sold him what he wanted, and I saw the look in her eye, she was set on fucking them both. Next thing I know, she had them both naked and giving a double blow job! That was hot to watch. Servicing 2 BBC at once was so hot to watch. Especially when they shot their loads. Next day I got my chance to do what I wanted. She had an appointment for a few hours, so I was alone. Minutes later was a knock on the door, it was the same guy looking to buy more. I said she was gone but I could get some for him. I returned with his $80.00 worth and smoked with me as a thank you. Finally, he asked me if I was o.k. with them fucking my old lady? She was a "FWB" type relashionship. I told him I got into watching them especially when she was sucking both deep throating. A few more hits and I got the balls to ask him if I could suck him off, and of course, I met him any chance I could before the road show packed it in. She never did know about the fact that him and i hooked-up. Would love to do that one again. My only Blackman to date but I would do anything to meet up with another black guy. Someday!!!
Men That Want To Be Fucked In The Ass
I was 15 when I first got my ass fucked it was by a 70yr.old man that ask me if I wanted to make some money said yes doing what he told me what he wanted to do to me I walk away from him and gave it some thought turn around an said he took me to his room hugged play with my ass a little then pull my pants off them he pull his off it was the first time I seen someone else cock he rubbed it against me and play with my cock then he stuck his cock in me it hurt at first them felt good then I felt him shoot cum in my ass I love it we met like this along time then he had me start sucking cock and cum in my mouth I new then I was hook on getting fucked and sucking cock HugKiss
Cock Sucking With A Transgender
I once picked up a transexual,but didn`t know it at the time. She was so passable, but when I found out she had a cock it didn`t matter. I love both cock and pussy. She was such a knock out for a black gurl. We got to her place and she took off her top to expose the most sensual tits. She notice me looking at her crotch and told me she was a he or use to be. She then took off her shorts and there was the best looking black cock I ever saw. I gave her a good blow job until she let loose in my mouth, It was like being in heaven. I swallowed every drop of her juice. She then returned the favor. I didn1t last long because when I saw those lips wrap arouond my cock I was still reeling from me giving the same treatment to her. That was such a good time. Love you transexuals. Hug
Women Who Like Bi Men
I'm a bi male I like sucking cock and getting topped 7 I LOVE eating pussy would love to find a woman that let me lick her clit while her husband are boyfriend fuck her and broth cum in my at the same time that happen to me a long time ago we where like in 69 position she on her knees sitting on my face and he came up behind her dogging style and started fucking her I could feel his balls on my fore head while I was licking her clit she started moaning more and so did he when he cummed in her pussy it ran right down in my mouth he pull out and stuck his cock in my mouth I got her cum and his too and never find anyone to do that with again I love it so if any women out would to do this drop a line.HugKiss

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Maybe I'll be able to write another compliment. Within 24 hours I had found and made a date for a meeting with an almost perfect play partner. Will know in 24 more hours if I can write a success story. I do find the site easy to navigate. One of the better sites I have ever used (including business sites). Jay