HomeMailOnline MembersSearchBrowseChatFriendsForum
 

My First Time Date with a Crossdresser

Interests:

Women Who Like Bi Men
i'd love to find another woman that is into having a bi man as her bf. I used to date this woman and we had tons of fun. Unfortunately she came to a decision that the lifestyle wasn't for her anymore. I really want to have a woman in my life that is into playing and having a great time
Indy Car
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
Asian Women
I developed a taste for Asian women while on a tour of Thailand. I had the occasion to date several that where between 4' 10" and 5' with very petite figures. All I can say is WOW. They where awesome women to be with.
Bukkake
Hi all
I live in york pa and i am a crossdresser. I have always loved watching girls on the internet getting drenched and covered in cum. I'd love to be covered in cum and have my mouth full of it from as many guys as possible.

Please msg me if interested
Outdoor Sex
I've always wanted to have sex outside, up the canyon. I fantasize about my date taking me up the canyon, making me take off all my cloths, him staying fully dressed, then taking his cock out and making me suck him until he's ready to fuck me good and hard.
Rape Role Play
I love the idea of being raped, I especially like the date rape idea. One of my biggiest fantasies is that my partner brings home a stranger (to me) and lets the stranger rape me while he watches, encouraging the stranger to be as rough as he likes.
Dildos
Say I Do to do what you's all can see me do in my Photo's with my Bace Ball , and it Feel Very Sweet to get to Ride on some thing that Big, But I Do Need (Help) with it From time to time, So if you are very interseted in Getting to Cum & Play in my PlayGround ? and you are a or do Say Hello some time ok? Bye - Oh Denizen PS, and I can take a Very Big Wet to as well as my Big Toy of a , bye...
All Male Threesomes
CCCUUMMM and FUCK Me Boy's 2 at a time or UP To 9 at a time ---> Just CCCuuMM and Get Off ON And wITH mE ? in philly pa ---> I do have a Place We can Meet and Get Off in C.C Philly pa, do say Hello back any time OK My sweet and Very Rock Hard Boy's ---> bye 4 now, Dennis.
Sex With School Friends
this is a School friend that i will love to see u's eat and get her all wet 4 me to taste her cum -- mmm yes she hot and she love to fuck and suck on you 2 or - she will do u all - 1 at a time or up 6 at a time -- very sweet she is -- mmmm yes do u look like her ? do send to me your nude pick's ok? i will love to see your very naked body's and i do hope that you do live in philly so we can all meet up some time soon in philly and i do know where we can all go and get very naked at - so do say hi ok? but bye 4 now Oh Denizen...
Squirting Females
I squirt from time to time and love to have it sucked up and be licked clean. Shiver..
Triple Penetration
I Want Your 's To Cum 4 Me - Yes Do Take a Look at My 10 Photo's and If You Are Interested and Want To Have a With Me - Just Go To My Profile and Say Hello Some Time and Let's Meet Off Line and In C. C. Philly PA Some time Real Soon - But Bye 4 Now - Dennis...
Astronomy
We love Parties, even host them from time to time.

Be Happy T & D
Truckers
I am looking for bisexural men in the wisconsin....looking for getting together from time to time...must be clean...
if interested look me up
Quickies
WE All Have To Settle For A Quickie From Time To Time & Hey There's Nothing Wrong With That....... Get It Anyway YOU Can Get It, Anytime YOU Can Get It ->->->
Men Licking Pussy While She Is Getting Fucked
Was with a couple I knew and played with from time to time and she told me she had seen something in a porn movie she wanted to try. Her hubby sat on the couch as she staddled him and I knelt between their legs licking her. Every so often he would slip out and I would take him in my mouth and look up at her before helping him back in her pussy. It seemed to drive her even wilder watching me bob up and down on him before helping him back in her and going back to flicking her clit with my tongue. . She was screaming by the time we were done. Doing that became a regular thing for us whenever we would meet. I got transferred and we lost touch. Wish I could find another couple near me that would want to do this.
Men Eating There Own Cum
I did it for a GF of mine one time and she went wild. She didn't know I was bi at the time and asked me if I would like to do it for a friend of hers and I said I would if I could fuck her. I fucked her and she wanted me to eat my creampie out of her while her GF ate her wow love to meet some couples for MMF fun. Any offers in Greensburg PA?
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

Profiles:

I am filling this out for the first time so please excuse the short description. I'm am a bisexual married discreet male to female crossdresser who enjoys giving oral sex. If you're in my area please write to me.
Single, attractive, super clean and very selective business proffesional. Divorced for years, grown children. Part time crossdresser for rmost of my life. Looking for similar as a regular playtime partner. If your not into dressing, no worries. Mostly interested in oral, JO, and safe play.
Bi female and straight man.We are not looking for a super-model and don't expect anything other than you letting an upscale white couple take you out on a date and show you a good time. No strings and no drama...just hanging out, maybe a few drinks (420 is OK too!) and getting to know each other. We can have fun chatting and call it a night or we can move on from there and keep going all night! Now for the part I hate to have to say so bluntly but NO MEN - NO means NO - NO MEN...no couples and no, your bf/husband/brother/priest can not watch and definitely NO you are not the one guy I will say yes to...save yourself the trouble.
I am a very complete part time crossdresser. I'm looking for the right person to love all of me. I love women but men love me. So its hard to deny a good time!lol. I am a manly guy(aside from my alter egeo lol). I am very healthy, I am in no way a sissy when dressed as a man. lol I am a very sweet, honest man. I work hard and live a very normal life. I'm very active with many sports and love the great outdoors. My life is not centered around cd/tv play. It is just a part of me that will always be there. Finding the right woman to fit me in and out of the bedroom has proven to be impossible so far. I have no problems getting the girls but can never find one that would be into my bi side or have one of her own. When I do... I could never bring them home to mom lol. I need a lady in the street and a freak in the bed! I hope to atleast make some friends that know that this is apart of me.
crossdresser and ver curious to explore
I am a submissive crossdresser who is looking for a mistress to train me to be a better sissy. Have a nice day.
A Bi-Curious man that has an urge to share it with others Bi or Bi-curious males. My only encounter was with another man and just a 69 that my wife set up as a MMF date. We have had a MFF also to that wasn't that exciting for neither of us, more on the lack of participation form the other. So now I am looking and would like to meet another Bi or Bi-curious male and continue to fill my desires.
Hi, If pressed for a label, I would define myself as culturally straight, bi-sensual, bi-sexual, emotionally-bi, kinky, poly male who has dated both men & women with his wife. Though we are very happy together, (18 years) she and I now also date separately. Though open to many experiences, I also respect all boundaries & go at the speed of the slowest participant which, more often than not, may be me.
I am a very much closeted bi guy. I have had some but just want to play and explore more safe, sane fun. I have, black hair blue eyes, educated, sincere and very entertaining (yeah fun!). I am looking for fun and sexploration. I have had some experience and VERY open. Some stats are: 5'11" and told that I am quite cute (by men and women). . -- Bisexuality immediately doubles your chances for a date on Saturday night. -- Woody Allen
Well I have come to terms with who I am and what I want out of life. But it seems really tough putting into words. I am bisexual and have been for as long as I can remember and I am a crossdresser. The crossdressing is something fairly new. I had messed around with it a little over the years but now I am embrassing it to the fullest. That doesn't mean I dress daily or even weekly(maybe one of these days) but when I do it's all out. I have never had sex while dressed but I would like to one of these days.
We are a married couple just looking for a little fun from time to time. We will try almost anything at least once. We are not into BDSM or SCAT. We are both willing to play on the side from time to time. As long as we are both comfortable with the situation. If your interested send us a msg.
I'm a nasty crossdresser who loves nothing better than being on my knees and servicing groups of guys for bukkake facials. I videotape myself sucking dick and wearing cum, have lots of pics for you. Besides groupsex, I'm interested in sucking off guys in public. Occasionally enjoy women, as long as they enjoy my dressing.
51, tall 6'6", athletic build 235lbs, blonde hair, clean shaven face and cock, tattoos, pierced cock. I enjoy secure people, people who know how to have fun. Other than poo, kids, and animals I enjoy about anything sexually. I love pleasing partners not only with my body but also with my mind. I can be submissive or dominant, top or bottom. I enjoy using my hands, fingers, tongue, cock and ass to please my partners. I can be happy with a one on one date or in an orgy.
We are open minded,cpl have no hang ups of anykind. (NO UNDER AGE) We love anything and everything. s with all men, s with a women and a man. I am Bi have been all my life, I find it to be a wonderful way of life. I am very experienced, I have been in this life style over 35 years.We have a better then good idea of how and why to please men or women. Not Looking for more then just new friends at this time. But we can always rethink that from time to time if the time is right. Out for now but not dead.
I am a 39 bimale crossdresser. I am 5'4", 125 lbs., and 28" waist. I am smooth all over and dress all out, (wig, makeup, earrings, bra, panties, stockings, short skirts or dresses, and heels. I am looking for a regular (women with strap-ons, tops, or a couple). I am a bottom only with guys, sorry. I am very fun, out going, safe, ddf, sane, and discrete. With guys I am into kissing, making out, j/o, oral, anal ( LOVE to BOTTOM). With women I am into, kissing, making out, oral, bottoming for a strap-on, and vaginal sex. I am a little submissive but not into bdsm, rough play, piss, scat, or anything else sick.
In-shape, nice looking, professional, married male looking for a nice couple to hook up with from time to time when schedules allow.
I guess you would say I am actually a gay still in the closet. I love man to man sex and all it entails. ROugh slow fast smooth, soft hard, I love it all Just about anything goes with me from mild to wild depends on what my partner wants at the time. Something I would like to do is take on about 4 men at one time.

Forums:

wanted women who likes to dominate men crossdresser and fuck the crossdresser with a strap on
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.
looking for some first time fun. i am a crossdresser
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
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
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.
Hi, im a 19 yr old crossdresser in suffolk county. Im looking for other cds, girls and maybe guys to get together with to hookup. Im into anything really. Im passable, i go out a lot and i hook up often. I dont have female pics , cuz the only time i dress fully is when i go out or when i meet people, and i never have time to take good pics . i have my male pics in my profile and if you want more just ask. If your interested, email me at ... i prefer a pic guy or girl pic. any age.. write me!

mwahz
Hi, I'm a 48 year old crossdresser... never been with a "real" man, but looking for some cam time, maybe more. please write or IM me..
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. ual 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!!!!!
Im curious if it would be possible to make the original post date alittle larger or the date on all posts. I occassionally go to respond to one and forget to look at the date only to find out later the post has been there a year. I understand keeping some of them up since it can start a new bunch of replies sometimes but I have read many responses today that tell the original poster they want to get together only to also look and see the original request is months old.
Just an idea.
Tricia

Testimonials

deepthroatswallower
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

Related Searches



Did you know?
Pop-Up Blockers
Did you know that Pop-Up Blockers can prevent you from being able to send e-mails, chat, and even send and receive instant messages? If you have a Pop-Up Blocker, Make Sure it is set to Allow Pop-Ups on bisexualplayground.com! There are no advertisements on this website.
Click Here For Assistance
Disclaimer: Individuals appearing on this site have contractually represented to us that they are 18 years of age or older.