I have been chatting with another "Gurly"....Penny.....who lives in Dunedin, for quite some time. During the times we have been chatting, I found that both Penny and I had many things in common. One of the things we found that we both knew another "Gurly"....Claire. Claire lives locally to me, and we frequently get together for dress-up sessions, which invariably lead to "Panty Play"
One time when we were chatting, Penny told me thst she would be coming up to Christchurch to do some work, and would really love the chance to meet up, face to face. I mentioned this to Claire, who has suggested that Penny would be most welcome to spend a couple of nights at her place, and I would be more than welcome to stay as well.
I am really looking forward to this opportunity of having a lot of sexy fun with two other "Gurlies" ........and will write about the experiences !!
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What are your experiences?
Discussion started by Rikki , on Tuesday, 15 September 2009 13:39
My first was many years ago with a man I met online. We hooked up in a hotel room.
It was pretty hot! It was there that I learned that I like to top.
He was very excited and I had to calm him down and slow him down and her like being told what to do and I liked telling him how to please me.
It ended with me jerking off and coming into his mouth.
The next experience was with a couple...a crossdresser and his girlfriend.
I'll write more about that as soon as other start writing their stories.
What's great is that there are many crossdressers that would like to try ot woth others and now, after reading the discussions they will have some ideas on what it might be like for them.
It was pretty hot! It was there that I learned that I like to top.
He was very excited and I had to calm him down and slow him down and her like being told what to do and I liked telling him how to please me.
It ended with me jerking off and coming into his mouth.
The next experience was with a couple...a crossdresser and his girlfriend.
I'll write more about that as soon as other start writing their stories.
What's great is that there are many crossdressers that would like to try ot woth others and now, after reading the discussions they will have some ideas on what it might be like for them.
Latest Discussion
My first experience was with a TV in the North East, we had chatted online and arranged to meet at her house. I got there early and she was not quite ready and watching her get ready and transforming into a women was such a turn on. She could see that I was so aroused and gently run her hand down the front of my jeans laughing, I nearly blew right there and then. We went and sat down in her sitting room and chatted over a glass of wine by this time my jeans had a damp spot on the front, my stomach was in knots I tell you. The talk turned sexual and about breasts she asked me if I'd like to see hers and obviousley i said yes. she stood up and undid the dress she was wearing and slowly lifted the bra up over her nipple, I asked her if I could touch and she told me to feel free. At that point everything changed, I gently pinched her nipples squeezing the breast she obviously like this I lowered my head and took her nipple in my mouth (I could taste her perfume) she whispered for me to bite the nipples, I did and she let out a loud groan. By this time i was in bits my hands were going everywhere I lowered my hand to her knee's and explored under the dress, she was rock hard and as wet as me, this was my turn to groan. I moved behind her and was pinching her breasts with one hand and slowly masterbating her with the other, my lips were gently biting her neck, my cock was nuzzled between her butt cheeks, I told her to turn around and I pushed the dress to the floor as she did, she had on white hold ups and white panties, I dropped to my knees and blew on the panty covered clit, I slowly moved the panties to one side and and removed what was a thick clit, the foreskin was peeled right back and the head pulsing at this point I looked up and saw her face her eyes were shut whilst looking at her she gently put her hand on my head and pushed it gently forward, I took her clit deep in my wet mouth, she moaned hard as I moved up and down over her, I knew that this was what I had wanted for so long, her knees had bent slightly and her hips were pushing forward she put both her hands on my shoulders and started to push a little harder at this stage I was in wonderland my hand was stroking my cock and she was basically fucking my mouth she started to gasp then all of a sudden my mouth was full of a thick hot liquid, I didn't swallow I let it fall into my hand and started stroking myself with her cum, she finished shaking and gasping and told me to stand up and at that point she took my cock covered in her cum into her mouth and gave me the best oral sex I had ever had within seconds I was shooting jet after jet into her mouth she couldn't take it all and it was running out of her mouth down my cock and balls. That was my first proper sexual experience with a TV/TS, we both came again that night and we both had a fabulous time............no anal sex was involved just oral which was fine by me.
244 days ago
I met him at his home. He was constantly worried and nervous that a family member would return home and catch him in sex with me. He was dressed in a short black sheer nightie. I changed into some women underwear, my hose, and heels. He at in a chair. I sat in front of him and sucked his cock. He was uncut and did ot want his foreskin turned over with my tongue, but otherwise he began moaning and enjoying me sucking him. He grew hard and eventually did cum in my mouth. I enjoyed taking his cum and continued sucklng and swallowing his as he came. That was what he wanted - sucked off while he was dressed in women's lingerie that excites him. Maybe his wife's nightie - I do not know. He did not offer to nor sucked me. Oh well. I washed the rest of his globby cum down with a few siips of Pepsi, dressed, and left his house. Never saw nor heard from him again. I wanted to jerk off in women's clothes with somebody similar as him, but was afraid his family wouild catch him at it. I enjoyed it and would do it again.
286 days ago
Since my previous experience mentioned below, I have been dresed and made up for sex with some other TV/CD's, and must admit to lift a skirt to find stocking tops, suspenders and a wet stained bulge in shear nylon knickers is such a turn on, and I just have to drop to my knees and work on that bulge with my mouth ... still waiting for the right girl to have her erupt into my mouth though
556 days ago
I went to an afternoon TV party a few years ago and dressed up as a filthy skoolie slag and was made up by the owner ( a real woman)
I teetered into one of the many rooms sat down making sure my knickered bulge was on show and was joined by 4 TVs who sat next to me
One sat very close and started chatting as her hands wandered up my legs, then up my excuse for a skirt and as I opened my legs wide her hand went into my knickers
I just sat ther sucking on my lolipop as she worked away into my bulging knickers stroking my rampant clitty
By nnow we had an audience and I felt another hand up my other leg and a few TVs stood infornt of us skirts hitched high as they stoked their own knicker bulges
Then with no notice I shot my load all over my black shear seamed stockings and into my knickers
I was then taken into another room and had by 3 TVs while a eager rampant admirer sorted himself out over me
I teetered into one of the many rooms sat down making sure my knickered bulge was on show and was joined by 4 TVs who sat next to me
One sat very close and started chatting as her hands wandered up my legs, then up my excuse for a skirt and as I opened my legs wide her hand went into my knickers
I just sat ther sucking on my lolipop as she worked away into my bulging knickers stroking my rampant clitty
By nnow we had an audience and I felt another hand up my other leg and a few TVs stood infornt of us skirts hitched high as they stoked their own knicker bulges
Then with no notice I shot my load all over my black shear seamed stockings and into my knickers
I was then taken into another room and had by 3 TVs while a eager rampant admirer sorted himself out over me
560 days ago
My first time was with a friend of mine who was married as am I. We CD and socialized a lot together and my wife knows and approves me dressing. One evening after my wife went to bed he went down on me. This he started to do often. One evening I asked him to make me suck him. He did and I was hooked. i then would serve him each and every time he came to my house. We have lost touch but i have met with several CD's since and just love to serve them and swallow all their yummy cummy.
572 days ago
This happened several years ago. We'd met on line and chatted for about 6 months before meeting for the first time. I have to say I was very nervous about our meeting but still went thru with it and was very glad I did. We met in a local motel and went out for lunch. We then went to a local park to take some pictures. I believe that while I was taking them, she was toying with me and teasing me, showing lots of leg and such. Will continue this later!!
592 days ago
i love to be sissy with another cd. I have a new gf that thinks alot like me. We have been meeting in Dallas and getting a Hotel and playing. She and I adore being sissy gurls together. We both like the teen girlly look and love lots skirts short and cutie tops. Now neither of us can pass but we really dont care. We usually dress and go to the green lawn area of dallas with no problem. Last time i wore some blue polka dot capris and a cutie white top that exposed my bra straps. Of course I had on my pink A cup bra and panties. I work makeup, short brown wig, pink lipstick, pink toe and fingernail polish, white strappy sandals with my toes exposed, hooped ear rings and a cutie little purse. My gf wore pink bra and panties, tight white girls shorts, cutie pink top, blond wig with red lipstick, red nail polish, white strappy sandals, and cute purse. We felt so sissy leaving the hotel room and got a few stares but all ok. We bought each other matching bras and panties at this one store, and held other things up to each other and said how cute it would look on us. It was so fun. Then we ate and kinda got hit on by a cute guy. But then went to hotel room to play. We are so sissy together. We dressed each other in lingerie as we sipped our wine and prissed around the room for each other. We slow danced and kissed deep kisses. We played with each others clitties and licked and sucked so much. We went to bed and continued sucking and fucking and took each others cum in our mouths. Next mornig we ordered room service and answered the door in our lingerie. It was so fun. When we left we kissed publicly in the parking lot. xoxo Stephanie
595 days ago
I have not yet had the experience, but reading all these experiences, I am so ready.
619 days ago
I have had sex with five other crossdressers I met online and all were married and needed to
express their fem side. Had some mutual nylon panty masturbation and also oral sex which was great.
I have even pulled down panties for two and given them a little spanking which they loved.
express their fem side. Had some mutual nylon panty masturbation and also oral sex which was great.
I have even pulled down panties for two and given them a little spanking which they loved.
663 days ago
T too met a cd online and seeing as both our wives were going to be out of town we decided to get together. When I arrived at his house, he was already dressed and on the phone. I carried my suitcase full of lingerie in and started dressing while he finished his call. Then with both of us dressed he took me into his bedroom and showed me his wifes and his toys including a strap on that she used on him. He also showed me her panties and lingerie. We finally layed down on the bed and after some preliminaries he started sucking my cock and continued until i came in his mouth. Then it was my turn. His cock was BIG and all i could do to take it all in my mouth. I sucked and sucked on his cock. I continued sucking for quite some time, but he couldn't cum. So we took a break, he smoked a cigarette and then we went back into the bedroom and I started sucking again. This time he was finally able to cum and shot a big load down my throat. It was wonderful and tasted devine. Think that was the first time swallowing for me. I loved it, unfortunately that was the only time for the two of us.
666 days ago
I HAVE DONE IT WITH ANOTHER CROSSDRESSER,AND I WAS NERVOUS THE 1st TIME FOR ABOUT 10 MIN. THEN I KNEW WHAT I WANTED AND ALWAYS WANTED TO DO WITH ANOTHER MAN IN PANTIES. IT WAS GREAT AND A LOT OF FUN. I ALWAYS WANTED TO SUCK ANOTHER MAN'S DICK. I DID IT,IT WAS BETTER THAN I EVER EXPECTED.I WILL DO IT AGAIN WITH ANOTHER MAN WHEN I FEEL SAFE.
814 days ago
My first experience with another crossdresser started in an online group; we started emailing each other and finally decided to meet. The moderator of this group (alas, since moved and no more) would let her apartment be used for get-togethers.
I arrived to find my date all decked out in black corset, hose, panties, and bra, topped with a mane of red hair. I soon changed and joined her on the sofa. We chatted, toying with each others' thigh and soon wound up kissing and running our hands over each others' panty covered cocks. We soon were kissing and grinding against each other; I loved how she grabbed my asscheeks and spread them, then pushed them together, massaging my asspussy. We took turns sucking each other, then I sat her back on the sofa and straddled her, sliding my asspussy down onto her hard cock. I took it slowly, letting my asspussy get used to it, then slid down more until I bottom out. From there, I bounced while she fucked me.
She soon had me kneel over the sofa and entered me from behind. It was wonderful to feel her hands pulling on my hips. I especially love dirty talk and the more she talked dirty, the dirtier I talked back and the harder she pounded me. It was wonderful and all's I could think was "Why hadn't I gotten dressed and fucked like this before?"
She laid me on the floor on my back, lifted my legs and slid her cock in and started thrusting. My eyes were closed and I suddenly felt a hand slide under my bra cup and start tweaking my nipple. I opened my eyes to find the apartment owner (a gg by the way), enjoying herself. She asked if she could take pictures and we agreed. Perhaps I'll post those precious memories at some time.
My date soon reached that point where she could hold back no longer and pounded away until she came. We were playing safe but I do so wish I could have felt her cum shoot into me. She pulled out and I removed her rubber and licked her cock clean, then shared it with her in a cum-smeared kiss. It was heaven.
She wasn't finished however.... but I'll save that for another post.
I arrived to find my date all decked out in black corset, hose, panties, and bra, topped with a mane of red hair. I soon changed and joined her on the sofa. We chatted, toying with each others' thigh and soon wound up kissing and running our hands over each others' panty covered cocks. We soon were kissing and grinding against each other; I loved how she grabbed my asscheeks and spread them, then pushed them together, massaging my asspussy. We took turns sucking each other, then I sat her back on the sofa and straddled her, sliding my asspussy down onto her hard cock. I took it slowly, letting my asspussy get used to it, then slid down more until I bottom out. From there, I bounced while she fucked me.
She soon had me kneel over the sofa and entered me from behind. It was wonderful to feel her hands pulling on my hips. I especially love dirty talk and the more she talked dirty, the dirtier I talked back and the harder she pounded me. It was wonderful and all's I could think was "Why hadn't I gotten dressed and fucked like this before?"
She laid me on the floor on my back, lifted my legs and slid her cock in and started thrusting. My eyes were closed and I suddenly felt a hand slide under my bra cup and start tweaking my nipple. I opened my eyes to find the apartment owner (a gg by the way), enjoying herself. She asked if she could take pictures and we agreed. Perhaps I'll post those precious memories at some time.
My date soon reached that point where she could hold back no longer and pounded away until she came. We were playing safe but I do so wish I could have felt her cum shoot into me. She pulled out and I removed her rubber and licked her cock clean, then shared it with her in a cum-smeared kiss. It was heaven.
She wasn't finished however.... but I'll save that for another post.
826 days ago
My first experience with another crossdresser also started in a chat room. He liked my self description and he had beautiful pic posted. We would chat about each other's fingers across the keyboard...then slipping on each other's thighs. He lived about 30 miles away and we finally set up a meeting.
7AM at a 7-11 on a rainy grey morning we met and sat at the table facing each other. He had jet black hair, small beard, strong and handsome and we were both equal straight looking in our street clothes. Blond, I unbuttoned one button on my shirt to show that I was dressed up underneath...he said he was too. He suggested we drive to a quiet corner of a park-and-ride next to the interstate and sit in his big truck, in the back seat. We undressed to our pretty underwear. He had on a black silky bra, panties and stockings and I had on all white silky panties and camisole. We made out like teenagers, groped and kissed and sucked and licked. Steamed up the windows wonderfully and finally I fucked him. Wonderful.
We got together another time, at his suburban house during a hot summer day. He dressed much more extravagently than I did. And we had a hot sweaty tryst in his bed room. He was getting divorced and moved out of town but we still occasionally meet in a chat room....I hope he reads this and knows how much I enjoyed being with him.
7AM at a 7-11 on a rainy grey morning we met and sat at the table facing each other. He had jet black hair, small beard, strong and handsome and we were both equal straight looking in our street clothes. Blond, I unbuttoned one button on my shirt to show that I was dressed up underneath...he said he was too. He suggested we drive to a quiet corner of a park-and-ride next to the interstate and sit in his big truck, in the back seat. We undressed to our pretty underwear. He had on a black silky bra, panties and stockings and I had on all white silky panties and camisole. We made out like teenagers, groped and kissed and sucked and licked. Steamed up the windows wonderfully and finally I fucked him. Wonderful.
We got together another time, at his suburban house during a hot summer day. He dressed much more extravagently than I did. And we had a hot sweaty tryst in his bed room. He was getting divorced and moved out of town but we still occasionally meet in a chat room....I hope he reads this and knows how much I enjoyed being with him.
844 days ago
Hi Stephanies... your fantasy is so hot and good. I love it. First let me say, there is nothing prettier that cocky in pretty panties. (i think). It is just to wonderful to see the bulge of the cock and when it hangs out.... OMG... i just love to see it. I absolutely love the idea of cuming in panties and then sucking the wonderful cum out. Its soooo hot sissy and completely perfect. I think it defines the kind of sissy cd you are, and i think it is so right to be that way. I am sitting here wearing a pink bra c cup forms and a little sleep outfit made my Candies (Britney Spears endorses them). I has the word Candies on the panties on the ass and on the bottom of the frilly top. But the best part my cocky is rock hard after reading your post. Id love to talk or chat with you anytime about your fantasy. (i have sucked cum out of panties before giggle and played alot of cum games). Id love to tell you bout them and hear more from you..... xoxo sb.. ps keep cummin in panties...Your a hot gurl!!!!!!!!!!!!!!!
872 days ago
Wow Rikki your story is so hot hot hot!!!!! I love that she is a bbw. Did she have big tits? I loved the passing of the cock back and forth and sharing it with a woman. MMMMMM that is so girlly and slutty. I would have loved to have smelled her panties and rubbed them all over my face and his too. (giggle). And just thinking about you wth your tongue in her big ass makes me soooooo hard. You are so sexy and girlly for doing that and I love it. Cant wait for more more more!!!!!!! xoxo sb... ps you go sissy girl
872 days ago
Thanks Rikki for the support. Your so sweet. xoxo SB ps i always careful in all respects giggle
872 days ago
Dear Sissybra,
I was sad for you when I read your post. I can't imagine what it was like for you to lose someone so close to you and that you knew so well. I also think how much you're missing that deeply satisfying sissy play time you had together.
You're story tells us all that it is possible to find that special friend that we can really be all of ourselves with..all of our sissy selves.
Thank you for sharing. I hope you make lots of friends here.
PS Please be very careful when you go out dressed. I don't want to be reading about you in the newspaper someday.
Hugs
I was sad for you when I read your post. I can't imagine what it was like for you to lose someone so close to you and that you knew so well. I also think how much you're missing that deeply satisfying sissy play time you had together.
You're story tells us all that it is possible to find that special friend that we can really be all of ourselves with..all of our sissy selves.
Thank you for sharing. I hope you make lots of friends here.
PS Please be very careful when you go out dressed. I don't want to be reading about you in the newspaper someday.
Hugs
872 days ago
Well I have had several sexual experiences over the years in various situations. I have met other crossdressers, some good, some bad. I have been to a female dom. I have met men in motels. I have done it in cars. I have even been to an adult theater once. It will take me some time to sort through them for you girls. One of my best ones was when I found another crossdressing sissy who enjoyed my idea of being a sissy. We did not do so much the frilly dresses and sub/dom routine. We were sissy lesbian girlfriends who love to act sissy and girlly. We were limp wristed and prissy, but our clothes ranged from everything. We really liked the kinda teen girl look with lots of girl shorts and cute little tops and girlly purfume. We would meet at his/her house and dress and priss all day. We would suck out little sissy clits and fuck our ass pussies. We really enjoyed each others cum. I love cum on my face. We would take turns cuming on each other, and then kiss the cum. It was so sissy and femmie. At different times and places we would partially dress and run into a convenience store and buy some tampons and would let the clerk see us kiss. Oh course you could tell we were bois, cause we might have on short shorts and girlly top with filp flops and and red lipstick. It was so thrilling and dangerous. But we had each other. Sadly, my sissy Gf died of cancer several years ago, so Im looking for another fun sissy playmate. Thats all for now. xoxo sb
872 days ago
I met her online in a chat room called upskirt or something like that. I took awhile to beleive that she was a woman and that she loved men in panties. It was the first woman I ever met like that. She lived about 15 miles from me. Her boyfriend, who wore panties and lingerie, live two states away. He was coming to visit her so after lots of emails etc we decided to meet in a hotel room and play together.
She was wearing a red bra and panties, she was a bbw, and he liked to wear three pair of panties and a cami. I wore panties, bra and half slip.
I changed in the bathroom. when I came out they were on the bed making out. I walked over to the bed and he came over to me to play with my panties and she did the same. Soon they were taking turns sucking my cock, passing it back and forth.
It was my turn to suck his cock. She and i sucked him together, first her then me. We watched his cock disappear into each others mouths.
I licked her pussy for along time while he knelt by her head so she could suck him. Some how she was laying on top of him and I saw that big gorgeous ass and knew that I was going to fucj her asshole with my tongue. I didn't know if she would like it or even let me but I was going to try. I pulled her panties aside and slowly rimmed her asshole with my tongue. I waited to see what she would do. I heard her moan as she then pushed her ass back into me. I got more aggressive and soon my tongue was in her ass, fucking her and she was coming. She was moaning and coming so loud her boy friend tried to see what I was doing LOL.
More later....
She was wearing a red bra and panties, she was a bbw, and he liked to wear three pair of panties and a cami. I wore panties, bra and half slip.
I changed in the bathroom. when I came out they were on the bed making out. I walked over to the bed and he came over to me to play with my panties and she did the same. Soon they were taking turns sucking my cock, passing it back and forth.
It was my turn to suck his cock. She and i sucked him together, first her then me. We watched his cock disappear into each others mouths.
I licked her pussy for along time while he knelt by her head so she could suck him. Some how she was laying on top of him and I saw that big gorgeous ass and knew that I was going to fucj her asshole with my tongue. I didn't know if she would like it or even let me but I was going to try. I pulled her panties aside and slowly rimmed her asshole with my tongue. I waited to see what she would do. I heard her moan as she then pushed her ass back into me. I got more aggressive and soon my tongue was in her ass, fucking her and she was coming. She was moaning and coming so loud her boy friend tried to see what I was doing LOL.
More later....
875 days ago
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