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Crossdressing Stories

Crossdressing Stories
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Monday, 21 September 2009
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  • This is fiction/fantasy, but I'll write it the way I've imagined it many times....

    My wife & I booked the holiday to a Spanish island, her no doubt looking forward to sunbathing, swimming, eating in nice restaurants. Me eager to surf the web to find out if topless or nude beaches were in the area of our appartment. I was delighted to find there was a naturist beach within a mile. I casually mentioned to her that there was a nude beach, & would she go? Amazingly, she said "yes, so long as there was no-one there we know". The week before we flew out, I took extra care to remove all pubic hair, as did she, but I don't think she realised just how keen I was to show off my little cock.
    We arrived & checked in to the appartment complex, doing all the usual mundane stuff like finding a shop to buy in food, water etc. Finally, after having a meal in a local restaurant, we could relax with a drink on the balcony. As we sat enjoying the evening sunshine, the couple from the next appartment, Graham & Jacqui, appeared on their balcony. We exchanged hello's, finding they had also arrived that day. I couldn't help checking out Jacqui, wondering what type of undies she was wearing. After a short chat, we all went inside to get some much needed sleep.
    Next morning, I was very keen to get down to the beach, but had to try not to look to excited or harrass Dianne (my wife) to go - just try to stay cool. Eventually I said "shall we go down to the nude beach?" I was surprised Dianne seemed so keen to agree, she usually keeps nudity strictly to behind closed doors. We headed off, with good supplies of sun-cream & cold drinks, and, after a 30min walk along the beach, the bikinis & shorts started to give way to boobies, then a little way further, cocks & pussies. I was pleased that not everyone was athletic looking, as though I'm not ashamed of my little clitty, I do have a bit of a belly! We walked a little further, & found a quiet spot, not too near anyone else, and settled down. As I was laying out the towels, I was amazed to see Dianne already undressing, i started to get a little aroused seeing her 36b tits & shaved pussy on display to the world. In no time at all, I was naked too, my clitty semi erect. After a while of watching the other people swimming, playing frisbee etc, I was feeling more relaxed, and back to my normal flaccid 1.5". I was sunning my back & must have dozed off, but came to with someone saying "hi". It was Graham & Jacqui. I thought Dianne would have been trying to cover herself up, but she continued lying on her back, propped up on her elbows, happily exposing her boobs & pussy to a couple we had barely met. My eyes immediately shot to Jacquis boobs, which looked to be a-cup, then her lovely looking pussy, shaved apart from a "landing strip". Then I had a sly look at Grahams cock. It couldn't have been any bigger than mine, and, was totally hairless. Seeing this, I rolled over, exposing my little clitty for them to see. Surprisingly, Jacqui laughed and said to Dianne "Wow he's tiny like Graham, let me guess, I bet he wears your panties". I was stunned & looked at Graham, who seemed a little embarrassed, but before either of us could say a word, Dianne replied "Yes, he wears my bras, tights, stockings & shoes too". I was horrified & didn't know where to look, but Jacqui just giggled & replied "Graham has more lingerie than me!".
    They sat down next to us & Jacqui & Dianne had a very long conversation about what we liked to wear & how we got so excited when we were dressed up. Graham & I kept very quiet, though I could see his clitty getting bigger, as was mine! The girls then started telling each other about the lack of satisfaction to be had from our little clits, but both agreed we were skilled with tongues, fingers & dildos. I was fully hard at being ridiculed by my wife to this sexy lady & by then had given up any idea of trying to hide my hard clitty. Graham seemed fully erect too, and, when the girls noticed this, they had us stand up so they could compare erections. Graham was slightly bigger than me by around half an inch. We spent the afternoon talking & the girls seemed to be becoming good friends. After a while, they suggested Graham & I went for a swim, to try to cool down our hard little cocks. We both headed to the water & I asked Graham did anyone else know he dressed, he said no, & asked if anyone else knew about me, again the answer was no. We went into the sea, & continued talking. He said he started out wearing his older sisters undies when she was 13 & he was 10. I told him I started with my mothers & aunts. I asked him if he'd ever sucked cock, he said no, but I thought he was lying. As Dianne didn't know about my bi-adventures, I also denied it. Eventually our erections subsided & we headed back the the girls, who were starting to get dressed. We dried off, dressed & headed back to the apartments. Dianne told me when we got back, that we were going out for dinner with our new friends. I asked her why she had told Jacqui that I crossdressed & couldn't satisfy her with my little cock, she just said "it was nice to meet someone I could relate to". I was stunned. I had a shower, as did Dianne, and we started to get ready to go out. Dianne looked stunning in a black bra & matching lace panties, hold-up stockings, a floaty little black silk dress & high heels. We met Graham & Jacqui outside the appartment, she was in a long white cotton dress & I could see her white bra & thong clearly through it. Dinner was pleasant, lots of small talk, then we walked back & Jacqui asked us to join them for a drink. We went inside & Graham poured the drinks. Jacqui then asked Dianne to go into the bedroom with her. We heard giggling, & a few minutes later they came back. Dianne said she needed something from our apartment & left, returning a few minutes later. The girls both went back into the bedroom and a few minutes later, called us in. There on the bed was two bras, two pairs of panties, two suspender belts & two pairs of stockings. I recognised one set as belonging to Dianne. I couldn't believe my normally quiet wife was part of this! The girls started giggling & said, "get dressed sluts, you in Diannes Graham, & you in Jacquis". They then watched uus putting on each others wifes lingerie, giggling at our hard little clitties. I said to Dianne & Jacqui "can we see you in your undies?" Amazingly, they both peeled off their dresses, and there we were, all in lingerie. Graham then suggested something I thought Dianne would go mad at, he asked the girls to wear each others undies, to which, to my surprise, they agreed. Watching my wife putting on another womans still warm bra & panties had me nearly cumming. I was about to start touching myself when Dianne said "No! I want to see you touch Graham" Well! I was stunned! My wife wanted to see me play with a tranny clit, all my fantasies coming true. I started to gently rub the front of Grahams panties, he did the same to me. I was dripping pre-cum, soaking the lacy knickers I was wearing. I could feel Grahams wetness too. I looked to my wife for approval & she just nodded to let me know it was ok.
    Jacqui said, "lick him Graham". He smiled at her, then fell to his knees & licked me through the panties, eventually pulling down the front & taking my hard 4" into his mouth. He knew how to suck cock! I looked at the girls and moaned that I was going to cum. Jacqui laughed & said "don't spill a drop you slut-whore" to Graham. Dianne giggled & said "when it's your turn, you won't spill any either, will you, you sissy faggot". At this, I came in torrents, Graham swallowing everything I gave. Graham opened his mouth to show he'd swallowed every drop, then to my surprise, Dianne kissed him, rolling her tongue round his mouth before telling Jacqui "yes, he's swallowed it all". Graham stood up & I knew what to do. I went down on his rock hard clitty like a starving man. I could feel his orgasm building, and as he told the girls he was going to shoot, he filled my mouth with sweet sissy cum. I gulped it all down & opened wide to prove it. Jacqui kissed me deeply, her tongue washing round my mouth, before she too was happy that I'd drank all Grahams cum down. I stood up, next to Graham, both of us limp & drippling. "Lets show these sluts how real girls cum" said Jacqui, & reached for Diannes tits. I though it would end now, Dianne has never shown a bi side, but, she reached back to start touching Jacquis boobs too. They tumbled onto the bed, kissing, before rubbing each others pussies. Jacqui then spun round and lowered her pussy, still in Diannes knickers, onto her face, then buried her head in my wifes crotch, still in Jacquis panties. They brought each other to orgasm, the invited us to join them. The rest of the night being spent licking & sucking whatever was nearest. The holiday of a lifetime!
    groups.wall 532 days ago
  • Hello pantyboy, Its been a long time sense we have chatted. I had to tell you about my visit to mom's in Iowa.
    We had a family reunion this last weekend, sense it has been 15 year that I have been to one I flew to Iowa to visit.
    It was just me , wife could not come. Mom said I should stay with her. Well she picked me up at the airport in Ceder Rapids,and we
    drove to her place, she lives alone in a two bedroom town home. When we get there I expect her to tell me to put my things, which consist of one suit case
    with 2 days of cloths , including my silkies (bras , panties ,stockings, slips, and of course nighties to sleep in ) in her extra bed room. To my surprise
    she offers me to put them in her own room. My heart jumps out of my chest! here I'm expecting to maybe sneak in her room and go through her pantie drawer
    but no she offers me complete access to her entire room ! everything , including her bed. I can not tell you how excited I was. I immediately tell her I'm tired from
    the flight and want to go to bed. She says ok and kisses me good night. Well I wasn't in her room for two seconds with my cloths off and I was in her panties.
    Oh pantyboy it was heaven !!!!! I spent the rest of the night trying on all I mean all of her slikies and dresses, and I didn't ever worry about putting them back neatly.
    I wanted her to know I was trying everything on. The most exciting part is I found after much searching my favorite nightie of hers that she wore on her wedding night
    50 years ago a Rogers chiffon full length blue nightie. The one I wore ever sense I was a very young pantyboy, along with a vintage VF half slip with 6" pleats at the hem,
    also one she wore on her wedding. Which I have worn forever. I don't know why she kept these , but they were in her ceder chest wrapped in tissue paper around her wedding dress.
    I have had many wet dreams putting on both of these silkies. So to find them on a night that I had complete access to them and all her slilkies was heaven. So of course I went to bed
    with her panties , bra, stocking at the lovely Rogers Nightie. Of pantyboy I was cumming in minutes !! I cam in her panties so many times that first night mmmmmm.
    In the middle of the night I got up to go to the rest room of course still in her nightie ,with a beautiful chiffon robe I brought with. Going down the hall to the bathroom I hear the door the bed room
    she was in open and mom steps out, here I am in the dark hallway in her nightie and all her slikies . I freeze wondering if she can she me, there is a night light in the other room so I thing maybe
    she just saw a silhouette . She says are you ok honey? I say yes just need to go potty. She says ok night dear. I don't know if she saw me or not but if she did she didn't say. I was sooo hard in that
    moment I immediately went to the bathroom and came in her panties. Oh pantyboy it was sooo wonderful !!! standing there in her silkies in front of her. I will cum many times thinking of this.
    That is not the best part , this went on for two nights. Hours of dressing in all her slikies, and cumming and cumming in her panties and her bed. But when it was time to leave Monday, I packed that pretty nightie and
    and halfslip and a couple of pairs of her panties for my trip back to Ky. I decided that those were my birthright for all the years of dressing in her silkise. I don't know if she wrapped them in that tissue around her wedding
    dress to save them for me or not , but I don't care . They are mine now. I am setting here at my computer in that pretty blue nightie , in her panties writing about my wonderful weekend in mom's silkies . A dream cum true!!!
    Oh pantyboy it would have been wonderful to have you there with me to spend the weekend in mom's silkies with me. mmmm thats another dream !!!!



    Panty kisses !!!
    groups.wall 569 days ago
Hi, this is SissyBra and I'm creating a story group about Crossdressing. Now these stories can be true or fictional. The only concern is not to post any copyrighted material. Now with that said, here are a few ideas. A fictional story about one of your hottest fantasies. A true story of an adventure you had crossdressing. Any sex story that turns you on. A story about your your clothes and your wish list. A story about how sissy you. A story about you and your wife and your crossdressing relation. Whew... I can get long winded sometime!. But you get the idea. Try to keep them to the crossdressing theme if you don't mind. But most of all. Have fun!!!!!!
There are no announcements yet.
I was buying a couple of pairs of LovePats panties for myself one time at a local drugstore, and the checker said "oh, these are really comfortable, aren't they?" I just smiled at her and paid for them.
Last replied by amber_c on Monday, 16 April 2012

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