Crossdressing a Life

All characters in sexual situations are 18 years of age and older.

I am a 62-year-old lifelong crossdresser, I use various internet sites and I have told snippets of my story here and there, so I thought I would write them all in one place.

I joined the military, we used to go as a group to the base swimming pool and muck about. There were some Jordanian students there at the same time, they used to mess about with us in the pool, climbing on our backs and pushing us under. One of them took a shine to me and would always single me out, all of this was going on between friends at a time when homosexuality was still illegal in the military. One day my friend climbed on my back, and I realised his cock wasn't in his trunks, so as he pushed me under, I took his cock in my mouth it was only for a second, but I loved it, nothing else happened and although I saw him at the pool again, that was that. I did fantasise about what may have been.

Life moved on as normal until I met a girl who would become my wife. I told he of my love of nylons and one night as we left the pub, she slowly lifted her skirt and revealed she was wearing a white suspender belt and tan stockings, I was hooked. We used to meet in my room for sex and one night she brought two sets of stockings and suspenders we wore a set each and made love all night.

Once we were married, she would indulge my habit and on occasion would dress me then make my face up in full make up and put a wig on me. She didn't mind me dressing but, said that when I was in make-up and a wig I looked like my mother, and she did not like that. So, the make-up and wig just sort of stopped. We spent a few years dressing up for each other, but once she put some weight on, she was not keen on dressing-up herself.

When I discovered the internet everything changed. I still dressed for my wife, but I started chatting to other dressers online.

My first ever meet was with a gurl called Zoe, we chatted online for some time, she said I needed a girl's name, so I suggested she choose one for me and so Tiffany was born. Our first meet was a weekday lunch time, we met in a garden centre care park, chatted briefly, then I followed her to a remote location. Once there I got in her car, and we kissed. We both pulled down our trousers, Zoe was wearing Black Fishnet Stockings with sexy red panties under slacks and a dress shirt, I had on hold up stockings and sexy panties. We kissed and Zoe went straight for my cock, she sucked me so well, when I returned the favour Zoe had a fat cock with a large bulbous head, but the most surprising thing for me was her pre-come, there was loads, she was so wet, I licked it all up then sucked her to orgasm, she then returned to sucking me.

My second meet was with a lady called Pauline. Pauline was in her late sixties and lived in Newcastle. We chatted for a while and exchanged pictures. Pauline was a very tall slim elegant lady, who used to visit with a group of ladies in Edinburgh, she shared lots of sexy pictures of her visits, which were quite explicit. After seeing these pictures, I assumed Pauline was out of my league.

I was very excited when Pauline agreed to meet me, I could not wait to visit her home. On the day of my visit, I showered and dressed in sexy underwear then but on my male clothes. I drove to Pauline's at the agreed time.

Pauline lived in a small block of flats, on the ground floor, she buzzed me in the main door and had just her head around her front door, she was fully made up but without a wig. Pauline welcomed me into her bedsit and offered me a drink, we chatted and as we talked Pauline put her short blonde wig on and I got to look at her properly. Pauline was dressed very eloquently in seamed stockings, black court shoes a mini skirt and a nylon frilly blouse. I told her she looked stunning.

I stripped out of my male clothes right in front of her, she could not keep her hands of me.

I dressed in a mini skirt and white blouse, red strappy high heels, and a cheap blonde wig.

We sat together on her bed settee, and we kissed and caressed each other, Pauline stood up, lifted her skirt, and lowered her panties, I went straight to work sucking her cock. Then Pauline knelt between my legs and started to suck my cock.

At Pauline's suggestion we pulled out the bed settee and lay together on the bed, after more kissing and caressing, and lots of nipple play Pauline got on all fours and asked me to fuck her.

I knelt behind this glamourous elegant lady and began to slide my cock into her bottom, her bum was quite tight and felt wonderful on my stiff cock. I fucked Pauline for what seamed like hours, she squirmed and moaned the whole time, then she had a huge orgasm and came in her panties. Pauline then sucked my cock until I came in her mouth, she then licked her lips and greedily swallowed my come. We kissed and I tasted myself on her lips. We then chatted some more as we calmed down. After I changed Pauline swapped her high heels for some fluffy pink slippers and I was shown to the outer building door with Pauline still fully dressed and made up, if a little bit dishevelled.

My third meet was with Kirsty, this gurl lived in Bedford and was able to accommodate. I arrived at her door to be greeted by a 65-year-old gurl partially made up, she had on shirt and trousers, but was wearing heels and full make up. Once inside I was shown to the spare room and allowed to change, when I walked in the living room Kirsty was fully made up and gently began to seduce me. Kirsty was a widower, who explained that when her wife was alive, they would frequent swinging clubs and she would get a kick out of watching men fuck her wife and she would clean them both up afterwards.

Kirsty was into bondage and discipline; she had the most amazing nipples which where large from many years of using nipple clamps. I would bite them quite hard which turned her on so much. I met Kirsty two or three times and we always had fun with each other.

After Kirsty I met my first admirer a lovely kind man who I have written about in the story My First Real Man.

Next, I chatted with a girl named Jenn, as neither of us could accommodate we arranged a car meet. We drove around for hours trying to find a secluded spot, finally we found one. I joined her in her car as soon as I had her cock in my mouth a police car came around the corner and we both got spooked and said our farewells. Not at all how I wanted the meet to go.

I sort of gave up on meeting after that. Until I was contacted by Carol. Carol was an older lady who was a widower but still had all her wife's clothes. In all her pictures she was wearing rather old fashioned but immaculate clothes. We met at her bungalow near York. After I changed, we were both fully dressed, Carol had net curtains up in all the rooms, so she left the curtains open. We were sat in her bedroom looking at sissy porn, when a lady postman knocked on the front door, which was right outside her bedroom window.

I don't know if it is common knowledge, but when you stand close to a window with net curtains you can see right into the room.

We both froze, I was panicking like mad, then Carol started to fondle my bottom. So, there we are two older transvestites stood about three feet away from a woman in her forties and I am being groped by a woman who should know better.

He asked me if before I left would I come on his cock and just pull his panties up, so after he had given me a blow job, that's exactly what I did, I wanked over his cock, pulled up his panties and told him to keep them on until the morning. I then changed into male mode and left.

I moved around a lot with work, I was living in Wales when I contacted a gurl called Lynda, she was in her mid-sixties and a very sexy gurl. Lynda informed me she had a boyfriend who visited her about once a month for sex and they had agreed that her boy pussy was his only, so anal sex was not on the menu, I agreed not to ask for anal which she thanked me for being so understanding.

We arranged to a meet at her place, I showered and was dressed in some sexy undies under my male clothes. On my way to Lynda's, I stopped at Tesco and bought myself a new silk blouse, a bottle wine, and some flowers.

I knocked on Lynda's door and when it opened there stood a full-figured lady dressed in a miniskirt and pink blouse, she had such a sexy smile. I stepped through the door and Lynda immediately kissed me. I gave her the flowers and wine and we chatted, then I went upstairs and changed into a miniskirt and my new blouse, I went downstairs, and Lynda just said "wow". We sat and ate a light meal together; I could not keep my eyes off this older sexy lady.

Once the meal was over, I caressed Lynda's nylon clad legs, I then stood over her and played with her nipples whilst we kissed.

We then moved to the sofa where we sat facing each other and continued kissing, I then slid to my knees and lifted her skirt, I leaned forward and kissed the tip of her nylon clad cock, I was in heaven. I pulled her panties to one side and swallowed her whole cock, she moaned softly.

Lynda then stood and bent over showing me her very sexy bottom and asked me if she had a nice bum. I stood behind her and caressed her bottom, then I knelt behind her and kissed her bum cheeks, then I parted her bottom and rimmed her sexy little rosebud, I placed a finger in her and kissed her bum cheeks, as I fingered her, she reminded me of her no anal rule and my promise. I continued to finger her to a wonderful sissy orgasm, Lynda went weak at the knees.

When I left Lynda thanked me for being understanding and asked, I would like to visit again.

I asked if I visited again could I kiss her panty clad cock? This was agreed upon, on every subsequent visit, Lynda would welcome me in, lift her skirt and receive a kiss on the tip of her cock.

In between visits I kept up some correspondence with Lynda and we both agreed we would like to have a threesome with another girl. Lynda managed to organise a meet with another girl.

I arrived at Lynda's at 7 knowing our other guest would arrive slightly later.

We sat in Lynda's both dolled up to the nines, when our guest arrived, we introduced each other, and our guest went upstairs to change. When she came back, we sat on the settee with me in middle with a girl either side of me kissing and caressing each other. Then Lynda knelt in front of our guest and sucked her cock. Lynda then went and sat in the other chair whilst me and our guest kissed and cuddled, I sucked on her nipple and looked across at Lynda, she had one hand rubbing her nipple and the other hand rubbing her crotch, it was the most erotic scene I had ever witnessed.

I met Lynda many more times over the next couple of years, I had real feelings for her.

My next meeting was with a married couple who were in their late sixties, and Lee was a bi crossdresser. When we first met his wife had a pot on her leg and would not be playing. We met at their house; we were both in male mode he went to his room to change, and his wife directed me to their spare room. I entered the living room to find him sat on the settee fully dressed, his wife was sat in an armchair, he asked me to sit next to him. We chatted for a while, his wife was very interested, we then started to kiss and cuddle. His wife then said, "It's time you two ladies went to the bedroom" Once in the bedroom we kissed and caressed each other, then embraced in a sixty-nine until we both came. He left me to change and went back to his room. Once back in the living room his wife asked me if I had enjoyed myself and would I like to come back again. We then all three of us chatted over a cuppa and talked about everything including sex.

On my next visit Lee met me at the door fully dressed, and welcomed me with a loving kiss, we sat together on the settee, me in male mode and lee fully dressed, the wife was sat in her usual chair. After a short time, Lee took me to the spare room, this time he stayed and watched me change, he loved it when I dropped my jeans to reveal panties and hold up stockings, once I had changed, we kissed then climbed on the bed. We kissed and stroked each other, and Lee's wife came in and started to caress us both, she massaged my bottom then started to finger me. As I kissed Lee his wife was fingering my boy pussy, she then started to insert a ten-inch dildo into me, as we played his wife fucked me until I had a lovely orgasm.

Once the dildo was removed Lee asked me to fuck him, I stroked his bottom then fingered his pussy until he was ready for my cock, I entered him slowly and then fucked him until he came. We lay together and it was only then I realised his wife was still in the room and had watched the whole thing.

After I changed back to male mode we chatted over a cuppa as if what had just happed was nothing unusual.

My next meet was another car meet, will I ever learn? This time it was properly planned.

I met Alana on a deserted road in the middle of nowhere, I climbed in her car, and we chatted then kissed and cuddled, the suck each other's cocks, whilst Alana sucked me, she fingered my bottom which turned us both on.

Just before I left Wales, I was fortunate to have a meet with Gina. I met her at her lovely home where once I was changed, we got to know each other, lots of kissing and caressing and cock sucking, then Gina fucked me with a long dildo, we had a wonderful night together I just wish I had met her sooner.

After I moved back to the north of England, I tried to give up on meeting crossdressers, so I started to look for a lady escort would meet my needs. I found a lady who was in her late fifties and gave massages. We discussed at length my interests and I settle on a massage with prostate massage too.

When I arrived at Jean's house I was shown upstairs and once I had carried out the paperwork I stripped and lay on the table on my back with my rock-hard cock pointing up.

Jean stripped down to just a pair of hold up stocking and panties and proceeded to massage me from head to toe, talking to me the whole time, I caressed her legs and bum. Then Jean massaged my prostate and wanked my cock until I came shooting sperm up into the air.

I continued looking at all the crossdresser and swinging sites and eventually was contacted by an older gentleman in Newcastle, I cannot remember his name, but he had lots of sexy pictures of him entertaining various crossdressers. We chatted for a bit then agreed to meet. He lived in a tower block of flats in the middle of town. I arrived on time, and he buzzed me in, we chatted some, then he showed me to his spare room and allowed me to change. I dressed in seamed black stockings, high heeled shoes a knee length skirt and blouse. When I walked into the living room, he was completely naked and stood next to the sofa. He was a big man slightly overweight with a big belly and barrel chest. I walked straight up to him and kissed him; he kissed me back and we both started exploring each other's bodies. I sucked his nipples and then knelt on the floor and sucked his big fat cock. He led me to his bedroom, and I lay on my belly so he could spank me, then he lay on the bed, and I sucked him to completion.

One day I was bored, I was wearing stockings and panties under my jeans and decided to look for a cottage. I stopped at some toilets north of Amble and went in to pretend to have a piss. There was a chap inside who asked me if I wanted some fun. I agreed and we went behind the toilet block. We kissed then both dropped our trousers, he did not comment on my choice of underwear, just proceeded to give me a wonderful blow job, when I came in his mouth, he just spat my come onto the floor. He then asked me to wank him, I offered to blow him, but he said no. So, I then wanked him off and pointed his come to land where he had spat mine. Afterwards he told me he was not into the crossdressing thing but went ahead with our meet as he was so horny.

I started to correspond with a crossdresser in Ashington called Davina, we seemed to hit it off. A meet was arranged at her home. When I arrived, Davina was fully dressed and made up. She looked sexy. I was introduced to Davina's wife and after a brief chat I was shown into the downstairs bathroom so I could change, I had girly undies on under my male clothes, so I changed into a miniskirt and frilly white blouse. When I returned to the living room, Davina just said "wow" then her wife very kindly told me I looked very nice.

Davina kissed me and asked if I was ready to go upstairs.

Once upstairs we got straight to it, Davina had told me in our correspondence that once she got going, she went at it like a steam train. We made love to each other I fucked her first, then she fucked me. Davina wasn't wrong, she fucked me on my back then doggy style, I had never experienced anything like it before, she was so good though.

I was left in no doubt that I had been fucked.

We went back to the living room and chatted, then I changed, and it wasn't until later that Davina informed me, I had left my white frilly blouse on the back of her bathroom door. I should have gone back for a return meet, but the opportunity never arose.

I then met another admirer called bear. He liked to meet outdoors, so we met in a church yard. I had my now usual choice of underwear on, and we met at the agreed time we had a long kiss and a cuddle before giving each other a lovely blow job. He even showed me around a nearby cottage.

Then I went for another visit to Jeans. This time I asked if she minded me wearing stockings during my visit, she assured me this would be fine. Upon arrival I was shown into her massage room and stripped down to my black hold up stockings.

Jean came in and was again wearing hold up stockings and panties, she proceeded to massage me from head to toe. Having my legs massaged whilst wearing my stocking was a wonderful feeling. Jean then massaged my prostate whilst wanking my cock, I had a lovely finish.

I then moved to Swindon where I continued to look for other crossdressers, I had two meets with an older crossdresser, both were alright, but I was feeling under the weather at our first meet and only managed a blow job. Then at our second meet he was unwell, so we both dressed at just sat and chatted, I quite enjoyed a relaxed evening.

I then visited Swindon's Gay Sauna, the first time I went there were lots of gay men there, I watched some gay porn then watched a threesome with three young men. I met a crossdresser who was in a separate room on all fours. She had a big dildo in her and her balls were tied tightly with a thick nylon rope. As I fucked her with the dildo, she asked me to pull on the rope hanging from her balls, I did this, but she wanted the rope pulling much harder, I could not believe the pain she was letting me inflict on her.

On my second visit to Touch there was a good-looking man in the sex sling being fucked by a much older, but very well-built gentleman. As he reamed this man I watched and was totally turned on. Then I noticed the man in the sling had painted toenails, I was intrigued. When the fucking was over, I approached the man in the sling and mentioned his nails. He said he was sissy but did not like dressing for the sauna. We went into a private room and kissed. I lay on the bench, and he sucked my cock and played with my nipples, when I came in his mouth he just got up and left me, alone.

My next meet was with an escort who was a professional master.

We chatted briefly, then I asked sir for a meet. Master was in his sixties but still very handsome and was happy to meet me.

I arrived at sir's house early and was shown into the living room, we chatted and established my limits, I wanted to be punished but left unmarked.

Master said he understood, I was told to undress and wait for him, Master put a DVD on for me, it was a gay film with a twink in a public-school uniform being punished by an older man. Not my usual choice of porn, but it still turned me on.