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I don’t travel much these days but when I stay away overnight I always try to book a gay B&B or guest house from the web. A couple of times in the past I‘ve got lucky with one of the other guests.
Last week I had to go over to North Wales for the morning funeral of an old friend so I booked a room for the night before at a small B&B in Conway that was advertised as ‘gay owned’.
I arrived there about 8pm and was met by the owner, a slim … Read more...

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I am a Tranny, NANCY by NAME, and NANCY by Nature, if you know what I mean, Well I went for a walk in SMESTOW VALLEY LOCAL NATURE RESERVE Near TETTENHALL last night at 9PM all DRESSED and ready for enjoying myself and as I walked through the woods I met a man who was standing and as soon as I got near him he started walking in front of me and occasionally looking around at me anyway he then walked of to the side and into a glade and vanished fro… Read more...

I had been feeling horny for quite a few days and today was no different but had an errand to run so decided to dress up a little. Had a nice long bath and shave all over, red nail polish on, perfume and slipped on a black bra and tight black lacy camisole. I pulled up my lace topped stockings and my black suspender belt and then slipped on my pink satin thong that I had borrowed from my twenty something next door neighbour...,mm I felt so sexy I… Read more...

Crumbs! It has been a long time since I have written up any of my adventures, A lot of this is because I am now in a very close and loving relationship with another tranny and she prefers that I do not broadcast our activities, However, this is a story which happened just last week and did not involve her at all, so I guess that makes it fair game?

I have curtailed a lot of my rather excessive ways but last week i had arranged to meet a guy in… Read more...

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My ex took great pleasure in making me put on sheer tan pantyhose...pink frilly sissy panties before applying my favourite coral lipstick to my luscious lips....she would then laugh as my little sissy cock grew to its full pathetic size under the sheer nylon...l would soon get very wet as she started with the verbal insults....usually " you pathetic sissy with a little chip " then would come the spanking with one of my pink mules slippers...over … Read more...

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Some weeks passed since my first encounter with Jane and Eric - I half expected never to hear from them again , consoling myself to occasional wanks whilst re living the erotic meeting.

Some weeks later I was browsing SH , when I noticed a message in my inbox . I opened it to find it had come from Jane!
I was so excited to make contact again and quickly read on. She said Eric and her were planning a party for a few friends at their studio … Read more...

My elderly neighbour has been having anal sex with me for years and I have blown him so many times I have lost count. A few weeks ago he bought a Manrammer dildo to use on his regular guys who he sees. It's a bit of a monster dildo with a nice handle for ultimate control in an anus.

Most of his fuck buddies can't take the Manrammer but I am lucky enough to be able to take it at a stretch. I like the fact that he can administer it to me while h… Read more...

Went to Primark to look in the sales and found a lovely mini dress and some heels. Got home bathed, shave my legs and anywhere else hair was sprouting from.
Slipped my nylons on and a bra. Slowly slipped into the new dress! oh my god it was so perfect. Heels on, lips on and out the door.
Made my way to the local cruising area in Stoke to see what was occurring as I was really horny.
When I pulled up i for out and adjusted my dress as it had ri… Read more...

On Wednesday I had booked a travelodge with the plan to go out on a date however as a back up I advertised myself as a dressed sissy for visitors. The date didn’t materialise so there I was dressed in my shirt black long sleeved bodycon dress, black ups and lingerie. Didn’t put my heels on to start as I applied make up pink nail varnish and my wig.
So a message came through off another site he was 30 mins away, I gave him the room number wh… Read more...

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I heard him come back in the house, I could tell he was not alone, my guess was there where four of them. It is a known thing that if you cannot see , your other senses pick things up, but I was surprised how quickly the effect worked. After all I had only been blindfolded for a matter of a couple of hours. "oh fuck" my mind raced.

Well I had been with a couple of guys before, surely a couple more was not that bad, I was trying desperately… Read more...

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Dave had been a star, he was always there for me in spirit if not always in person. He visited as often as his work load allowed, and every time he left I begged him to stay but deep down I understood why he could not.

As soon as I felt fit enough, I started to go to West Hollywood and Silver Lakes again, mainly for the company of my old friends. Every now and then the fun would move from the whatever club we were in and we would migrate to s… Read more...

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Within six months of Ruth’s death, we were back in Birmingham for dad’s funeral, we had been getting on a lot better since I moved to the states but we still couldn’t work together.

I really wanted to keep his company, and seriously considered moving back, but after months of discussions with lawyers and accountants found it would have been detrimental to the people who worked for dad, so I decided to sell up, they all kept their jobs.
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Chrissy was a gem. I had admitted that I liked to dress, and she admitted that she had known from day one, Ruth had told her about the ‘three amigos’ thinking nothing was going to come out of the meeting but hoping that Chrissy would be up for it.
We were renting an apartment in a place called Fruitdale, (which we both laughed at as it seemed appropriate) in San Jose, I was working for a software company in Silicon Valley and Chrissy was wor… Read more...

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I had arranged to meet a guy at his house in Plymouth, he said it was just off a busy main road and there was plenty of parking in the street so I left my house at 5 and drove to somewhere quiet to change, as usual I slipped my butt plug in then put on a thong and matching bra, my hold ups and 5in stilettos, as agreed I wore a sexy long sleeve white blouse and a tight under bust corset along with a very short flippy mini skirt that just about cov… Read more...

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Home life in the early 80’s turned to crud for me.
My brother Tony died aged 27 after coming of his motorbike and hitting a lamp-post. Mum never got over his loss and died of what I truly believe was a ‘broken heart’. Dad took neither death well and that was the beginning of the arguments. So apart from work I just stayed out of the way, and sat in my room building my own computers and programming simple games (Chess, backgammon even my ow… Read more...

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Saturday afternoon was confession time for the three of us.
Ruth told us about med school and all the drinking, whenever possible 5 or 6 of the med students would go into London and basically just get pissed, several times things had got out of hand and they had all ended up on the floor or in bed in one or others digs, so she had experienced both men and women.
Dave had just had a couple of girlfriends, nothing too serious.
I bit the bullet a… Read more...

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My two best friends, were Dave, the lad who first showed me a photo of a man sucking a cock, while I was lying in agony with a broken leg. He lived about 3 doors down from me. Three doors the other way was Ruth, the girl whose brother had caught us playing dress up in her room when I was about 5. People in the street called us the three amigos because we were never apart.
By the time I was about 21 the aids crisis had hit Britain, I had been ca… Read more...

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I left school with 2 average ‘A’ levels, not enough to go to university, just as my older brother left uni with a first in engineering so he joined dads company while I went off to polytechnic. I started an HNC in engineering but found I had a real talent for computer programming so I after 3 years I had HNC’s in both engineering and programming. Every weekend was spent at dad’s company ‘learning the trade’ so rather than being paid I… Read more...

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I decided I would go out somewhere in public so headed to Torquay, I put on matching sexy underwear, a loose fitting cold shoulder top, bum hugging tight shiny leggings and my stiletto ankle boots, along with my butt plug, hair and make up done, anyway I parked the car and headed into town, as I was walking through a man came up and offered me into a club, I wasn't planning to but went in, there was lots of people, gay, lesbian, tv/cd's, I went t… Read more...

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I do not know how many cocks I sucked or how many loads I had swallowed in my 18 months of visiting the layby, but it must have been well over a hundred, but I still had not been fucked. I think this was because although I loved sucking cock I just did not fancy any of the truckers who in the main were smelly, unwashed and fat.
Fortunately, one of the drivers (one of the few who spoke to me) asked me if I ever used the local park sports fields?… Read more...

I was lucky enough to get out for the night to dress and have fun, I had ordered a pair of stiletto ankle boots and they had arrived the day before, anyway as usual I arrived up at coliford lake about 8 to 8.30, found somewhere quiet to transform myself, I first slipped my butt plug in and then put on sexy matching underwear then my tight denim leggings and my new stiletto ankle boots and a sexy black cold shoulder top, on went the hair and earni… Read more...

It had been about 2 months since Bill had introduced me to the pleasures of sucking cock (his). I had become more and more excited at the thought of dressing up and being Bills cock sucking girlie. Looking back I had become like an addict needing a daily fix of Bill's hot cock and the creamy cum it supplied every time I sucked it.
I could not wait to go round to his house and enjoy the feeling I was getting by dressing in the chosen outfit Bill… Read more...

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I recently stayed in barnstaple and arranged to meet a local man, that evening I painted my nails, put on sexy matching pink bra and panty set, sexy grey top, think black pic belt loose on my hips, popped my butt plug in then some sexy cheek hugging leggings and knee high boots, I did my make up, put my wig on, earings and a sexy neck choker, at 9 I went out to the car park and met him, he pulled me tight and squeezed my bum, he felt the end of m… Read more...

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I was out dressed again recently, again I went up to coliford lake my usual haunt, I quickly found somewhere quiet so I could get dressed up, I put on my sexy thong and padded bra then my opaque hold up stockings, I then put on my tight short choker dress and 5in stilettos, once dressed I applied my make up, lipstick, earnings and made myself into a wanton sexy slut, I then drove to the main car park where a car was already parked, I noticed a co… Read more...

Have only written one story before (losing anal cherry while crossdressing - under different name) but I had so much fun yesterday I felt I had to put this down.
Had an appointment in Newcastle with work and ended up at the Metro Centre at 9am. Had already spied on Primark's website a nice suspender belt so went in for a browse. I usually get a bit nervous buying lingerie but felt ok and picked my size, paid for it and walked away with a black l… Read more...

Once through the front door the old man ordered me to go up the stair to his flat . I pushed the door open to reveal what looked like a photographic studio. A tatty bed with a pink shiny satin like cover was surrounded by photographic lighting. In the corner was a hanging garment rail with lots of women's outfits from dresses to lingerie
Next the bed was a small table with an assortment of sex toys clearly the old man and Jane had a set up the… Read more...

A few years ago , there use to be some remote public toilets in the Malvern hills area which I loved to frequent on a Sunday afternoon for a bit of fun. Usually I would get dressed up only to find at best a quick handjob at the urinal and the blokes hardly noticed the fact that I had lingerie under my jogging bottoms.
However on one occasion I was feeling really horny. It was a Sunday afternoon in November and not much was happening at home, s… Read more...

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Placed my first Swinging Heaven advertisement for a long time today and then headed off to the Black Swan layby and then onto Royal Oak layby after finding the Black Swan layby unproductive.

Dressed in a black see-through top, short sexy skirt, six strap suspender belt, stockings and girly shoes with a stubby short heel, wearing mascara and slutty bright red lipstick, I was on the hunt for cock, any cock as long as it was clean and safe to enj… Read more...

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I have been dressing for so long and was very eager to meet another tranny for some sex fun, I tried endless adverts no luck I then saw an advert from a really sexy ladyboy escort, we agreed a fee and I nervously drove to her flat. With my undies in a bag I paced outside her flat then found the strength to knock, when she opened the door she was so sexy we had a quick chat and I was already getting hard as she was in a black basque, stockings and… Read more...

I’d only started talking to John, our neighbour three doors down a couple of months ago. As I was passing his house, he mentioned seeing my wife Ann, in the shop where she works and it led on to him recognising me that day. Since then, we’ve exchanged pleasantries on a couple of occasions and we even put the world to rights chatting outside his house or outside mine.

John is a couple of years older than me (I’m 59), he’s quite imposing… Read more...