JollyJohnnyP's Blog - page 1

Some years ago I went to a TV party in London where the theme was "End of Term" so I put on my bottle green gymslip over my bottle green school cotton interlock knickers and white blouse, not forgetting knee-length white socks, black shoes, wig and old national health glasses for a studious look. I was unaware that there would be a competition but an hour or so after my arrival, a man dressed as a schoolmaster complete with gown and mortarboard announced "Will all schoolgirls parade around the dance floor". I was unaware that this was a competition to be judged by a panel of three 'schoolmasters'. Initially no-one showed any signs of obeying the instruction but then a lone real female 'schoolgirl' walked onto the dance floor and I thought "If she can do it, so can I". I joined her and soon all the 'schoolgirls' were on parade, including a reluctant friend of the first girl whom she and I dragged into the parade. As we passed the group of 'schoolmasters' we were asked our names. After about three circuits of the dance floor we were told to return to our seats. A brief conference among the schoolmasters was followed by the announcement of the winners beginning with the winner of the third prize. Although I heard the announcement, "Third prize, Joanna", the idea of winning a prize was so out of my mind that a friend I was sitting with had to tell me, "That's you!" before I realised that I had won third prize in this "best dressed schoolgirl" competition. I went out onto the dance floor to collect my prize and was told to do a twirl in front of everyone. I obeyed, flaunting my school knickers (which the gymslip wasn't quite long enough to hide anyway) and coming away with two bottles of wine for my efforts.

The one thing which would have made the evening perfect would have been to receive a good fuck from one or more of the schoolmasters who judged us. As it was I was so high that I put my coat in the boot of my car and drove home blatantly in my school uniform. However, after about 20 miles I realised I needed a pee. A motorway service station was out of the question with me in my schoolgirl uniform so I left the M1 for the A5 (the Roman road Watling Street) but it was remarkable how much traffic there was (at midnight) making a roadside stop very risky. I was getting very desperate by the time I found a secluded lane and I just managed to get out of the car in the entrance to a field before the dam burst and I flooded my knickers like a naughty schoolgirl. Fortunately I did have a spare pare of panties with me so I didn't have to stay wet for the rest of the journey home. However, the wetting accident did round off the evening nicely in true schoolgirl fashion.

I was a regular at the gym, not a fitness fanatic, just keeping myself in trim. I always wore figure hugging lycra tops and thigh length shorts as I enjoyed showing off my physique. I had noticed occasional interested glances from a slim guy in his late 30s but nothing more until one day he appeared with an attractive woman of similar age. I noticed that she too kept glancing my way while they seemed to be having an argument. Eventually the woman came over to the cross trainer I was using, introduced herself as Jill and asked if she could have a word with me. I agreed and we went over to the cafeteria for a chat. She explained that her brother was gay and very much fancied me but he hadn’t the nerve to make a direct approach as, although he suspected, correctly as it happened, that I too was gay, he was frightened of “coming out” to me in case I was straight. He’d talked a lot about me to his sister who finally came along to see this fanciable guy for herself. I thanked her for helping her brother, for her straightforward honesty and explained that he was right in thinking that I was gay. I also explained that I didn’t have a partner and would be willing to spend an evening with Alan, her brother. She asked if I’d mind her being present to which I replied that it wouldn’t bother me and we arranged to meet the following evening at the flat which they shared. Jill had explained that Alan would be very nervous about meeting anywhere other than at their flat and so it was with a high level of curiosity that I arrived at Jill and Alan’s flat at 7 pm the next day.

I had brought with me a holdall containing a variety of clothes from tight lycra gym outfits to softer silky garments, many of which were women’s as I found women’s clothes were generally softer, thinner and more sensuous that male attire. I was dressed in a maroon and blue track suit so as not to arouse too much speculation by the neighbours but once inside I removed the track suit to reveal myself in a very thin tight white semitransparent pair of shorts and matching teeshirt. The outline of my genitals was clearly visible through my shorts, as was the fact that I was wearing nothing underneath. Jill exclaimed at my outfit and showed me into the lounge where Alan was sitting on the sofa, also clad in lycra, so I sat down next to him and felt his thigh rub against mine. I responded with firmer pressure and was pleased to see a growing bulge in the front of his shorts. I ought to mention that Jill was also dressed in lycra, a skirted leotard in pale pink which showed off her breasts to advantage yet the skirt concealed the intimate details of her crotch and whether she was wet between her legs. “Alan, ask him if you can feel his shorts!” were the next words Jill spoke and before Alan could ask I replied, “Of course you can and I’d like to feel yours too.” Suiting action to the words I started stroking Alan’s thigh through his shorts and he was so aroused that he had to reach inside his shorts to adjust the position of his penis which was by now becoming a rampant rod of flesh. As I felt Alan’s hand sliding up my thigh, my penis was also swelling and I decided to provoke Alan even more so I got up and bent over, flaunting my almost naked bottom at him. At this he seemed to lose control and the real Alan revealed himself, lowering his shorts as he stood up and then pulling mine down before reaching for a tube of lubricant. Meanwhile Jill was reclining with the skirt of her leotard raised as she stroked her blatantly moist crotch and whispered, “Go on, Alan, fuck him, fuck him deep!”

I then felt the very moist tip of Alan’s cock touch my puckered rosette and gently push. I pushed back and in a moment my sphincter yielded and his penis slid very deeply inside me before he started a regular fucking motion. Jill was getting very excited at watching her brother fucking another man’s arse and very soon she whispered, “Oh God”, and then uttered a yell of pleasure as she climaxed. Her interest in our activity was still strong, however, and she came over to us, positioned herself so that her mouth could accommodate my penis which she started sucking avidly, obviously enjoying the flavour of the pre-cum which was oozing from my cock. The sight of his sister orally servicing my penis while he was deep inside my arse stimulated Alan even more and he quickened his pace as he felt his spunk rising and it was a thrilling two minutes before his cock exploded inside me as his balls pumped their voluminous contents deep inside my rectum. I orgasmed almost simultaneously and Jill gratefully accepted my entire load in her mouth, obviously enjoying the taste of my semen as she rolled her tongue around her mouth before gratefully swallowing my gift. But she wasn’t satisfied and no sooner had Alan’s now limp cock slipped out of me than I felt her lips and tongue on my anus then a brief break as she told me to push it out. It was obvious that she wanted to drink her brother’s semen too so I obliged and using my rectal muscles I squeezed Alan’s cum out through my anus where it was lapped up by Jill whose tongue continued to give me great pleasure as she did her best to get it inside me so as not to waste a drop of her brother’s semen. It was another 5 minutes before her tongue and my anus parted company and then it was because another part of her anatomy was demanding attention. I had noticed a potty near the sofa when I arrived and wondered why it was there; it now became apparent that it was in case of urgent need which Jill was now experiencing for she dashed to the potty and sat on it without removing her leotard and with a loud gushing sound just emptied her bladder through her already very moist gusset. I too was experiencing a full bladder and asked where the lavatory was. Jill checked that my need was purely urinary before asking me to empty my bladder down inside the front of her leotard which she was pulling clear of her chest revealing a tempting view of her beautiful bounteous breasts which I then proceeded to soak with my piss as I emptied myself as instructed. My piss ran down over her breasts, belly and cunt before joining hers in the potty. I was about to shake off the last drops when I again felt Jill’s mouth around my manhood as she sucked me clean. It was apparent that she enjoyed the taste - and feel - of urine as well as semen which she then confirmed by standing up and drinking our mixed piss from the potty before handing it to Alan who also enjoyed a fresh warm drink.

By now I was blatantly hard again after watching this and I positioned myself behind Alan while Jill passed the lube tube to me. I coated my cock and the inside of Alan’s anus with lube using my fingers before attempting entry which I accomplished with ease thanks to Alan’s assistance and this time it was my turn to pump spunk into a welcoming rectum. He was delightfully tight as he squeezed his anal muscles around my thrusting cock and the inside of his rectum felt lovely and warm as I proceeded to fuck him with enthusiasm. He pushed back with every one of my forward thrusts as he wanted me deep inside him. My arousal was such that it wasn’t long before I was pumping my spunk, filling him with my love cream. My cock softened and slipped out only to have Jill’s mouth engulfing it once more. After ensuring I was clean and not a drop of semen remained to be sucked out, Jill then applied her mouth to Alan’s anus and sucked the rest of my semen out of him as he squeezed it through his anus and into her mouth. We were all well satisfied and I joined Jill on the plastic covered sofa while Alan made coffee for the three of us. I’ve been invited to visit again and next time I shall wear some of my feminine finery and see what their reactions will be. I’m looking forward to next time.

I was exploring various websites looking for an intimate friend when I came across an advert that really grabbed my attention:

Young gay male seeks live-in position with older gay male. I shall perform household duties such as cooking, laundry and miscellaneous chores in exchange for accommodation and food. I shall dress as my employer instructs me in anything from French Maid to Schoolgirl to rubber, leather or lycra outfits, even adult baby wear as I have a special interest in watersports and similar nappy activities. I shall also assist my employer in any intimate activities he may wish to perform with me. He will be a lover of feminine attire although not necessarily full time and an interest in watersports will be essential. Please click the reply button if you’re interested.

I have been a part time transvestite for all of my adult life and I discovered the joys of watersports before I bought my first pair of women’s knickers so the advertiser seemed a perfect match and to have someone to cook my meals and wash my smalls would be very welcome so I clicked the reply button and wrote:

Dear advertiser, you seem like my dream “gentleman’s gentleman” to use an old-fashioned phrase. I am a gay part time transvestite with a love of very sissy outfits and I do tend to have “accidents” in my underwear or nappies. I do tend to wear nappies if I’m planning an “accident” but sometimes the mood takes me and I just do it in my underwear which adds a certain thrill. I would also be interested in other intimate activities such as receiving a urine donation directly into my rectum or relieving my full bladder into your mouth, rectum or just into your undies/nappy. I am in my early 60s, slim with no tattoos or piercings and very little body hair. I shave my genital, pubic and anal areas regularly. I have a four bedroomed detached house in a secluded lane with a good sized garden for outdoor fun when the weather is warm. I hope this sounds right for you; please reply anyway letting me know your opinion to *******@*****.***. I look forward to hearing from you.

He replied that my situation sounded just right for him and we arranged for him to visit me for an interview. I instructed him to come dressed as a maid but wearing a nappy under his skirt as I wanted to see how feminine he could make himself. The appointed date and time arrived and I answered a ring at the door to see a very sexy very feminine person on the doorstep so I invited her in, thinking that she was sufficiently feminine to pass as a genuine maid should I have friends or family visiting. This was a real bonus as I didn’t want to confine her to her room when friends came round. I showed her into the lounge where I asked her to do a twirl; she obligingly spun round, her short skirt lifting enough to give me a glimpse of a large pair of pink satin frilly knickers which I assumed were covering her nappy. I told her to lift her skirt and lower her knickers to verify that she was wearing a nappy; she obeyed and under her delightfully sissy nappy cover knickers she was wearing a very large terry nappy folded to fit her extremely well with multiple layers of terry towelling for maximum absorbency. We had a chat and I made coffee for both of us, a task which I explained would become her responsibility should we agree that she would become my maid. After an extended conversation I told her that I had a full bladder and that I would like to empty it into her mouth. I explained that I would release short spurts to give her time to swallow so that she could avoid letting any of my pee go anywhere other than down her throat. I instructed her to pull down my girly shorts and knickers and kneel in front of me with my penis in her mouth and her lips tight around it. She obeyed and once my semi-tumescent cock was in her mouth I released a spurt which she obligingly swallowed. Further spurts followed until my bladder was completely empty and not a drop had been spilt. She told me how she had enjoyed being used as a toilet and would it be ok for her to empty her bladder into her nappy. I agreed with enthusiasm, pleased that she had instantly learned from my earlier instruction that she had to get my permission for every personal bodily function that she needed to perform.

A tour of the house followed during which I showed her to her room but explained that if we continued to get on together as well as we were doing that day, she would be expected to share my bed which I explained was well protected against wetting accidents during the night; I usually awoke during the night and didn’t enjoy getting out of bed to use the toilet so I usually just did it in the bed, changing the wet bedding in the morning. I asked her if that would suit her and whether she would also wet the bed to which she enthusiastically replied with “Oh yes, very much so!” I felt that I had tested her pretty thoroughly but there were two more intimate activities I wanted to test her with. For the first I removed my shorts and knickers and told her to remove her nappy and nappy knickers and slide her cock deep into my rectum with the aid of some lube I gave her. I was delighted to see that she was already very hard as she removed her wet nappy so I got on the bed on all fours and told her to fuck my arse. She had a thick uncut cock about 15cm long with the foreskin not quite long enough to completely cover the head - in other words the perfect foreskin length. She lubed her cock and slid a well oiled finger into me before I felt her cock tip touch my anus as it started its probing, pushing gently so I pushed back and then she was in, my sphincter yielding completely as she began a regular thrusting, fucking me in a very exciting yet comfortable way. After about 5 minutes she yelled, “Oh God I’m coming!” followed by a series of grunts as she pumped several large spurts of her love juice into me. I had avoided an orgasm but was very ready to return the favour so we swapped places and it was now my cock that was fucking her arsehole. This time I lost control after only about 2 minutes but the intensity of my orgasm was tremendous as I emptied my balls into this delightful new friend I had just met.

We had got on so well that I told her there and then that I would be very happy to have her live with me as requested in her advert and that I would particularly enjoy having a regular sex partner living with me and did she want to accept my offer. Her reply was very positive so the only thing remaining was to arrange a date when she could move in. I told her that I’d like her to dress as a woman most of the time but especially when I had friends round and that she wasn’t to mention to anyone that she was really a man under her feminine finery. She accepted my conditions with enthusiasm and she’s moving in next week!

Another instalment will follow so watch this space!

I had an eye test booked and duly turned up for my appointment dressed casually in white shorts (over pink panties), pink teeshirt, white ankle socks and trainers. My turn came and I was ushered in to a dimly lit room by a rather dishy young man who turned out to be the optometrist. During the test he made the occasional casual remark in response to which I revealed how much I liked going for walks around the various parks, lakes and rivers in the town. He asked if I had a favourite spot so I mentioned a riverside area well known for cruising. He added that it was one of his favourite spots and that he often went there on Saturday mornings.
I decided to go there myself next Saturday morning and see if he turned up. I was pleasantly surprised to see him strolling by the river dressed in yellow thigh length lycra shorts and a figure-hugging white lycra teeshirt, both of which did nothing to conceal his physique. I too was wearing lycra, maroon thigh length shorts and a pink long sleeved top. I greeted him and we shook hands. He commented on how well my shorts suited me so I returned the compliment, adding that his shorts also suited his endowment which by now was semi-hard and making a very noticeable bulge in his shorts. I walked over to some exercise bars and bent over, flaunting my buttocks at Brian, the optometrist. His bulge was getting bigger and so I returned to his side and without thinking I put my hand on his bulge and said,
"I think we need to do something about this! Your place or mine?"
"Mine, so I can also show you my favourite outfits, movies, toys, etc.", was his reply.
This sounded like fun so I accompanied Brian to his car; I had walked to the riverside park. It was a 5 minute drive during which Brian told me he was desperate for a pee so I told him I'd like to feel him do it over me through his shorts. I was watching his bulge as I said this and was delighted to see it grow and twitch as he took in my suggestion. However I was even more thrilled when he told me that he'd rather do it inside me. It wasn't long before we reached his house in a secluded location and we headed straight for the bedroom where I got on the bed on my back with my buttocks on the edge of the bed. As I hurriedly pulled my shorts off and raised my legs in the air to expose my inviting love hole, Brian was pulling down his shorts to free his rigid thick 8 inch cock which was obviously ready for action. He grabbed a tube of lube from a bedside table before applying the gel liberally to my arse and his cock before the moment I had been waiting for arrived. The tip of his glans touched my sensitive rosette followed by a gentle, or should I say "genital", thrusting. I felt my anus yield as he slid his manhood deep inside me as he started fucking me. He took about 5 minutes for his climax to reach its peak which was announced by a really deep thrust and a yell of "Oh yeah!" and several more deep thrusts as he emptied his balls into me. He didn't take long to soften after he came which meant he was able to relieve his bladder pressure while still fully inside me. I felt a gradually increasing pressure in my rectum as he transferred his bladder contents into my arse, coupled with an increasingly urgent need to "go". When he'd finished I felt his long soft member slowly slide out of me at which point he said "Let's get into bed!"
I explained that I was now the desperate one but he calmly reassured me that it was ok as the mattress was protected by a waterproof cover and everything else was washable. So we got into bed together and snuggled up in the spoons position with his cock nestling between my bum cheeks. My desperation was not getting any less as he told me to just let it happen. It was delightfully warm and cosy with our bodies in intimate contact and as I relaxed I felt my anus relax too and a warm gush of Brian's pee and cum squirted from my hole with a noisy liquid fart sound, shortly accompanied by a long "Aaahhhhh" from Brian as his cock took the brunt of the deluge. It was very comforting lying together in the warm wet bed and I could feel Brian getting hard again and then for the second time that afternoon I felt him enter me but this time after sliding as far in as he could he just lay still as I enjoyed the well filled feeling in my rectum and the well stretched feeling in my anus. We drifted off to sleep in this position and I had a dream of being constipated with a large solid turd stuck part in and part out. I was awoken by the friction of Brian's cock fucking me again. I had no idea of the time and he fucked me for much longer than before until once again he came inside me before softening and slipping out. The bed was cold by this time so I turned over to face Brian and emptied my bladder over his belly, cock and balls, restoring the warmth to the wet bedding. "We must do this again" were Brian's words as he lifted the duvet and got out.
He lent me a dry pair of shorts and a teeshirt almost identical to mine before he took me home after we'd shared a shower and a coffee. Definitely a friend for life, Brian.

It was the second Saturday of the month, the date of the next local LGBT club meeting. I was nervous as this would be my first visit and decided to go dressed but not too blatantly feminine. I put on a black lacy underwired bra into which I slipped my smallest falsies and over which I pulled a pink sleeveless lycra top. My boobs were clearly discernable but under an outer jacket wouldn't be too noticeable. I chose a white lightweight zippered jacket. On my lower half I wore a pair of open body tights in a light tan shade, a pair of pink lacy panties with a rear access cut out trimmed with lace over which I wore a mid-thigh length pair of very lightweight semi-see-through white shorts. I put on a pair of calf length white socks over my tights and a pair of flat dark unisex shoes. I'm over 6 feet tall and heels do not enhance what femininity I possess. I didn't use a wig or makeup and wasn't too blatantly feminine but I knew that if I bent over, the outline of my panties would be visible through the seat of my shorts. I drove to the club, parked the car and with trepidation entered the club. A transvestite on the door said,
"Ten pounds please. Have you anything you'd like to leave in the cloakroom?"
I paid the entrance fee, declined the cloakroom offer and went to the bar. As I lowered myself onto a bar stool, a very feminine TV on an adjacent stool said,
"Hello. I've not seen you here before",
as she looked me up and down. I unzipped my jacket revealing my modest breast bulges before replying,
"Probably because I've never been here before".
"This is only my second time", she said as she moved her stool a little closer to mine. Her next remark took me aback,
"How do you get four gay guys on a bar stool?"
"Turn it upside down", I replied and added, "but I'd prefer to sit on something just slightly less hard with a nicely rounded end made for easy entry and preferably attached to a man at the other end".
While I'd been talking, Linda (she told me her name later) was fiddling under her skirt and manoeuvring her stool even closer to mine before lifting up her skirt to reveal a magnificent cock, uncut with the foreskin just covering the glans, thick, long and tumescent although not fully erect.
"Like this?", she enquired.
I didn't reply, instead moving my hand until it held that superb example of manhood which stiffened as I touched and gently carressed it.
"They've got some private rooms upstairs, dear, if you fancy a bit of intimate fun", was her response so I picked up my handbag from the bar and followed her. She did her best to hide her semi-erect penis which was tenting the front of her skirt as we crossed the lounge and climbed the stairs to the upper floor where there was a board of hooks with keys hanging from most of them and a notice requesting return of the keys after use and a suggestion that a gratuity be left for the maid on leaving the room. Linda picked a key and led the way down a corridor to room 24, unlocked the door, guided me in and then relocked the door.
"So you liked what you had in your hand?"
she said as she slowly removed her wrapover gym skirt revealing white frilly open crotch panties and an unrestricted view of her gorgeous cock which was swelling as I watched. I really wanted to feel that beatiful piece of flesh sliding deep inside me so I hurriedly removed my shorts and knelt on the bed. Lynda had come fully prepared and applied some lube from a dispenser in her handbag to both my anus and her cock before approaching my arse with that superb cock leading the way and homing in on my love hole. It was an indescribable thrill as i felt her tip touch my puckered rosette followed by both of us pushing gently until with an "Oooh" of astonishment at my ability to accept her thickness, my sphincter yielded and she slowly pushed all the way in until her pubes were against my buttocks. She held still for half a minute to let me get accustomed to the intruder before she began a slow stimulating piston action, very gradually increasing the tempo until after about 10 delightful minutes she started fucking me in earnest and I knew that she was about to shoot her load.
"Cum inside me, please!" I yelled. "Fill me with your love cream!",
I encouraged her and a few seconds later she gave three rapid deep thrusts as she pumped the contents of her balls deep inside my rectum with a long satisfied, "Aaaaahhh".
"Stay inside me!" I begged before she had time to pull out.
"But I badly need a pee; I always do after I've cum."
"Well do it inside me then!" was my response and I waited.
A moment later I felt pressure building in my rectum and knew that Linda was fulfilling my request. As the pressure built, the need to "go" got stronger and stronger and just before it reached the point where I would have lost control, the increase stopped and I felt that long, now soft sausage of flesh slowly sliding out of me as she gently pulled out. I had been optimistic when packing my handbag with essentials and had included a pair of incontinence knickers which I was now needing as I didn't know how much longer I could contain the liquid load filling me. I made it to my handbag and put on the absorbent waterproof knickers before any leakage occurred, but once my sphincter started to leak it relaxed in no uncertain fashion and I felt and heard a noisy liquid expulsion which the knickers absorbed nicely. I felt happy, relaxed and well satisfied as I joined Linda on the sofa for a post-coital kiss and cuddle. This would not be my last visit to the club.

I was on one of my favourite country walks dressed as usual in a feminine top, bra (without padding or falsies), feminine shorts, women's panties and girls' calf length white socks; my only male things were my shoes. However, none of my feminine outer cothes were blatantly feminine, but any observant walker would have been able to tell that I was a TV.
About 200 metres into the walk I noticed a brand new gate on my left and an equally new path leading off into the distance so I decided to explore. After another 300 metres I came across a brand new bird hide, a completely closed wooden structure with a door on the path side and, as I discovered when I entered, openable shutters facing a large water covered area in this new nature reserve. I sat down on one of the benches, opened a shutter and looked for any signs of wildlife.
A couple of minutes later the door opened and a young man dressed in a sleeveless top and short running shorts entered and sat down on the bench next to me. It wasn't long before I felt his hand caressing my thigh and to show my willingness I moved a little closer to him and spread my legs wider apart. My panties that day were french knickers with wide legs so my new friend was able to slide his hand right inside my panties and caress my now tumescent cock. As he was stroking me to full erection he explained that he'd seen me on previous occasions and wondered how he could approach me; he'd also followed me on earlier walks but hadn't had the courage or the opportunity to make a move. Today he'd seen me enter the bird hide and, as no-one else was in sight, he'd taken a chance and made his move, much to my delight.
By the time he'd finished telling me this he'd extracted my cock from the confines of panties and shorts and applied his mouth to my bell end. He was quite an expert with his lips, tongue and teeth and my excitement was rising but before I got too excited he eased off, repositioned himself kneeling on the bench with his back to me and begged me to pull down his shorts and fuck him. I lowered his shorts revealing a black jockstrap and a totally accessible anus into which I eased my rampant cock.
He was tightly closed initially but as i gently pushed and rubbed my oozing glans around his arsehole he pushed back and then the moment came when he yielded to the intruder and I was able to slide in all the way up to my balls which slapped against his with every thrust as I fucked him with enthusiasm, all thoughts of a possible interruption by a third person gone from my head. That time there was no interruption and after a very good ten minutes fucking I reached the point of no return and two strokes later I was pumping the contents of my balls deep inside him. After I'd shot my load I stayed inside him until my cock softened and slid out with a gentle "plop". He had also cum and soaked the front of his jockstrap which he removed, cleaned himself up with a tissue and put his shorts back on. We exchanged phone numbers and names before parting because we planned another visit to that bird hide which had proved so conveniently private.

A few days after Jenny’s revelation of her enjoyment of wetting fun and wearing men’s underwear, she popped round and asked if I was free to go for a walk. Despite the forecast being fine and the sun shining from a cloudless sky, she said it might turn out wet, so I figured that she wasn’t referring to the weather! Jenny was wearing a pink lycra top which showed off her endowment to advantage, and black soft cotton and lycra leggings, through which I could just make out that she was wearing the Jockey Midways figure hugging men’s trunks she had been wearing on “revelation day”. I decided to wear the cotton school knickers I had worn that day under a pair of black running tights, the nearest I could get to Jenny’s leggings without being blatantly feminine. It wasn’t far to the nearest park and as I had recently had plenty to drink, I was almost desperate for relief by the time we reached the park. Jenny too was showing signs of needing relief so we stopped at the first seat we came to - just a flat bench seat with neither back nor arms, which made it ideal for our requirements. I sat down and then Jenny climbed astride me but facing me with our crotches almost intimately close. She had just settled into a comfortable position when I felt a warm wetness flooding my groin, although I hadn’t yet given way to my needs. Sure enough, Jenny was relieving herself through her underpants and leggings and soaking me in the process. After checking that I still had a full bladder she led the way up a narrow path to a secluded wooded part of the park where she crouched down in front of me facing away from me, pulled the waistbands of her pants and leggings clear of her spine and asked me to use her buttock cleavage as my urinal. I was tumescent by this time but not too stiff to pee so I pulled down the fronts of my leggings and knickers and aimed at the base of Jenny’s spine before I opened the floodgates.
“Oooh, that’s lovely!” she exclaimed as she felt my hot stream hit her naked flesh and pour down between her buttocks wetting her anus on its way down to her already sopping crotch. I kept the flow going for a remarkably long time as my bladder had been near to bursting point so Jenny had an extended pleasure before the flow became a dribble then a few drops and finally stopped. We both made ourselves presentable before returning to the main path through the park and then home after a leisurely but, as predicted, wet walk. Jenny suggested we could shower together at her house so after pooping into my place for some dry clothes, I joined Jenny in her shower. The only things she removed before getting into the shower were her shoes so I did likewise and after a long warm wet hug, we stripped off, soaped, rinsed and dried ourselves before putting on dry things.
Jenny’s dry “panties” were a white jockstrap while I wore a pair of frilly pink open crotch panties. We were therefore able to participate in intimate fun without needing to undress as Jenny has expressed a strong desire to be treated as a gay man and receive my stiff cock “up my back passage” as she so coyly put it. So that’s where I put it! After her request, I rapidly became hard and with the aid of a dribble of pre-cum for lubrication, I pushed at her anus until it yielded with an “Ooooh, that feels so good” from Jenny. A regular fucking then began with Jenny clenching her sphincter from time to time as I repeatedly slid all the way in and almost all the way out. She was rhythmically pushing back in time with my thrusts and it was a beautiful sight to see my thick manhood sliding in and out of her gorgeous arsehole between two wide well rounded womanly buttocks.
All good things come to an end but I managed over twenty minutes of enjoyable thrusting before the cum came to my end in a fantastic climax as I felt spurt after spurt after spurt pulse through my cock deep into Jenny’s rectum. She didn’t want to lose my donation earlier than necessary so she put on a pair of incontinence knickers in case she leaked, before making coffee for us both. As we drank and chatted I heard a wet fart sound from inside Jenny’s knickers so I knew that she was still enjoying my gift! Before I left we agreed that we’d do it again, and again and again and again as long as we remained neighbours. I was very much in agreement with this as Jenny was the first woman I’d fucked up the arse and I’d found it very very enjoyable and it was great knowing that she felt the same way too. I returned home well satisfied and looking forward to similar activity in the future,

New Teacher at Trevelyan

After leaving the Trevelyan Academy for Young Ladies, I trained as a teacher with a view to returning to Trevelyan where I had been very happy as a girly boy and as a young lady boy, not forgetting the wonderful sexual experiences to which I had been introduced by both the other girly boys and later on, the teachers. So I applied for a post as maths teacher and got it; having been a student there was definitely a point in my favour. I was allocated a double room in the staff block for an overnight stay after the interview and Julia, the head teacher, had made it clear at the interview that she and her deputy (both ladyboys) would like to get to know me socially that evening. I was wearing a white satin blouse over my pink lacy bra and a short navy blue flared skirt over my lycra control panties to keep my manhood in check. My legs were clad in black nylon stockings with lacy tops held up by a black satin suspender belt under my panties.
The staff common room had a bar, a television set and various other leisure facilities and it was here that we met in the evening after dinner. I was told that I was the guest and would not be expected to pay for anything. Amy, the deputy, fetched the first round of drinks and as we chatted I felt another nylon clad thigh caressing mine - the head obviously wanted to get to know me a little better so I responded in like manner but I also used my hand to explore under her skirt where I encountered a soft silky pair of satin panties with a very noticeable bulge at the front. This I caressed gently and it swelled considerably at my touch.
"I can see that we're going to get on very well together, my dear", were Julia's next words as she shifted in her seat to get a little more comfortable. As the evening wore on and we became less inhibited as a result of the drinks, my thighs, genitals and buttocks were receiving strokes and caresses from both Julia and Amy. At about 10 pm Julia suggested that she and Amy could show me to my room as I'd had a long day. I had been told that there were hot drink facilities and snacks in the room so I invited them both in for coffee. They accepted and Julia insisted on making coffee. Amy went to the toilet and when she returned was wearing only her sexy underwear. Julia explained that Amy did what she was told and would be willing to provide me with anything I wanted, an overnight companion to share my bed being her initial suggestion. Julia then added that she would like to slide her cock deep inside my arse. As Julia was speaking, Amy was undressing her and I gasped with delight when I saw the size of Julia's penis. However I felt that it might be a little too large for comfort so I asked if Amy could fuck me first. "But of course, my dear", was Julia's reply and as she pulled down my panties, Amy produced a tube of lube which she proceeded to apply to my anus and her penis which was now rigid but a more comfortable size than that of her mistress. I got on the bed on all fours and immediately I felt a moist helmet probing my puckered rosette. I pushed back as I felt Amy thrusting and only a few seconds later I felt my anus yield as Amy slid all the way in. After about 5 minutes of Amy's thrusting I felt her increase the tempo and depths of her thrusts and suddenly she yelled "I'm coming, oh God I'm coming". She held still with her penis totally inside me but I felt it pulse as her balls pumped their contents deep inside my rectum. A minute later and her flaccid penis slid out with a gentle plop but I had only a moment to recover before Julia had pushed Amy to one side and was lining her penis up with my hole. This time I knew I could accept her long thick shaft as Amy had loosened me up nicely but it was still a stretch as I opened up even wider as Julia pushed her cock all the way in. I felt wonderfully full and then Julia started thrusting. Another most enjoyable ten minutes went by before Julia needed release and again I felt the increased tempo as her thrusts became faster and deeper until with a long "Aaaaaaaah" Julia emptied her balls into me and shortly after for the second time that evening I felt a flaccid cock slip out. Julia then ordered Amy to rim me and to swallow any spunk that emerged. She also told me to push the sperm out so that Amy would have plenty to drink. I pushed and felt liquid oozing out then a liquid fart and another load emerged. Amy was a good girl and swallowed the lot but continued to use her tongue on my anus to ensure that I was both clean and well satisfied. I was already feeling 'at home' and I looked forward to a long period of residence at Trevelyan.

I'd been out for a walk in local woods, during which I had needed bladder relief. I had been wearing black joggers at the time over my maroon cotton interlock school knickers so I'd decided to just let my pee flood my knickers etc. as the wetness wouldn't be visible on the black joggers. On getting home, I removed my shoes and joggers as I didn't want to drip pee throughout the house and then the door bell rang. My automatic reaction to the bell - opening the front door - took me by surprise and I found myself standing at my open front door in teeshirt and obviously wet girls' school knickers facing Jennifer, my next door neighbour! She apologised for calling at an inconvenient moment as she handed me a large parcel she'd taken in for me as I'd been out when the postman called. I thanked her, took the parcel (a large pack of disposable nappies) and shut the door, realising that I'd just revealed to my neighbour my interests in female underwear and wetting. I was wondering how I could prevent this information being spread around the neighbourhood when the phone rang. It was Jennifer and she suggested that I pop round for a cup of coffee and a chat in half an hour. I wondered what she had in mind; she was a kind, friendly single woman a few years older than me and I didn't think she had any malicious intent. I like to have a leisurely shower and half an hour was cutting things a bit fine so I put on a disposable nappy after using some wet wipes to clean mysef up. Over the nappy I put on a pair of navy joggers and checked my appearance in the mirror. I don't often resort to alcohol to give me extra courage - or should I say "couldn't-care-less-ness" - but this time I downed a can of beer followed by a large whisky chaser as I was very apprehensive about the imminent meeting with Jennifer.
The half hour was over in a flash and I found myself ringing Jennifer's door bell. She welcomed me in with a smile and a hug - her usual greeting - and led the way to her patio where two large mugs of coffee stood on a table. As we sat down Jennifer told me that she hadn't intended to intrude on me at what seemed to be a private moment and that what she'd seen would remain confidential. I thanked her and the conversation drifted into neighbourly small talk. I was just finishing my coffee when I noticed a spreading puddle under Jennifer's chair yet she seemed completely relaxed. Was it possible that we shared a love of watersports? I couldn't think of any other reason why she was so blatantly wetting herself so soon after catching me in a similar situation. As she noticed the direction of my gaze, Jennifer explained that she too enjoyed wetting herself and as she was speaking she got up from her chair and lifted her skirt to show me her well soaked Jockey Midways thigh length male underpants. This was wonderful: we both enjoyed both wetting and wearing underwear designed for the opposite sex. As I watched her flaunting her soaked undies, another spurt forced it's way through the cotton underpants.
Jennifer then asked me to show her my underwear; I now wished that I was wearing a pair of sexy feminine panties but I stood up and lowered my joggers to reveal my adult nappy.
"Oh, you wear nappies too! How wonderful! Are you wet now or are you going to be naughty and wet your nappy just for me?" were Jennifer's words as she saw my nappy . The beer and coffee had ensured a full bladder and in response to her comment I started to pee. The front of the nappy turned darker as it absorbed the pee so Jennifer could see that I was doing a wee-wee in my nappy. She hugged and kissed me and then she undid the sticky tabs holding my nappy in place, got down on her knees and took my pee soaked cock in her mouth after begging me to do some more pee in her mouth. I did my best and managed a further few spurts and a trickle, all of which she eagerly swallowed. By now my manhood had become enlarged and her continued sucking was arousing me to the point of orgasm. I didn't hesitate to discharge my load of semen in her mouth as by now I was sure that that was what she wanted. She kept sucking and swallowing until she had drained the last drops from my now flaccid penis. After I had slipped out of her warm wet welcoming mouth she expressed her enthusiasm for another session in the near future. I agreed and it was in a happy and lighthearted mood that I returned home. I wondered what other delights we'd be sharing in the future.

I was out walking in a local park when I saw, coming towards me, a most interesting looking person in tight light grey leggings and a figure-hugging pink lycra top. I say "interesting" because there was a very noticeable bulge in the leggings at the crotch and also two equally obvious bulges at chest level with the nipples clearly outlined. I wanted to get to know "her" and I hoped that she'd be interested in me, a gay transvestite male. As we approached to within talking distance, I said,
"Good afternoon. Do you have the time?"
I ought to mention that my clothes at the time comprised a silky blouse, not frilly or lacy but fastening the women's way, and a pair of women's shorts, not blatantly feminine but pleated in a way only found on feminine shorts and trousers. Underneath, my undies were all feminine - a lacy cotton chemise and a pair of tight black lacy panties with frills across my buttocks. I was also wearing trainers and white socks.
Her reply was most encouraging,
"I do. Do you have the inclination?"
I replied in the affirmative and joined her walking back in the direction from which I had come. Our conversation revealed that she had noticed my feminine blouse and shorts and had thought that I might be an interesting person to know. By the time we reached the car park we were on first name terms; I had revealed my sexual orientation and interests, in particular a desire to get to know a transexual who had breasts and lived as a woman but had no intention of changing her masculine genitals. She, in return, had told me that she was single and looking for a boyfriend who would accept her as she was and would be willing to take both sexual roles, giver and receiver.
She invited me back to her house and led the way in her car. When we arrived I was pleasantly surprised to find that she lived only a couple of streets away from my home. As she welcomed me into her lounge I noticed a dark wet spot on the front of her leggings where she had leaked a little pre-cum. I commented and after mentioning that her knickers and leggings would have to go in the wash she told me to follow her to the bathroom where, after removing her shoes, she stepped into the bath, turned to face me and her small wet spot became an ever-growing dark area as she deliberately wet herself, flooding her knickers and leggings with the contents of her bladder. By now my cock was rigid and tenting the front of my shorts which were also showing a small damp spot. As my new friend lowered her now sodden leggings and knickers, she bent over, turning her back to me and telling me there was some lube in the small cupboard with the mirror door over the wash basin. I hurriedly lowered my shorts and knickers, found the lube and applied some to her anus and some to my cock. A moment later I was pushing at her sphincter and suddenly as she pushed back I felt her anus yield and I slipped all the way in, my balls slapping against hers as I started fucking her in earnest. I did my best to hold back and managed to last just over five minutes before I felt my spunk rising and the increased sensitivity of my cock which heralds an imminent orgasm. I thrust deeply into her as far as I could as I felt my cock spasm as I orgasmed and shot a huge volume of semen deep inside my new friend. I didn't want to pull out but inevitably my cock softened and slipped out with a soft plop followed by a dribble of spunk. Julie asked me to photograph her anus with the blob of semen still visible. She told me where to find her camera and, after pulling up my knickers and shorts, I took several shots as, once she'd heard the first click, she started pushing out more of my semen, so she ended up with about a dozen pictures of her anus in various stages of discharging my gift of love juice. She then pulled up her wet knickers and leggings and, after fetching a waterproof plastic sheet from her bedroom, she covered the sofa in the lounge with it and invited me to sit down next to her. I always have a need to pee after an orgasm and I mentioned this to Julie who told me to just do it in my knickers as I was sitting there. I followed her suggestion and thoroughly enjoyed the warm flood over my belly, cock and balls as my bladder emptied.
It had been a deightful way to begin a new friendship and I was sure we'd have many more wet and messy intimate sessions in the weeks to come. I'm looking forward to receiving her love juice up my mancunt next time!