A Good Relationship Ch. 6

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Transvestite meets new man.
5k words
4.21
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Part 6 of the 7 part series

Updated 10/31/2022
Created 11/02/2000
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Ian H.
Ian H.
6 Followers

The next weekend, Howard decided we would go for a drive. I was at his house, and he said he would like to go for a drive and stop some where for a picnic. He went upstairs for a while. When he came down he had some clothes over his arm, he said he would like me to wear them. He said he was going to get a picnic hamper packed and left the room.

I undressed, I had shaved off my body hair that morning, and started to dress in the clothes Howard had picked out, first a very well padded white bra, lacy white suspender belt, white stockings, white frilly panties, pink little girl style party dress which fitted up under my padded bra then flared out from there, then a pair of white high heels, then a blonde wig with pig tales. I looked like a little girl going to a birthday party. Howard came back into the room carrying a hamper, looked me up and down, he said all I needed was some red lipstick, so I went and put some on. Howard put the hamper in the car, we both got in and we set off, it was a bit cloudy but nice and warm as we drove along almost deserted country roads.

We reached a main road and turned to the north, it wasn't far to Scotland, we passed a few lorries on a steep hill, then the road went into a forest, a sign said "picnic area & toilets", Howard pulled in. We drove passed the toilets, which was an old bungalow type building, to an area with set out tables and benches with a big grassy area all around. Howard parked the car and he picked up the hamper and said we would have the table over the back near the edge of the forest were the grassy area ended. Only one other table was in use when we got there, a couple were sat drinking tea from a flask, they hardly noticed us as we reached our table and sat down. Howard unpacked the hamper and poured some tea for us both, it had been a while since breakfast, it was 1:30 in the afternoon now. We tucked into some sandwiches and buns that he had made, we were both hungry.

The couple had finished, packed up and left, a lorry had pulled up a scruffy man thick set with a big black beard jumped out of his cab and looked at us then walked off in the direction of the toilets, glancing back at us a couple of times. We continued our picnic, the lorry driver came back and lay out on the grass near his truck. Another truck pulled in a while later as we were packing up, Howard put the hamper back in the car, he said he was going to the toilet before starting back, I said I would go as well.

I was in a bit of a dilemma as to which toilet to use, as there was no one near I followed Howard into the men's. He went to one of the urinals, I went to the far end into a cubicle, the place was not very well lit. a couple of bulbs were missing, but the sun shining through the windows helped to light the place. I lifted my dress and pulled down my panties and sat on the toilet seat, I was soon reading some of the messages and looking at the drawings on the door and walls. These toilets. it would seem was used as a meeting place for people for all types of sexual activities. I finished using the toilet pulled up my panties and re-arranged my dress, I flushed the toilet and unbolted the door and walked out of the cubicle, Howard wasn't there, I assumed he had gone back to the car.

I was part way towards the door when in came the big bearded lorry driver with another man, probably from the other truck that pulled up. I went to walk round them but the big man grabbed me by the arm. Not so fast he said as he pulled me towards the far end. He said he would like to now what I was doing in the mens toilet, he opened the cubicle at the far end, he pulled me in behind him then he shut and bolted the door. There wasn't much room in there he pushed me up against the bolted door, he was much taller and heavier than me, he took my head in his hands and turned my face towards him his mouth pressed against mine he forced his tongue between my lips and it shot deep into my mouth, flicking over my teeth then probing down my throat. I felt him tugging my dress up and a hand was soon squeezing my balls and cock through my panties. The other man was banging on the door asking what was happening.

He removed his mouth from mine to tell the other man to shut up he could have his turn next, he then shoved his hand down the front of my panties and grabbed hold of my cock and began roughly wanking it, unfortunately it began to respond to him and was soon hardening up. He went back to kissing me some more, his tongue down my throat again, with his free hand he undid his trousers and they fell to the floor, he then pushed his underpants down ha took my hand and placed it on his cock, it was rigid already. He then placed his hands on my head and began pushing downwards I was soon kneeling on the floor his cock just inches from my face. He took great delight in rubbing it all around my face before finally shoving it to my lips and pushing hard he forced my lips open and then on inside, it was soon crammed in as far as it would go, his balls up against my chin, the head was down my throat nearly choking me.

He held my head in his and then began pumping his cock in and out of my mouth, he stopped and pulled me to my feet, I looked up, there was his mate looking over the partition wall from the next cubicle. The man turned me ruond to face the door, he sat down, then reached up under my dress and hooked his fingers into the waist of my panties and tugged them down around my ankles then lifting one foot at a time he took them off and through them up to his mate. He forced me to bend over and spread my legs, he pulled me back towards him, then he began to lick up and down my ass, his rough beard scraping my bum. The tip of his tongue was pushing it's way into my hole, which was then replaced by a finger, his spit was the only lubrication.

After a short while of him fingering me he stood up and pushed me forward, my head was pressed up against the toilet door, his cock was pressing up against the entrance to my hole then with a sudden lunge he was up to the hilt inside me. With the lack of grease his shagging me was a little painful, thankfully it was not long before he emptied his balls inside me. He quickly pulled his cock out and unlocked the door and pushed me out, his mate was waiting his dick already in his hand, he pushed me to my knees and made me suck his cock, then I was made to get on hands and knees and the man knelt behind me and rammed his cock up me, the cum from the last bloke was a good lubricant, at that moment another guy came in from outside and watched for a short time, the man fucking me up the ass.

Then his cock was out and he knelt in front of me and shoved his cock in my mouth, each thrust from the cock up my ass thrust me forward so the cock went deeper into my mouth and down my throat. The guy behind me shot his load of cum up my ass, the other man took his cock out of my mouth and made me lay out on the floor on my back by the urinals, the floor was damp with piss and was soon soaking into the back of my dress. The last bloke took my legs and lifted them up and over on top of me a knee on either side of my head, the first man with the beard knelt down and held my legs there.

The last bloke knelt by my bum and lowered himself down on top of me his cock slipped straight up me to his balls, then he was shagging me long and very deep his balls slapping my ass, his cock making a slurping noise as he thrust in and out. Soon he pulled his cock out just in time to spray my belly, suspenders and my cock and balls with his cum. He stood up his cock still pointing at me, my legs still held firmly, he began to pee, he aimed his piss at my belly and then over my stockinged legs, all the men began to laugh at my plight, I was unable to move as the second man puled out his cock and began to piss on me also. When they had finished they put their cocks away, then the bearded guy finally let go of my legs and I straightened them out and slowly stood up, I noticed Howard standing in the outside door way, how long he had been there and how much he had seen I don't know, another man was there he had been watching.

The three men left the toilet, I walked towards Howard, he looked me up and down, my dress was soaking wet making it see-through and it clung to me I was trying to pull it down to cover myself up, Howard turned and walked outside, I followed, he said there was no way I was getting into his car like that. The piss was dripping from me as we walked, it had mixed with the cum on my belly and was now running down my legs. Howard just got into his car and without another glance drove off, I shouted after him to stop, but he just kept on going and disappeared down the road. I didn't know what to do I was in the middle of nowhere, I was going back to the table we were sat at when a man said to wait, it was the man who had been in the doorway with Howard, he caught up to me and said he had seen what had happened, Howard driving off and leaving me as well, He said his name was Dan and he lived quite near he would take me back there to clean up etc. I accepted his offer.

The man with the black beard went by in his lorry and through my panties out of the window and laughed. Dan picked them up and said there didn't seem any point in putting them on, he put them in his pocket then got an old blanket from the boot rapped it around me and helped me into the passenger seat and put the seatbelt on for me. As we drove along he said he was 61 years old, I commented that he only looked about 45, which was true , he did. He went on to tell me he lived alone and often went to those toilets, to read the writings on the wall and see if he could meet anyone, that was his only sexual excitement. We had gone a few miles when we hit a traffic jam, he said we were very near his house to, he said he wanted me to tell him all about myself and my relationship with the man that abandoned me.

The jam was a long one, I was nearly finished telling him all about the times with Howard, the wedding, the Africans, the horses he kept asking questions and wanting me to go into great detail about what we did, how we did it etc., by the finish he knew everything, he really did seem very interested, he asked me if I enjoyed the dildos and the big cocks up my ass, I nodded in reply. We were moving again, and he told me he found it difficult to get an erection, and that he got most of his enjoyment, from watching, voyeurism, and giving pleasure in any way he could. We pulled up in the road outside his terraced house, he got out and came round and opened the door for me and helped me out then went and opened the front door and we both went inside. He said the first thing was to have a bath while he took my clothes and put them in the washing machine.

He took me to the bath room upstairs and told me to help myself to anything I needed, razor etc., he turned on the taps and told me to get undressed, which I did, he left with all my clothes and my blonde wig. I had a long leisurely bath then shaved all over legs, pubes etc. Dan came back with a dressing gown for me to wear when I had finished. I got out of the bath dried, put on the dressing gown and found Dan in the kitchen, he had made us both a cup of tea, we sat and drank it together then he showed me around his house, the rooms were not big but there was three bedrooms and bathroom upstairs and living room, kitchen and dining room down stairs. He said he had a big basement also, it was his "playroom" and he would show me it another time. He said it was getting late he would show me to my bedroom, we went up stairs, he took me into the single room, he said we would have to think about getting me some clothes, as he took my robe and hung it on the back of the door.

I jumped into bed naked and Dan tucked me in and gave me a long kiss on the lips, then left wishing me a good nights sleep. I slept well woken by Dan coming into the room with my clothes, he said breakfast would be ready soon, he left and I got dressed, all my clothes all spotlessly clean. I put on my wig last then went down to the kitchen, Dan greeted me with another kiss on the lips, I was quite getting used to that by now, he said I looked lovely, the party frock suited me. We sat down and had breakfast, he said he hoped he didn't sound to forward or anything like that, but would I like to stay a while because he enjoyed my company and wanted to get to know me better, and that he would take me home to get some of my things.

I thought about it over breakfast, I was owed some holiday from work and he was a nice man and I needed a change so I told him yes. I used his phone and found out I had two weeks owing me so I took the lot. Later that morning we left the house Dan gave me a long raincoat to put on, it came down to my ankles, just above my white high heels, he fastened it down the front as far as my waist, we went out and got in the car and began the drive to my house. We had not gone far when he reached over and put his hand on my knee and said he hoped I didn't mind but he would like to see my legs, I said that was okay and he parted my raincoat, my dress had ridden up a bit, he could see my stocking tops which pleased him so I left them on show for him. We got to my house, I said I would like him to come in and choose the clothes he would like me to take, he went through my wardrobe and picked out mainly girly things, short skirts, tiny panties etc., he was enjoying going through them.

We didn't stay long and we saw on sign of Howard, I had picked up makeup and toiletries and we loaded the car and went back to Dan's house. It was lunch time when we got back the conversation was getting quite sexy he asked me about dildos he knew I liked them and would I go into town with him after lunch and choose one or two. I said yes of course he was being good to me and I would like to please him. So, after lunch he got me to put on some lipstick, then he helped me on with the raincoat, again he only buttoned it down to my waist, he said he wanted to see the men's faces, as it parted occasionally, and they could see my hot skirt and legs and maybe more.

He said we were going on the bus because parking in town was bad, we walked down to the bus stop, we didn't have to wait long before a bus turned up, there was hardly anyone on board, Dan told me to sit in the side seat just inside the door so every one getting off or on the bus would have to pass me. He said he was really going to enjoy this it was his voyeur thing taking over, I said it sounded fun, he was very pleased that I would do this for him. We got on the bus Dan having paid the fare, I duly sat in the seat as planned, Dan soon made signs for me to push my coat off me knees, I did and it opened out right up to my waist.

A few people got off an on the men were looking at my legs, Dan had a big smile on his face, he then made signs for me to raise my skirt a little and part my legs slightly, I did so showing just a little of my white stocking tops. Dan who was sat directly opposite could see bare thigh in between my legs and a flash of my white panties, he was really enjoying himself and I was too. A middle aged man got on and walked past staring at my legs then turned and walked back and sat next to Dan still staring at the view. Dan winked at me and mouthed the word "more" I smiled back and shifted in my seat making my dress ride up higher, he could now see all of my stocking tops now and a lot of my panties as I opened my legs just a tiny bit more. We soon reached our stop and we had to get off. Dan said he had enjoyed that so much, he loved the expression on the mans face as he sat and stared at the view I was giving him.

We walked a short way and Dan directed us towards a sex shop, the outside looked very plain, but inside was a different thing, everything that had a sexual flavour was here. I spent ages looking round, there was a few men browsing as well, they gave me the occasional glance and the odd stare, it was probably my blonde wig or maybe it was the times when my coat opened to show my short pink dress. Dan beckoned me to him he had found the biggest selection of dildos I had ever imagined, he asked me what size I would like, I picked up one it was about 9 inches long and about 3 inches in diameter, putting my hand round it my index finger and my thumb were nowhere near meeting. It was black and shaped like a cock with a giant head on it, it was rubber and flexible, I got more looks from passers by as I was bending it.

Dan had found another which was a little smaller but had a hose coming out of the base to a blow up bulb, he pumped it a few times and it got really big. So Dan bought those two and we left the shop, we went back to towards the bus stop but he needed to go to the super market for some food. We got a trolley and entered the shop and began going up and down the aisles, we were less than half way round when Dan said we were being followed by the man off the bus. I looked back and saw him pretending not to notice us, but it was definitely him, I said to Dan perhaps he was hoping for another flash, would he like me to give him a good look. Dan had a big grin and nodded enthusiastically, the next aisle was empty I undid all the buttons on my coat, then I reached up behind me and lifted my dress up above my waist at the back then I leaned far over the edge of a freezer pretending to get something from the very bottom and waited for he man to come round the corner.

Dan had positioned himself to watch both me and the voyeur, he came round the corner and saw us and began to walk up towards us, I waited until he was very close and pulled the back of my coat fully round to one side. Both he and Dan had a good view of my undies to above the waist, they could see all of my white suspender belt, my white frilly panties, bare thigh down to the tops of my white stockings. The man stopped and stared making sure he got a very good look, Dan loved it, he was very excited, I stayed like that for a short while until some other people came round the corner into our aisle and I quickly covered myself up, pulling my dress back under my coat. The man went on around the corner, Dan and I finished the shopping and went back to the bus stop still talking about the voyeur. We got on the bus it was very full we had the last couple of seats, so we were unable to get up to any more mischief.

Dan and I got off the bus and went indoors, we sat down and talked about our wonderful day, we had tea then watched a bit of tv then Dan said he would like to show me his basement. He unlocked the door under the stairs and we went down a flight of stairs, he turned on the light, there was two biggish rooms one was a workshop with many tools and gadgets on the wall and the bench. He took me into the other room, it was like a living room with carpet on the floor, a low doctors type couch was across the middle, one end up against the wall, he sat down on it and I sat along side him, the black leather was cold on the backs of my thighs, he turned to me and began kissing me, soon his tongue was probing my mouth, then his hand was sliding up my leg, over my stocking top and up to my panties.

He pushed his hand between my thighs and cupped my balls and was squeezing them gently, then his hand went higher and slid inside the top of my panties then down onto my cock then was slowly wanking it. I responded to his touch and my cock was soon hard, he stood up and gently turned me round so I was lying out my head at the wall end. he reached behind him and picked up a pillow and placed it under my head, then he lifted my dress up over my padded bra. His hands went to my panties, he pushed one back under the waist and was playing with my cock the other was tugging them out from under my bum, I lifted my self a little so he could take my panties down. He was soon sliding them down my legs and right off, he looked down at me then reached under the bed on both sides and brought up some heavy leather straps which he fastened at my waist, I began to ask him what was happening, but he told me to lay back and enjoy, so I did.

Ian H.
Ian H.
6 Followers
12