XP06 1

I'd had lots of girlfriends by the time I was in my late thirties. I'd even married the last one and was sad when she divorced me. It was a fair cop; I'd been shagging my secretary. But she soon tired of my moods after the separation.

An old mate, whom I had kept in touch with since my school days, came over one afternoon for a pint. His wife was away and he was bored. We were pretty pissed when the pub closed and Trevor realized he'd missed the last tube. I said he could stay the night and thought nothing of it when I got into my bed beside him. He was fast asleep and, soon, so was I.

When I woke, it was still dark and Trevor's arm was across me I could feel his cock pressing against my back. It was erect. So was mine. It always is in the mornings, especially after a bellyfull of real ale. I moved his arm and went for a piss. As usual, I had to sit down and bend forward to do it. When I got back into the bedroom, Trevor was awake. He looked at my stiffy, which still jutted out parallel to the floor.

When I got under the covers, he put his arm around me again and took hold of my penis. He just held it lightly. He didn't move his hand at all.

'This cock of yours is very big, Colin.'

I was usually horny in the mornings but I had no thoughts of doing anything with my friend but I rolled over and felt his dick. It was still stiff but very small. I hadn't had much experience of seeing men naked. Not since school; and I'd always thought pricks didn't vary much in size. Not that much anyway. I wondered if he was fully erect and, without thinking, started to rub him to see if he got bigger.

'That's nice,' he said and started wanking me. He pulled me closer and kissed me on the mouth. I didn't like that. His face was bristly and his kiss was quite rough. But my cock liked what he was doing and I lay back as his other hand took hold of my balls gently. I felt his finger between my legs. It started circling my rectum.

'Do you like that?'

'Who doesn't,' I replied.

He was still rubbing my cock and I came over my chest.

I felt guilty because he hadn't come.

'What about you?' I said finding his penis again and wanking it.

I wanked him for ages with no effect. I wanted him to come. I knew what I liked from women, so I went down on him. I pulled his foreskin back and licked his glans while my hand pumped away. His erection was gradually softening. Eventually, he said 'I'm not going to come'.

'You probably need a slash,' I suggested.

He was limp.

We got dressed and I made some tea before he sloped off home. I didn't see him again for nearly a year.

Next time we went for a drink, I invited Trevor back to have dinner with me. I didn't want to get quite so drunk this time. I had a vague ulterior motive too. While we were drinking, I remembered him rubbing my dick and rimming my arse and started to feel horny. I didn't have a new girlfriend yet.

I found a passage in a pornographic novel that described an older woman undressing two schoolboys and sucking one of them. I suggested that Trevor read the passage while I cooked.

As I was putting the dirty plates in the kitchen Trevor put his arms round me from behind. I could feel his erection against my bum. I leant back into the embrace.

'Do you feel like a cuddle?'

I thought his choice of words slightly dissonant, but turned and kissed his this time not so stubbly cheek and felt his groin.

We went upstairs and undressed. Suddenly, I wanted nothing but to suck his cock. I knelt and took it in my mouth.

'Get on the bed,' he said, almost commanded.

I thought he was going to fuck me. I wanted him to. I was glad he was so small; I could take that. I wanted to feel what having something up your arse, other than your own finger, felt like.

He arranged me on the bed sitting upright with him facing me, our legs interlocking. He was wanking me with firm, fast strokes. I tried to do the same to him but his erection was softening. When I came, it was so violent that my spunk shot up into his hair. It was one of those really excellent orgasms that happen when you least expect them.

We got up and had a drink – whisky I think. I soon started to feel horny again. I wanted him to use my arse but dared not suggest it. We were both, to all intents and purposes, totally straight men having a bit of fun. Anyway, that was my interpretation. It was summer and we had only put our shirts back on. I tried to re-arouse Trevor's prick with my hand. I went down on him again. The thrill of feeling something go from soft to hard in your mouth was new to me.

'Let's go back upstairs,' he said.

I wanked him on the bed for ages without a result. Eventually, I really needed another drink. I lit a cigarette as I poured them and was still smoking it when I returned to the bedroom and put the two glasses on the floor beside the bed.

'Why not suck me off while I finish this?' I said, indicating the fag by holding it up.

He knelt in front of me and sucked my engorged cock. I stubbed out the cigarette in the ashtray on the tallboy and took him back to bed, hoping I could make him come. Perhaps he would fuck me.

We wanked each other until I came on my chest. He obviously wasn't going to. I asked him about it. I felt guilty having all the pleasure.

'The truth is I just don't fancy men Colin. I really like being kissed and cuddled though.'

I never asked him to do it again on our sporadic outings.

*****

Months later, I started to fantasize about homosexual sex again. I eventually plucked up the courage to place an ad in the lonely hearts column. What should it say?

BI-CURIOUS, 38 but still too yellow to hang
round bars, wishes to meet similar for adventure.

I got three replies. The first one I binned; it went on about God. I'm a militant atheist. No that's the wrong word; I know there's no God rather than just believe there isn't one. Creative principle in the universe? Sure! But if there was an old geezer with a beard outside of the universe, we couldn't experience him. Time didn't exist "before" the big bang. The whole idea was self-contradictory and, if you thought about it, plain daft. I didn't need the distraction of listening to a God botherer during sex. I'd even dumped a gorgeous Chinese girlfriend because she had God.

I phoned the second man. He sounded like a career pooftah and talked about vicars and choirboys. When he told me he had lost and eye, it was the last straw. I was glad when he didn't call back.

The third letter was quite long and very erotic. The man described his fantasy of being slowly seduced by candlelight with soft music playing. He wanted to feel my spunk hitting the back of his throat. I phoned him.

'My name's Colin. You replied to my ad.'

'Hi. Thanks for ringing.'

'Is it OK to speak now?'

'Yeah, I'm alone.'

We told each other the bare minimum about our predicaments. I was straight up to now – I didn't mention Trevor – but wanted to find out if my fantasies were anything more than that.

'Your voice sounds sexy. I've got my dick out.'

I imagined it. I could feel my dick oozing liquid in my pants.

'Hey, you're getting me horny now.'

'Good. Let's meet.'

We described ourselves and arranged to meet in a bar in town the next weekend.

He had reddish curly hair and was slightly overweight though not grossly so. He worked for a television company. After our second pint of Adnam's, I decided I liked him enough and invited him home.

I tried my best to realize his fantasy. I put some Mozart on, opened wine and sat beside him on the sofa. My hand went to his knee and I leant against him. He kissed me and my hand felt his erection though his trousers. He felt mine. I unzipped his flies and put my hand inside them. His cock was already free of his pants. I rubbed it gently. He started to unbutton my shirt. I was getting impatiently horny.

'Shall we go upstairs and get it over with?'

He seemed disappointed at my alacrity, but we went upstairs.

I knelt and took him in my mouth. His dick was bigger than Trevor's but, to my relief, not huge. As I sucked him, I undressed. We fell onto the bed and wanked each other for a while.

'You've got a great cock,' he said.

'I've never had any complaints,' was all I could think of by way of reply.

I wanted to go down on him again and when I did, he found my prick with his mouth too. His foreskin was tight when my lips pushed it back over his glans. He started rubbing my shaft fast with his hand and I gave him his greatest wish. It was almost painful as he sucked and swallowed. Despite his best efforts, some of my spunk went on my chest. Somehow, I didn't like it when he smeared it into my body hair, but I wanted to finish him off with my hand. I still wasn't sure about the health risks of letting a stranger come in my mouth.

Despite trying, I just couldn't bring him off. What was I doing wrong?

We went downstairs for another drink and talked about music. When the bottle was finished, we went back to bed. I was feeling horny again and started wanking him. He did the same for me.

'Would you like to fuck me?' Maybe this would make him come.

'You'll have to wear a johnny,' I said.

I found one in a drawer and put it on him.

I lay back with my knees up and pulled my buttocks apart and he pushed into me. His dick didn't go in easily and it felt uncomfortable. I determined to relax but he wasn't pushing hard enough to get more than halfway. In the end, he gave up and we slept. He was gone in the morning and I never heard from him again.

I felt I still didn't really know what sex with a man was like. But I remembered imagining that I was a woman as I hugged him on top of me with his prick between my legs. Perhaps that was what I wanted.

I had tried on my wife's tights and shoes once – ages ago – but had never thought of going further. I suspect that lots of married men do that. It was an unusual feeling when your thighs rubbed together. I started to wonder how women feel in clothes that are normal for them. I would have to try.

I decided to buy some underwear and a dress from a mail order catalogue. I read the size guide and measured myself carefully. I chose a pretty lilac bra with matching briefs and suspender belt. I also ordered 3" court shoes, a short gathered polyester skirt and a gold blouse. I bought black stockings at the supermarket.

I felt just incredibly horny as I dressed up for the first time. Never mind the feeling of the sheer stockings; just doing up the blouses with the buttons on the wrong side was a turn on. The skirt swished around my hips and my legs looked shapely and sexy in the mirror. I had to have a wank immediately. When I looked again at my reflection, I looked ridiculous; my belly stuck out and my face looked like a man. I bought some make up and a book on how to use it. I ordered a basque and, oh why not, another pretty party dress. I couldn't wait for it to be delivered. I also ordered a long wig, which arrived two days later.

On Saturday, my nextdoor neighbour rang the doorbell. She handed me a parcel.

'I bet you'll look pretty in these,' she said.

'Sorry?'

'No, it's me who should apologise. I opened this before I realized that the courier had left it for you. My husband took it in.'

She knew I lived alone.

'It's a g...gift for my g...girlfriend,' I stammered.

'Of course. I was joking.'

I shut the door, relieved and rushed upstairs to make up my face and try my new purchases. This time the result was quite convincing. I needed to come.

About this time, I got a girlfriend by advertising in the classifieds. She was about my age. I usually went out with younger women. She was good company, quite good looking and had a very tight vagina for a women of her age. She had never had children. When she wasn't available, I still dressed up for the thrill of it.

One morning, Vera came downstairs in tears. She was holding one of my dresses. She threw it at me.

'You bastard!'

She thought I'd been seeing someone else.

I didn't want to hurt her, so I told her the clothes were mine and admitted to wanting to know more about how a woman feels.

'I thought the sizes were odd,' she said, as hers tears subsided.

'I'd like to see you in them. Would you dress up for me?'

She helped me perfect my make up and made tea while I dressed. When I came downstairs and twirled for her, she said 'You're gorgeous, Baby'.

She took me upstairs and I thought we would make love. At least she wasn't horrified by my perversion.

'You've been a naughty girl, deceiving me like that, pretending to be a boy all the time. Over my knee for your spanking!'

In my aroused state, I thought I'd like to try it.

She sat on my bed and I positioned myself across her knees for a spanking. She lifted my skirt and hit my bum. She spanked quite lightly at first but then harder until I was saying 'Ow!' every other smack.

'Let's get her pretty little knickers down and see her naughty bottom.'

The smacks hurt more with my knickers round my knees. I was begging her to stop.

'My naughty girl is naughty,' she said, putting her hand underneath me and rubbing my dick.

I couldn't stand it any longer. All I can remember is my long hair falling forward across her face as I shafted her. It was the best sex we'd ever had. She said so too, in a passionate and erotic letter she wrote to me the next day.

Somehow, I wasn't ready for this, and I stopped seeing Vera soon after. In the meantime, however, she took me to a couple of gay bars. She was a bit of a fag hag and had lots of gay male friends. I didn't like most of them. She wanted me to go dressed as a woman but I never had either the guts or the handbag.

Loneliness soon had me fantasizing about men again. I thought I would see what it felt like to cruise, unchaperoned, in a gay bar, and went to one of the ones Vera had taken me to. It was in Paddington.

I stood at the bar all evening as couples and younger, single cruisers ignored me. It was fairly quiet.

'Thursday, Luv! It's always a quiet night,' said the camp barman.

At ten o'clock, a smart, pinstripe-suited man came to the bar next to me and waited to be served.

'Can I get you one?' he enquired. His voice was like a Tory politician's.

'That's very kind of you. I'll have another of these. Thanks a lot.' I pointed to my bottle of Beck's.

'Think nothing of it. It's the least I can do before I take you home and fuck you.'

I was gobsmacked. Had I heard him correctly?

He ordered the drinks. I stared at him. Tall. Dark hair, greying at the temples. About my age. Looks after his body. Incredible eyes. They seemed to drill into me.

'Tell me about yourself ─ what is it?'

'Colin.'

I told him about my job and old girlfriends. He probed and soon got me to admit that I'd had an experience with a man. He wormed the stories of Trevor and the redheaded man out of me. He wouldn't let me buy him a drink. There was something intimidating about his smooth manner. I decided I'd better go.

'Thanks for the drinks. I've gotta go now.'

He glowered at me as I turned to leave. There were two bouncers on the door when I'd arrived. They were blocking my path now.

'Excuse me.'

They picked me up physically and brought me back to the bar.

'Take him out back,' said my erstwhile drinking partner.

I was shitting myself as the two thugs carried me through a door marked Fire Exit next to the bar. What were they going to do to me? Rape was my best guess. They pushed me out into a back alley. There was a white van. One of the men unlocked its back door while the other manhandled me inside. The other one shoved a rubber ball in my mouth, gagged me and hooded my head. There are no words for my utter terror as they chained my hands to the roof of the van and manacled my legs. I sat there blindfolded awaiting the outcome.

Soon, the van's engine started and I felt it move off. It seemed like a hour later when hands released my wrists from the roof and chained them behind me. I was led indoors, up a flight of stairs and through a door. The hood was whipped away.

I was in a plush bedroom. There were expensive looking prints on the walls. Amongst them, there were several erotic cartoons: pictures of women in severe bondage and men being sodomized.

My captor was the man from the bar. He was alone now ─ no sign of the thugs from the bar ─ but he looked fit and I was in chains. He kissed me deeply, taking my breath away. His hand went to my crotch and I could feel I was already hard.

He was undoing my trousers and pulling them down with my boxers.

'Kneel before you master, Boy,' he commanded.

I had no choice. I saw him undo his belt and trousers and get his tool out directly in front of my face. To my horror, it was gigantic, even bigger than my own. I knew what he was going to do me with it. It would hurt. I was about to plead with him to let me go when he shoved it into my mouth.

'Get it nice and wet, Boy,' he said.

I sucked and licked the massive thing, dreading his next move. His spunk filled my mouth in jets of warm fluid. Suddenly, I thought of my guilt with the other two men and was glad he had come. Instinctively, I swallowed and swallowed again.

'Good boy. Stay there.'

He left the room. I was too stunned to move. My dick throbbed with the need for release. He came back with a whisky bottle and two glasses.

'I'm going to take your chains off, Boy. Do you promise to be good for Master?' he asked, filling the glasses at an antique dressing table.

'Yes, Master.' The word just popped out of my mouth.

He produced a key and unchained my arms.

'Here, wash your Master's spunk down with this. It's a lovely accompaniment.'

He gave me a glass. The whisky tasted good, even mixed with semen. A single malt, I thought.

He unchained my legs and – I still don't know why I did this – I took my shoes and trousers off.

'Kneel on the bed boy and wait for your master to anoint you.'

I scrambled, terrified of him, onto the bed. He was pushing jelly into my bum with his finger and smearing it around the hole. I felt the bed give and his hardness push into me as he held my hips. It slipped in a little way. I felt as if I were being torn apart. It was agony. My sphincter pushed him out. He got off the bed. I heard a swishing sound and my arse exploded in pain. I fell forward as the belt descended on my bottom again and again. I was crying into the covers.

'Shall we start again?' The question was rhetorical.

He pulled me to my knees and pushed in again. This time, I relaxed completely and suddenly he thrust into me. It felt the size of a tree. He started to move in and out slowly and evenly. I began to get used to it but I felt totally filled and dominated. Was this how women felt. I was his girlfriend and he was in my cunt not my arse.

'Fuck me, Darling,' I heard my voice saying, coaxingly.

He reached under me and squeezed my cock so expertly that I came at once. I had never come so completely and satisfyingly. I didn't want him to pull out when he did. My cunt felt empty as Master's juice ran out of it.

He cuddled me tenderly for a while.

'I'm going to tie you up, Boy.'

He produced a leather harness and slipped one of its metal rings over my now-limp penis. He buckled it on as I lay there helpless to challenge his will. He cuffed my hands and legs and fastened the cuffs together by chains so that my legs were pulled up my back by my arms. Then he covered me, undressed and joined me in bed.

In the morning, he unbound me except for the body harness. He told me how to find the toilet and I went and came back to his bed. Master rubbed my cock. It hurt as the penis ring bit into me but my erection kept growing. It throbbed. I felt empty.

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Disclaimer: All posted stories include descriptions of sex scenes that could cause offence to some people. Please do not read this story if you are offended by perverse sexual material, or if you are under the legal age of consent for your own country. These stories are pure fiction and are not based on anyone living or deceased.