True Story

Get Drunk with me

It has been long since I wrote something but to make up for the lost days to my funs I think is about time I give you a true story about my friend and I. I changed her name in the story, just in case

First Anal, with a Man Pt 2

If you haven’t read My First Anal with a Man, you might want to, to get an idea of the first time I got fucked, and to give you some background for this story. It’s not required, but it might make it easier for you to follow.

A Short Train Ride

A Short Train Ride
I bumped into him at the porn club where I usually took a bottle of wine to share with the manager Brian. I had been a member so long that I only went downstairs to the two small cinemas when a couple came in to play.
That evening whilst chatting with Brian, a friend of his came whom I had seen before but not really got to know. We shared the wine and got on to our main interests that drew us to the club- wonderful horny women who liked to play. He and I got on really well.
He then made a proposition to me that was quite a challenge. I agreed and would wait for him to phone me on my mobile when it might happen. This is the story of what actually happened.
I had forgotten about the chat at the club. Then out of the blue Stan rang me and asked me if I was still interested. I replied, “Of course.”
“Well Sheila and I are coming up to London tomorrow for the day for a bit of what she loves and I wondered if you would like to partake in a little fun. She doesn’t know I rang you but she knows I can arrange this kind of thing.”
We agreed to meet at the hotel at Victoria Station, one of the main lines into London, at 1030 in a bar we both knew. I wasn’t to greet them but when we had both arrived I would go to the loo where he and I would make arrangements.
I arrived just before 1030 and ordered a coffee. About 1040 they arrived and Stan gave me a wink and settled down with Sheila nearby. So I had a good view of her as she sat sideways to me about 12 feet away. She was blonde about 45-50 and quite trim and wore heels and stockings (I thought) and a light black cotton coat buttoned up, but without a belt. Her breasts were not too apparent under the coat. I had to imagine what she wore under the coat.
Once they settled I rose and went to the loo. I was followed by Stan. He said she’s game. In fact they had a bit of fun on the way up from Brighton but that’s another cameo. We agreed I would go out of the hotel first and wait for them to come out and follow them.
Once back in the main station, after a few minutes they emerged from the hotel and began to walk to the underground. I immediately followed them down the escalators to the underground to join a train going north. I kept a few feet from them but never got too separated. The platform was very crowded and I began to lose sight of them. Don’t panic Ian I thought. But I then heard the sound of the train in the tunnel at some distance but they approach fast. I moved along as quickly as I could, then suddenly I saw her blond hair. They had walked some way along the platform and waited. The train arrived quite crowded. I moved closer to them and got on behind her and Stan was in front of Sheila. We were at the end of the carriage where there is a single door. I was the last in. The doors closed and we were wedged. Sheila had her back to me and Stan provided cover for both of us.
The train picked up speed and she relaxed a bit. Because the train was crowded her back was pressed against me. I found myself in a position I had imagined but didn’t possibly think would actually happen.
Tentatively, I moved my hand to her hips and over her rear and just pressed a little toward her. She pressed back firmly on to my growing hardon. I took that as a yes. I moved my right hand down her leg at the back and tucked into her coat. I began to slowly lift her coat running my hand up her leg and thigh over her stocking. Yes they were stockings. I had reached her soft flesh. Her continued pressing against me encouraging me to go further.
Her flesh was deliciously warm as I stroked that warm softness across her upper thigh at the point where it met the cheeks of her bum. No apparent panties. She seemed to like what I was doing as she pressed more firmly against my groin. Encouraged and running my hand round her thigh I ran into plenty of hair and noticing she was indeed panty less. My fingers explored her hairy wet warm cunt as I slid across her soaking labia and into her vagina and up across to her clit. With my other hand I suddenly found that her sleeve was a wide one enabling me to move inside the sleeve under her arm pit on to her chest and across to her left breast. The nipple was tight and stiff from a slightly floppy but fullish tit.
She squeezed even harder against me in silent recognition of my sexual onslaught.
The train began its deceleration into the next station. I thought it was an all too brief sexual interlude. I was right up against the door. Fortunately the platform was on the other side of the carriage. I paused. Sheila didn’t move or look back at me as if I was still a stranger in the carriage whom she had to involuntarily squeeze against. Stan winked at me in recognition of my, so far, successful exploration of his partner.
More people got on the train than got off. So the effect was more intimacy. But Stan controlled the pressure on us. He didn’t want to make it impossible for us.
Slowly the train began to speed up leaving the station. As it did so I resumed my movements on her clit and tightened my fingers on her hardened nipple. At full speed Sheila was getting into a beautiful rhythm as my finger slipped and slid around and across her stiffened clit. Pressing her nipple really hard, she began to tense her whole body. Glancing at her face, she had clenched her eyes, her lips silently braced and she came in my hand as I increased the pace on her little power source. I heard her quietly squirm at the pinnacle of her cum.
As she came down, she took her hand out of her pocket where it had resided, her other hand on a vertical rail for support, and squeezed my erection in recognition of her induced orgasm. Stan just gleamed at both of us. He looked pretty high too. All this in the space of what felt like five minutes.
I was on a high too but thought, well at least I’ve provided a good service even though there was not much more she could do for me.
The train slowed again. She signalled to Stan that she wanted to move on, gave me a final warming grip of my cock and moved out of the carriage.
I quickly made the decision to follow them. They were changing train lines, involving a change of platforms. I was becoming expert in keeping up. Though it was about 11 in the morning the underground was still busy, with visitors and tourists who just got in my way as they struggled to make sense of where they were going. My knowledge of London’s underground enabled me to follow them on their way to another line and platform. Going up an escalator, Stan viewed me from the neighbouring escalator and winked again. Sheila didn’t see me.
Arriving at the next platform, I followed a few yards behind and waited, as did they, till the next train arrived. This time I was able to get in with them. We found ourselves, again at the end of carriage except that Sheila was standing and resting against a bum rest facing out and I was directly in front of her with the door to our right and Stan to my left. Again, beautifully tucked in.
“Weren’t you on the last train? Sheila beamed at me as I responded, “Yes, my pleasure.”
I moved forward feeling encouraged by my covering of her by my full winter coat, by her comment and slipped inside her coat to feel her stockinged thighs again. She helped me by undoing one button on her coat, enabling me to slide my hand up beyond her stockings to her still wet pussy.
However, this time she went for my zip inside my open coat that provided a cover for our activities. I had decided when I prepared for this morning not to wear underpants. So when she began to explore she found herself stroking my cock already hard. We played with each other.
“Here darling let me look after you this time.”
There wasn’t either the time or the space to be able to fuck without being observed but Sheila took both hands to stroke my balls and wank my cock as I also fingered her wet pussy that had leaked onto her thighs. I slid a spare hand in her coat to grasp her nipple again and gave it a squeeze. She smiled and quietly whispered in my ear,
“Darling, you’re not good at taking instructions are you? Let me look after you. Just hold me. Don’t try to get me off again – no time.”
For some reason my eyes scanned to the right of Stan. Looking very closely at me was a woman in her late 50’s giving a very searing look at me and Sheila. In an instant she knew exactly what was going on. I was just about to panic and attempt a quick withdrawal when she just smiled benignly at me, giving us a silent acquiescence. Fucking wonderful. The world can be just brilliant. Sheila was not in a position to see or be aware of this potential, but averted, blow to our pleasure.
I smiled back and relaxed just holding Sheila’s warm soft thighs.
“Cum for me now. You look ready. Just shoot at my pussy. Don’t worry about the mess I love it. I had a lovely mouthful on my way up on the train. Yours will add to my creaming.”
In my ear she murmured, “Yes let me have it now.”
Just as she made the comment I felt her hand harden on the head of my cock, much firmer than she had been doing. I had not cum for a day or so. As I went over the top, not making my usual noisy outburst but stifling it in her hair, she kept going, rubbing every drop of spunk out of me as it shot out and slid on and down her pussy hairs.
She let go and I slipped back behind my open zip. I gave her a warm hug just as the announcement came for the next station. We smiled at each other. I glanced at Stan who returned my smile as did my observer who realised what had happened and just beamed at me. Sheila gave me a final hug just as the train slowed at the platform. I kissed her cheek and wished her a lovely time for the rest of their travels.
I got off the train with the sexual observer right behind me. I caught her eye again.
“Some people get all the luck don’t they? Thanks for the show. Wish it were me.”
I was just going to reply when she was joined, by what appeared to be her partner or friend and bid her, “I wish it were to.” We went our separate ways.
It was really just a quickie, but a very memorable one that depended on impeccable timing and good luck. I was aching to share the story with my closest friends but only the ones I could trust and who knew me well. Brian, back at the club loved the retelling. I’ve enjoyed sharing it, once again, with you.
And the cameo on the Brighton line? They found themselves in an empty carriage with just a young 18 year old opposite and facing them. For Sheila it was just too, too tempting. She slowly opened her stockinged legs to the young man. At first he didn’t notice but he looked up a little from his mobile on which he had been texting and found himself looking at her knees. She continued opening her legs until her tops were revealed, then, and in the full light of the morning sun, she displayed her pussy hairs. Seeing his response in his groin she used her fingers to open wider and revealed the glory of her glistening wet lips. His eyes rove between her pussy and her face to see her intentions were aligned with what was happening. He registered positive as his cock began to harden.
Nodding to Stan to keep an ear and eye to passing passengers, she reached forward to his zipper and pulled it down and dug for his cock. Pulling it out she leaned further forward and took his hardon straight into her mouth. She proceeded to suck him to an extremely quick climax, deftly swallowed his load, wrapped back behind his zipper, stood up, blew him a kiss and departed to another carriage with Stan. (This little cameo was relayed to me by Stan back at the porn club a week or so later, when we reminisced about our underground travels with Brian).

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Forced To Be Female Part 3

During those days other inmates constantly made fun of me, spit on me, groped me and told me that soon everyone will be getting some of that pussy. I was asked if I liked it, has Mike split you in two. Don’t you want some white cock or is dark meat all you enjoy? It was constant and the only time I could get away from it is when I was alone. I was always scared, scared of what Mike may do, scared that someone will find me alone and rape me and scared that this would never end.
After those 3 days Mike decided I was healed enough to fuck. He came down to my bed after lights were out and had me dance for him. When my ass was facing him he started to pull my panties down. He lubed himself and finger lubed my ass. It hurt with just his finger, I hated to think he was going to stick his cock back in me. He spoke to me gently and told me we were going to take it real easy. He said that he wanted me to enjoy it. I thought to myself that I could never enjoy this, but I didn’t tell him. He lowered me on to his cock slowly, he told me to make soft moans, so I did. As it pushed against my asshole, I reactively tightened and he told me to be easy, if I am tight it will hurt. Try to loosen up for me. I tried and it worked somewhat, it went in slowly and didn’t hurt as much.
He held my hips and made me get into a rhythm. He kissed the back of my neck and rubbed my bare legs. I could tell he was getting ready to get off, because he picked the rhythm up. Finally he stiffened and shot his load inside me. It felt like he had gotten off a lot, because it felt hot when he got off. I was so grateful it was going to be over. When he finally pulled me off him, I was facing away from him and he punched me in the kidney. I doubled over in pain. He started to ask me something about the mustard bottle. He asked me if I had used it. I had actually forgot about the mustard bottle (for douching) and I said no. He grabbed me by my hair and put something sharp against my throat. I couldn’t see what it was but I was scared. He told me to get on my knees and I did it immediately. I could tell he was really mad. He said look at my dick, I looked at it and it was flaccid by now, but if had shit on the head and mixed with cum and grease. It was gross. I told him I was sorry and that I would use the mustard bottle from now on. He still had a hold of my hair and he told me to clean it. I started to look around for something to clean it with, and he pushed my head closer to his dick. I said Mike, I can’t do that. Please don’t make me do that. He said clean it, and pushed me closer. Mike, please no Mike, I said. He told me to open my mouth and put the sharp object next to my ear. I opened my mouth and put his whole dick in. I closed my mouth with my lips and drew back to bring the mess into my mouth. When I pulled off his dick he grabbed a wash cloth and made me clean what was left off. I still had this mess in my mouth and wanted dearly to spit it in the toilet. He held my head with one hand and put the sharp object next to my eye. He said that there was cum in my mouth with that shit and we don’t waste cum. Swallow it. I couldn’t say anything, I shook my head and he said again swallow it. You don’t need this eye to be my bitch, so swallow it or lose the eye. I swallowed it and started gagging he then let me go so I would not gag on him. I puked in the toilet and when I went to the sink to wash my mouth he grabbed my hair and threw me on the bed. He said I think I want you to learn a lesson from this, so lay there with that taste in your mouth until I decide you can wash. If you puke, you will clean that up to, so I wouldn’t puke. I laid there trying not to taste the inside of my mouth. I could feel it in my teeth, stuck in my throat, and all over my tongue. I didn’t move anything in my mouth. Saliva started to form in my mouth and I had nothing I could do with it except to swallow it. Finally after what seemed a lifetime, he let me wash my mouth. This took a very long time. I couldn’t get rid of the taste.
The next morning while I was making Mike’s bed, he told me that I need a new name. My new name will be Society. If anyone other than a guard calls me by anything but Society, I need to ignore them. Everyone needs to learn your new name. He also told me to see one of the queens and ask how to use the bottle, if what happened last night ever happens again, I would be eating shit for a week. Another thing he said, training starts tonight. I asked him what he meant and he said he didn’t want to ruin my surprise.
After supper I rushed back to our cell and used the mustard bottle to douche with. I needed to make sure I was clean. I didn’t want to go through a repeat of the night before. I finished just before Mike came back for evening count. After count Mikes 3 closest friends came to our room and I served coffee and a pack of cookies. He made me dance for everyone. They were grabbing me, pinching my nipples and pulling my hair. Two of the guys left the room and stood outside the door talking. Mike told me it was time to train. The other guy pulled my briefs down and pulled his cock out. Mike pulled his cock out and told me to get on all fours. He got on his knees and grabbed my hair and pushed my mouth on his cock. The other guy was lubing my ass with his finger, I felt his cock push slightly against my asshole, just before he slammed it into me. I wanted to scream but Mike just pushed his cock deeper in my mouth. The guy was fucking me hard and tears was coming down my face mixed with makeup when I was abruptly pulled off Mikes cock and the guy pulled out of me to shove his now ejaculating cock in my mouth. Mike took the other guys spot in my ass. My asshole was burning and the pain was shooting into my stomach when the first guy finished buckled his pants and left the cell. Another guy came in and pushed his cock in my mouth. Again I was pulled off the guy I was giving head only to have Mike push his cock in my mouth. He blew his load all over the back of my throat and on my tongue, when I felt the next guy enter me from behind. Mike didn’t leave the room he watched as the next two fuck me and shot cum in my mouth. When they were done, I went to the shower room. Twelve shower heads in a single room. I was showering and crying when this big black guy came over to me and told me that he had heard that I had some training tonight. He said that I would need that training for when it came time to take his cock and he grabbed my hair and made me look at his cock. It was huge, it was huge while it was soft. He let me go and I finished quickly and went back to the cell.
It wasn’t bad enough to have used me like they did, but they made a point to make fun of me. They asked me how they tasted, who came the most, which dick hurt the most and if I could taste my ass on their cocks. Mike told me that it was a good thing I used the mustard bottle. I would have been licking up quite a mess if I didn’t. I went to my bunk and didn’t say anything. Finally after they left and lights went out, Mike sat on my bed and asked me if I felt sexy. He said that all of his homeboys want to fuck me and they think I am sexy. I lied and said that I did feel sexy knowing everyone wanted to fuck me. He made me give him a massage and when I was done he started stroking his cock. He told me to bend over so he could see my ass, pose for me he said. I did and swayed my hips for him. Surprisingly he got off quickly, but when he did he made me lick the cum off his hands and fingers. He said remember cum is yours, none ever goes to waste. I knew you would be a good bitch he said. I think I will keep you.
The training went on for two weeks or about that. Every night 3 or 4 guys fucked me, rarely the same ones. They started playing games and instead of cumming in my mouth they would shoot it on the floor or on the toilet seat or on their own feet and make me lick it up while they laughed. It was explained to me that they couldn’t get off inside if someone else was going to use my pussy. It wouldn’t be right.
After the training was over, I was told that it was time to make some money. Society is going to make some money he said. I was to go to my room after count and get ready (put on panties, makeup, shave, and douche.) One of Mike’s homeboys would be outside my door to take money and watch for the guard. I was to have a pair of sweatpants handy incase a guard was coming, but most of the guards could care less what was happening as long as they didn’t have to do anything. I would service the customers $3 for head and $5 for a fuck from 6 to 10 weekdays and 6 to midnight on weekends. My first customer was the guy from the shower. When I saw him come in the door, I was immediately scared. He came over to me and his first question was if I had sucked any cock that day. I told him that I hadn’t and he grabbed me and kissed me hard, putting his tongue in my mouth. I was shocked, but I responded and kissed him back. He stepped back and told me to pull his cock out of his boxers. I moved closer and reached my hand into his boxers and held his cock. I pulled it out, it was partially hard and huge already. I told him that I wasn’t sure that he won’t hurt me with that. He said we would go slowly. He made me lube him up, but not with the hair grease that we usually used. He had a bottle of baby lotion. I squirted the lotion on his cock and rubbed it all over, making sure to use a lot. He had me bend over the bottom bunk and squirted some up my ass. He was true to his word. Slowly he pushed in, pulled out when I couldn’t take it and tried again. After 6 tries he was able to get it in. I thought I was going to die. He started slowly and didn’t bury it. He went easy, talking to me, telling me that he knew he was big and how he gets turned on by seeing how much pain his dick causes. He started to pick up the tempo, going deeper and it really started to hurt. I told him it hurt and he asked me how much. I said it was really bad and he started to really fuck me hard. He said that he uses baby oil instead of grease because it tends to dry up and he really likes to see his bitch squirm. I started to scream, telling him that I couldn’t take in anymore. He laughed and kept on until finally he pulled out and squirted all over the floor. I went down on my bunk in pain, I was sobbing at this point. He grabbed me by the hair and pushed my head on his cock. I was choking, I couldn’t breathe and he finally let me go. He pushed me on the floor and told me to clean it up. He put his foot on my back while I did. When I was done, he pulled me up to look at him and told me that he would be a regular customer. I like that pussy and your squirming. I will be back tomorrow.
I had two other customers that night. One fucked me and I could barely stand it. When Mike arrived I told him what had happened and I didn’t think I could do it again without it ripping something inside me. He told me he would make a rule to use grease. The next night I was surprised when Mike told me I had the night off. He told me that he didn’t want me to have to go to the infirmary. I was relieved. He made me stay in the room to rest my pussy. I was there about an hour or so under my covers so anyone coming by couldn’t look at me through the window in the door. I started to feel a stirring in my groin. I had not masturbated since I got to this prison. I closed my eyes and thought about my ex-girl friend. I couldn’t seem to keep her firmly in my mind, she kept getting replaced by black cocks in my mouth and in my ass. I stopped masturbating and started telling myself that the stress of all this is the problem. I went to sleep.

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