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Holiday to Remember

Category: Anal Sex
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There we were, Alex, Joe and myself, 3 co-workers on a weekend break to Brighton, England. We were to be staying at Joe’s friends farmhouse for two nights to get away from the city life and enjoy a few days fishing and golfing.

I was driving, heading along the highway when Alex asked “is it a big house, where are we going to sleep?”

Joe explained we were all to be sleeping in the farmhouse but we were both taken back when Joe revealed there were only one single bed and one double bed. It quickly dawned on the two of us that one of us would have to share a bed with Joe, both Alex and I knew what a well hung chap Joe was!

Joe was now in his late thirties and had quite a reputation amongst the ladies at work.

I asked “who gets the single bed?”

“We’ll have to toss for it,” suggested Joe.

“Whoever gets the same side will share the bed!”

We stopped the car and all tossed a coin, Alex called out first,


I looked down, I had tails, I was relieved I wouldn’t be sharing a bed with Alex, then I realized whatever side Joe threw he would be sharing with one of us tonight.

“Tails!” Alex shouted out.

“Which lucky one of you will be sampling my python tonight then,”

“it’s not me,” Joe was grinning with delight, a shiver crept down my spine as I sank into my seat and dreaded the rest of the holiday.

There were a few jokes during the rest of the journey but what was there to worry about, Joe was straight as was I and we were both married, what harm could come I kept telling myself?

That evening we all spent the night in the local pub, we all got drunk on beer and whisky and then about midnight we returned to the farmhouse. We were all a little tired and after a coffee went up to our rooms; sure enough there was a double bed in one room for myself and Joe to share. I quickly cleaned my teeth, stripped down to my boxer shorts and got into bed.

I didn’t want Joe to see me changing as my penis was just about 6 inches long compared to Joe’s legendary python, but I couldn’t help discretely watching as Joe undressed and then got into my bed. There seemed to be quite a bulge in his pants, I wondered if he was semi-hard or could he really be that big while flaccid. All seemed to be fine as we said goodnight to each other and joked about how the local girls had rejected Alex’s advances. Soon enough the light was turned off and I faced away from Joe and went into a doze. I couldn’t get out of my mind that such a huge cock was just a couple of feet away, my cock began to stiffen at the thought of what may happen and I wondered if his cock was also stiff. What was he thinking about, was all the joking about taking my virginity just a tease?

The nearest thing that I had got to anything close to thinking any gay thoughts was when I experimented by cross dressing in the bedroom several years back, when I tried my wife’s knickers and suspenders on in private. Tonight seemed a little different, there was definitely some nervous tension not knowing what was to happen.

I lay there for ages, then he started to stir, suddenly I felt a hand come over my waist.

“Sheila, Sheila,” Joe whispered.

He seemed to be dreaming and then he rolled back to his side. Phew, what was that about, Sheila must be his wife? Surely he won’t confuse me for her?

Then I sensed him lying behind me, first the warmth of his breath on my back then there was that bulge pressing along the back of my boxer shorts, sure enough I knew what it was but it was growing, it felt twice as long as mine. Again an arm came over my waist and a hand pressed on my tummy, then it traced its way down and lightly gripped around my now stiffening cock and started to gently massage it, I had to admit it was enjoyable but it felt wrong. What should I do now? This was the time to stop it or just take whatever was coming. I just laid there and enjoyed a few minutes of gentle strokes, then I felt a tug on my boxer shorts and they were gradually lowered below my ass cheeks.

Nothing was said at all. Next I felt a finger trace up and down between my ass cheeks and then suddenly a cold feeling as an oily finger was lubricating around my ass. I winced as a finger entered my tight ass, my sphincter stretched to accept this foreign object which gently stroked in and out of my tightness. It felt strange but exciting; would I really let him force his huge cock in my ass, could a virgin ass take the biggest meat in the factory? Would he tell everyone at work what an easy fuck I was? What would my wife say if she found out? Would he split me in two?

Then suddenly he let go of my cock and turned me around facing me down with my ass slightly raised in the air and he put his hands on my waist. I felt a soft warm object firmly pushing at the entrance to my virgin ass.

“Just relax,” Joe said.

I tried, my heart was beating like never before, I tried to relax and pushed back gently to feel my sphincter starting to dilate, it was stretching and stretching, could I take such a cock? How big was it? I hadn’t really seen it but it felt huge. By now the head was just in, it was painful, there was no going back now, he rested it with the head inside of my anal ring for a minute letting me get used to the stretching and as we both felt my ring relax around his penis he then moved forward pushing in two more inches inside me. He rested then pushed another two inches inside of me, then another two. I reached behind me, I touched his cock at the entrance to my ass, to my shock there was still 4 fingers width to go in. I already felt more than full as he pushed forward again.

He started slowly thrusting his cock inside me, the rhythm was slow, I tried not to make a noise so that Alex didn’t know about our secret and bit the pillow hard, he was now going for it and I felt his wiry pubes on my ass cheeks, I now knew he was completely inside me and felt some achievement at taking this 10 inch monster inside of me. For ten minutes he pounded my ass and as he did so I felt his hand reach around and grip my penis. After four or five strokes I felt my body stiffen and he increased the stroke rate until he had me on the edge of my first orgasm. He stopped the thrusting and pushed in as deep as possible. My ass tightened around his cock, my body trembled as he milked my cum onto the sheet below, the biggest orgasm I have ever known, I moaned out aloud and then slouched forward onto the bed but I was still impaled on his rigid pole.

I could feel my warm sticky cum on my belly from the wet sheets below and he stated to fuck even faster than before. I started to feel a throbbing feeling from within and then he erupted, spurt after spurt into my invaded ass. After he had finished cumming he lent forward, and we rested both having been fully pleasured. I felt his cock gradually shrink and slip out of my stretched ass. Cum trickled down from my ass and down my crack. I felt so guilty but ecstatic.

We lay there and a few minutes later he turned me over and knelt in front of me

“now clean me up.”

Automatically and without protest I licked at his semi-stiff cock. I thought it would be revolting but the taste of myself and his cum was getting me hard again and my licking was getting him hard too. He had complete power over me. He then pushed his member against my lips and I opened my mouth to let it in half way, this was all I could take as it pushed against the back of my throat. I tasted his pre-cum and he upped the stroke rate, ten minutes later I felt his penis throb, there were three long strokes and my mouth was filling up with warm sticky cum. It dribbled down my chin and onto my chest and stomach, I licked his cock a few times as it left my mouth and we laid down in the spoons position with him stroking my cock to a second cumming. Later on we fell asleep and we carried on the next day’s touring as if nothing had happened.

Alex asked me at dinner if I wanted to swop rooms and I instinctively said,

“no way, that’s fine you won the toss!”

After we returned to the house on the second evening we were joined by Katy, the 22 year old farmer’s daughter. There were lots of whispering between Joe and Katy and I’m sure she knew what had gone on the night before. She was pretty, very slim and had long blonde hair with big tits and I wondered if she had tights or stockinged legs under her denim skirt. All night Katy gave me cheeky grins and was very touch feely. I quite enjoyed the attention and wondered what was in store for later. I had noticed while playing pool that she had indeed leant forward revealing her hold ups, this did nothing but increase my sexual tension. Things went similar to the night before and we retired to bed with Alex and Katy going to their own rooms. I went to bed and laid there waiting for Joe’s hand to come over my waist again but nothing developed and I disappointingly went to sleep.

I awoke in darkness to feel a gentle hand playing with my genitals, and then warm lips sucked on my now stiff cock. I laid there enjoying it pretending to be asleep, there was a women’s touch and a scent of perfume and it must be Katy I thought. She then rolled me over and pulled me into her, my cock burying itself in her wet snatch, my legs sensing her stockinged thighs got my heart beat racing and made my cock even harder.

This was great but then I felt two hands on my waist, they were larger hands; I knew it was Joe but I kept on pumping into Katy regardless. As I pulled back before thrusting again I felt his cock against my now sore ass, he pulled me onto his pole and again I was impaled. I continued to thrust into Katy, every time I did this his cock pulled back then thrust forward as I came back to meet him, then he started to push me into her with long deep strokes. I had my cock in her wet and warm vagina and his cock stretching my ass again; now Joe was controlling us both with his thrusts.

The soreness was overtaken by a magnificent orgasm and I cum into Katie’s virgina as she came too, gripping me into her as tight as she could, reaching for that extra length which I lacked. Again Joe thrusted quicker and quicker in and out of me and he took no more than a minute more or two and he came in my ass for the second time. His cum inside of me was easing the soreness as he stroked slowly to a finish. Joe leant forward, he had finished, we were all connected together and all completely sated, Katy then joined me in cleaning up Joes cock with our tongues and then she disappeared to her room.

Joe had me wear a pair of Katy’s knickers we had found in the bed sheets, he had me twice more during the night, the first time in doggy position and the second time with me on top collapsing on his chest as I came over his belly, all of which he made me lap up until he was clean. We went to sleep with his cock pressed up against my silky knickers.

Back at work Joe said nothing about the weekend. I can’t wait for another trip to be arranged and I regularly wear my knickers as a reminder of the events of that Brighton weekend.

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