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I never realized the pleasure that could be derived from anal stimulation until an old girlfriend slipped a finger up my ass while working on my cock one time.

She had my cock pretty well lubed up, with the excess finding its way down the crack of my ass as she worked my shaft with one hand and my balls with the other. She eventually moved from massaging my balls to running her finger down the crack of my ass spreading the oil and teasing my tight puckered hole with each pass.

I was surprised at how aroused this was getting me. She sensed this and continued to tease me as I pulled my knees up toward my chest to give her better access. She worked the tip of her middle finger just inside of me. I could feel my sphincter gripping her fingertip until she quickly withdrew, causing my cock to flinch.

She applied quite a bit more of the lube and was back to teasing me again. By this time, I had taken over stroking my own cock. Her finger was circling my tight hole, teasing me, probing me. I suddenly felt her penetrate me again. A surge went through my body as she pushed it all the way in. My cock was engorged and felt thicker in my hand than ever before. She pulled out slightly and plunged into me again.

After adding even more lube, she added a second finger and went to work on my ass. Slow and steady at first, but it wasn’t long before my cock tensed up and started blowing a big load all over my stomach and chest. That was the absolute most mind-blowing orgasm I ever had up to that point in my life.

Fast-forward ten years. The girlfriend was ancient history, but I continued to fantasize about it, and always enjoyed anal stimulation. I would occasionally use my finger or a small probe when I masturbated, but nothing close to a real cock.

I wasn’t attracted to men romantically, but I really started to wonder what it would be like to have a real cock inside of me. It became a fantasy of mine, but I never had the opportunity to make it happen in real life. I couldn’t risk meeting someone locally as I lived in a very small town.

I traveled for business a couple of times a year. I had plans to attend a trade show in Chicago, and decided this would be my chance to make my fantasy come true without worrying about being recognized. I signed up on an adult “dating” site, and did a search for guys looking for guys in that area.

I ran across a post from a guy around my age in the M4M section. He was going to be in town for the week and was looking for a good time. I responded to the ad with my stats, a neck-down nude photo, and that I was a first-time bottom. I added that I would be in Chicago while he was there, and included that my hotel was just down the street from his.

I got a response a couple of hours later. He said his name was Mark, and suggested we meet somewhere for a drink after I got settled in. After a few back-and-forth emails, we exchanged numbers and agreed to meet at the bar at my hotel.

I spent most of the next day dealing with airports and planes, but made it to my hotel a couple of hours before my meeting with Mark. I checked in and unpacked my suitcase. I wasn’t prepared for what I hoped would happen later, so I headed down to the drug store on the next block. I bought some condoms and the lube I like.

I showered and put on jeans and a polo shirt. I got to the bar five minutes early. Mark said he’d be wearing a black jacket, and I spotted him right away. He was sitting in a corner booth. He saw me and waved. I headed over to join him. Mark rose to shake my hand. We sat down, and he gestured for the waitress.

We made small talk getting to know each other, and the mood got more relaxed after a few drinks. We eventually got back on topic. Mark asked me what I thought about taking our conversation somewhere more private. I paused for a few seconds, realizing this thing was about to get real. I said we should. Since we were in my hotel, I invited him up to my room.

We quickly finished our drinks, and I signed the bar tab. Mark followed me to the elevators. I felt nervous with anticipation as we rode the elevator in silence to the ninth floor. Mark followed me to my room.

Once inside, I grabbed two beers from the minibar and Mark took his jacket off, making himself comfortable on the small couch. We started making small talk again, until Mark asked me what I wanted to do. I told him that everything I wrote in my email was still on the table. I admitted I was nervous, and asked for him to take the lead. He said I could stop him at any time if there was something I wasn’t comfortable with.

I moved over to sit on the bed and watched Mark get up and start undressing. He was my age, but I could see he was in a little better shape as he shed his clothes. His cock was noticeably bigger than mine. I stood and undressed myself.

I stood there naked, and Mark guided me to my knees. I reached out and touched Mark’s cock, which was already about half hard. I wrapped my hand around it. I felt him grow in my hand as I started stroking. Mark whispered for me to suck it. I licked my lips and took him into my mouth. I started working my mouth as far as I could down his cock. He let out a sigh, and suggested we move onto the bed.

Mark got on his back, and I resumed sucking his cock. I stroked him while my lips and tongue concentrated on his head. I could feel and taste his pre-cum on my tongue. The taste and smell had me mesmerized. After a few minutes, Mark stopped me. He grabbed the pillows and put them in the middle of the bed. He instructed me to lay over them on my stomach with my ass in the air.

I felt Mark’s manly hands massaging my ass and running his fingers in between my cheeks. I told him about the lube in the plastic pharmacy bag on the table. Mark retrieved the bag and pulled out the lube and the condoms. I stayed in place and soon felt the cold glob of lube on my ass.

Mark worked the lube where it needed to go. He teased my hole and gradually made entry. His finger was much thicker than I expected. He worked it in and out slowly, adding lube and venturing deeper with each push. His finger was going in and out at a nice pace. I felt myself relaxing and taking it inside me easier. Soon, there was more lube and a second finger. After a little discomfort at first, I was really starting to enjoy it.

Mark carefully pulled his fingers out of me and rolled me onto my back. He had me hold my legs up, opening myself to him. I watched him stroke his cock and put a condom on. My heart was racing. Mark briefly stroked my cock until I was hard again, lubricating it along the way. He stopped and told me to stroke myself. I complied.

I heard the tube of lube slurping so I knew he was covering his cock with it. I soon felt the pressure of his cock on my opening. Even after loosening me up before, I knew it would be more than his two fingers going inside of me.

He teased my little puckered hole, rubbing his cock up and down. He started putting pressure on my tight ass and I felt him push in, slowly stretching me until my sphincter opened up and he slipped further inside. I gasped and he pulled back. I could feel his heat inside of me. After a few slow and measured strokes, I was almost fully open to him. I felt him slowly pick up speed and depth. I continued stroking my cock as he pushed all the way inside me. I thought I would cum right then.

Once we got a rhythm going, Mark was fucking me fully. My body was offering no resistance to him. I thought it would hurt more. It did at first, but it felt so good now. Mark changed angles and started taking shorter quicker strokes. He repeatedly hit my prostate gland. I started having what felt like a full-body orgasm. It was a totally natural body high. I can’t think of any way else to describe it.

I had stopped stroking my cock and held my own legs up so Mark could really fuck me. I started feeling the rush making its way throughout my whole body, culminating in a hands-free orgasm that sent cum all over me. Mark went for another minute and tensed up, pushing in to the hilt. I felt his cock swell up as he pumped cum into me. At that moment I wished he were bareback so I could feel his cum filling me up.

Mark slowly pulled out of me, and collapsed next to me in the bed. I leaned over and rolled the condom off. I sucked his cock clean, savoring the taste. He seemed surprised I did that. Mark dressed and we said our goodbyes. We agreed to meet for dinner the next night at his hotel.

After Mark left, I sat alone in a hot bath collecting my thoughts. I couldn’t believe I had just let another man fuck me in the ass, and even more surprised at how much I enjoyed it. I wished it had lasted longer, and I definitely wanted more. Perhaps Mark would take his time the next night, if I could be so lucky.

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Growing up in a family of four, it was just my sister and I. I was the older brother by a year and a half. We were typical siblings. We could get along great one moment and be at each other’s throats the next. We experienced a pretty normal childhood. My mother and father are both tall. My father is 6’4” and my mother is 5’9”. So it was a matter of time before my sister and I grew to be tall as well. I was a late bloomer not getting most of myheight until high...

Incest

What happens in Vegas0

"Fuck those Bitches" Cindy thought as she stumbled back into the casino. This was suppose to be her weekend, her chance to cut loose and have fun with the girls, but NO those bitches run off to fuck the first guys that buy them a drink. "I don't need them to have a good time I will find one on my own" she told herself. "Shit, damn shoe" looking down she noticed the buckle of her shoes had come undone again. Bending over she worked on getting it rebuckle, but doing it drunk...

New girl at work

The new girl started at my job recently. We will call her Helen. Now she's not the most attractive looking woman I've ever seen but she has some great features. Nice eyes, looks like a nice set of tits, nice butt. She's smart, funny, easy going and I picked this up only spending a couple hours with her. While training her we talked about our life and how we got to where we are and everything in between. On her third day she came in just like the past few days, nothing out of the ordinary. "Hey...

Picnic Area Fun

I was in Spain by myself & I saw on Squirt there was a good picnic area on the autotavia which was supposed to be a good gay site. It said it was best at night. So having got myself showered I went to find it arriving at dusk so I could see the layout. There were several cars parked up most with just on guy in so I was optamistic. I got out the car & walked round finding were the secluded places were, just the a white van pulled up & guy in work clothes got out & walked in my...

Far Horizons

© Copyright 2004 At thirteen, I was about as sexually frustrated as a young boy could be. My friends and I would go down to the corner drugstore and giggle and point at the pictures in the girlie magazines until the owner finally noticed us and kicked us out. He tried to sound gruff, but when he wasn't looking, every once in a while, I'd catch him smiling, as if remembering his own adolescent years. Once in a while, we'd camp out in somebody's back yard. Invariably, someone would...

Mirror Mirror on the Wall

I’d like to thank Randi and SOL for this opportunity to write something outside my normal oeuvre. I thank Randi for her skilful editing. However, any subsequent errors are mine and I demand the right to claim any such errors as my own! And The Hammersmith Nude Murders aka Jack the Stripper was a real case. The murder weapon was as described in this story. The case was never solved. Danny Flavian was going to die, and it was all his own fault. Not that he actually accepted this fact, but...

Threesome in the Limousine

By Dina PetroMy friend, Natasha and I had just come out of a friend’s birthday party, had a couple of drinks each, we were dressed in nice outfits very sexy too. Natasha being the same age as me mid-twenties by then, my name is Alice, we were hot, sexy, gorgeous pair of girls goofing around town.We were passing by a super luxurious hotel facilities, our eyesight was attracted by a nice, super long Limousine car, colored white parked on the side right there, we looked at it shocked by its...

Sears IslandChapter 19 brutal cold schoolwork and the magic flute

It got brutally cold that January. The temperatures dropped well below zero and stayed there. The gale force winds didn't help much, either. The snow drifted the road closed almost as soon as Mark had it plowed out. We gave it up as a bad job and pulled our heads in. I worried about the LP gas tanks lasting the winter. We turned back all the heaters to fifty degrees and went about in jackets. Heating pads made all our beds comfortably warm. Since the kids were eight years old I'd purchased...

Threesome With My Friend And His Plump Wife

Hi Friends, I am also one of the fans of Indian sex stories. I respect for the people who made such a platform available for us to read and share natural sex stories, I love stories more than porn as it helps me in running my imaginations wild. Although recently I started loving Savita bhabhi comics. I also respect people who in the absence of having a partner satisfy themselves with masturbating reading stories etc instead of doing any ugly crimes like rape. I feel availability of easy porn...

Look But Dont Touch

She swayed into the room atop six-inch platform high-heeled, thigh high patent boots. The boots were worn over black stockings, the tops of which were slightly higher on her thighs, attached to garters that disappeared under panties. She wore her garter belt under the panties so she could pull her panties off for easy access to her pussy without having to remove her garter, stockings, or boots. A deep blue corset covered her midsection, pushing her tits up and making them fuller than her...

Sissy the Redhead Making of a Slut Part I

Part I She was out mowing the lawn again. That little red head across the street. She was probably thirteen or so. Maybe fourteen, and she had long thick curls of deep red hair. The kind that looks dyed, but isn’t. Her titties were just coming in, but they were coming fast. She must be pushing a B cup by now, only she wasn’t wearing a bra that day, just a tight little baby tee that said “Candy” on it that showed off her tight, flat waist. The shorts she had on didn’t hurt in...

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