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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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Daddy's IntroThis is just a roleplay between me and another ;) EnjoyINTRO OF DADDYSugar_DaddyHey slut!Having a hot time tonight?Big_titty_fuckerno just home and horny for a big dick daddy to fuck meSugar_DaddyLove your pics of you in the "boing boing" topyour tits are so big the bikini doesn't quite cover them!Very sexy!Big_titty_fuckerhaha thanks. does daddy like how big my tits have gotten for him?Sugar_DaddyOh yeah, I love it!love to put my big cock between themlove to fuck your big...

From Duchess to Concubine

Duchess Mona of Remnia paced the floor of her private apartment in the grand castle. She swept back her long brown hair and then released it. She took a look in the mirror and saw a lovely, tall, blue eyed woman with a porcelain countenance and a stunning figure. Even at a time like this she could remain focused on looking her best. Behind the bowed lips and strong chin, however, she grieved. From what she could tell the news of the battle was not good. The last messenger informed the palace...

Stockholm Syndrome Part 2

It took me several hours of shopping before I took pity on the dwarfs and we finished the drive. The rented house was lovely, right on the beach with terrific views. I had my own suite of rooms including a small sitting room, bedroom and very luxurious bathroom. I freshened up and put on cardigan sweater and a khaki skirt, and came down to the main living room and said to the dwarfs "I know a great restaurant over in Perkin's Cove, who's up for seafood?" Nobody jumped at the chance,...

Kinky Kirsty 2 Home

I told them to get ready as dinner was ready, showed them which seats to sit at, and then said wine is there and probably still cold enough. We all sat around and ate dinner and had a couple of glasses each. Kirsty then said, “would you like me to clear the table?” Ross replied, “no I can do that” “Thanks” I said, “I would like Kirsty to tell me about the day you two have had”. Looking out of the corner of my eye, I saw Kirsty’s face drop, she swallowed hard and physically squirmed in her...

Kavlas

Kavlas, king of the Dardrics, was happy today Kavlas, king of the Dardrics, was happy today. News from the frontline had reached him, that the long running war with the Iceans was over. Their warrior queen had surrended to his forces, and was being transported back to his capital in chains. It had only been a matter of time of course. The Iceans were fools, allowing women equal status with men in their society. How could any army in which women fought alongside the men in equal numbers,...

Italian Lessons

It was my daughters birthday and I had met my ex wife and the two girls in a lovely Italian restaurant that someone suggested to her. Neutral ground I had thought, but things hadn’t been too difficult between us and the girls had both enjoyed it. It was late on and the three of them had gone home across town to where then three of them lived. I was sitting in the subdued light of the booth, in the now empty restaurant nursing the end of a cappuccino and brandy, awaiting the arrival of the bill....

How I Became the Family Slut Part 4

"Goddammit, Sweet Muffin, you've got the tightest pussy I ever fucked!” Those were the first words out of my daddy's mouth when his hard cock penetrated my pussy for the very first time.At this point in my story I was just a couple of months past my sixteenth birthday. I was five feet tall, skinny, had hardly any tits to speak of, but I had a small waist, a cute butt and a flaring set of hips that I was just learning how to use. I had curly red hair, freckles, and braces on my teeth. I was...

Incest

Holly Jolley Christmas Pt 1 of 2

I was fruitlessly looking at hotels on my tablet when the text message came in. When I heard the alert, I grabbed the phone and saw the message was from my sister.“Mom wants 2 know when ur coming home?” the message read.“Not sure. I’m trying to figure a couple of things out,” I typed in response. A moment after I hit send, my phone started ringing. It was my sister again. She didn’t even give me a chance to say anything.“You text too slow,” Holly teased.“Pardon me for spelling, Sissy.”I...

Incest

A Ride in the Bush

It was a good day for hitting the pedals of the bike, there was a light breeze but no wind, it was warm but not hot, a perfect day. Barry manoeuvred his machine from where it was kept in his workroom. It kept the other machines company, it was a bit crowded but the bike was a little more up to date than his old one, which was housed under a tarp, up against the side fence. The idea for this days ride was to try and ride around one of the outer suburbs and hopefully remember the track. He had...

Taking the Risk Ch 14

Thank you to all those who have left messages, and as I write I am taking your suggestions to heart, I hope you take Misha and Froo to yours/ This is a slow, romantic build between two lovers who have found each other. Character based, the story is about people who care and want to give pleasure to each other, in all aspects of their lives. But to love someone, you must learn to love yourself. If you like romantic stories please enjoy, and please give feedback, as the ending is not yet...

Cocktease

‘Cocktease,’ he had called her, out of earshot of her husband and his wife. In retrospect, perhaps she had overdone it a bit from time to time. A flash of lace now and again, a breast resting snugly against his arm as she poured him another glass of wine, a little parting of the lips and quick swish of the tongue as they said goodnight following visits. Truth be told, these had been more for herself than to titillate David. That he may have been frustrated by these events had not really...

The Newtons

Part Five He liked it when I dressed up for him and he was instantly aroused and had me over the kitchen table. Lifting up my dress and fucking me without even stopping to put on a condom. He had me again in bed that night and I loved having his strong arms about me which made me go all soft and gooey. Work was the same over the next fortnight and the sex was never better with Miki, fucking and sucking each other nearly every night. I had told Miki of what went on between Christiana and...

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