My Top Ten Sexual Encounters

When we got inside my hotel room I turned Carol toward me and French kissed her plunging my tongue in her mouth. She kissed me back with enthusiasm and I steered her over toward the bed. I lowered the top of Carol's dress to her waist and bared her flat chest. Carol had no boobs but she had hard little nipples that stuck out about an inch. I sucked on her nipples and she loved it.

Carol called out to me as I was sucking her nipples. "If you want boobs I haven't got them."

I stopped sucking her nipples long enough to reply, "Don't worry I am a leg and ass man. I am not into big boobs."

Carol was thrilled and she couldn't wait to get my cock in her pussy. I went back to sucking her nipples and then I finished undressing her. The dress fell around her ankles and she flopped back on the bed. I eased her pantyhose off her and then her panties. Carol had a cute pussy with a little tuft of brown hair above the opening. She was dripping wet when I slid my tongue across her labia and then worked it into her sweet passage. Carol stiffened and came with a mild orgasm as I slipped my tongue in and searched for her hooded clit. Carol screamed out loud when my tongue touched her clit. Then I pushed her legs further apart and spread her lips open with my fingers. Her erect clit was standing straight out and I bit it lightly with my teeth. Carol jumped with pleasure and moaned loudly. I continued to lick and nibble her clit until she lost it and sprayed my face with her female love juice. Carol tired to push me away but I held her hands firmly and pressed my tongue into her twat. Soon she was pleading out loud for me to stop, that she couldn't take it any longer.

I stood up and removed all of my clothes as Carol lay on the bed recuperating. Carol looked at my hard cock as I approached her and I could see she was pleased. I moved between her legs and slid my cock in her pussy. She was a little snugger than I thought she might be and I was happy that she could feel my cock against her vaginal walls. I started fucking her slowly but then I needed to cum and I picked up the pace. Carol fucked back at me throwing her pussy up at me as I plunged my cock deep in her hole. We were both fucking frantically now and racing toward our mutual orgasm. I was out of control as my seed flew out of my cock and splashed against Carol's vaginal walls and deep into her pussy. She strained as she too had another intense orgasm and she worked to keep her clit in contact with my cock. We started to move slower and regain our composure. We were dripping wet with perspiration.

The two of us rested in each other's arms and I stroked Carol's body. I loved the touch of her skin, her shapely legs and curvy sexy bottom. Carol loved to have her pussy played with constantly, then she would get aroused and either she would mount me or I would mount her and then we would fuck again until she orgasmed. Carol orgasmed countless times that night and she seemed insatiable. After my third ejaculation, which was always a stretch for me, I had to resort to my fingers and tongue. We eventually fell asleep in each other's arms.

In the morning Carol was ready to go again and I was thankful for my early morning piss hard-on. I could always last a long time before I took my first piss in the morning so I was able to fuck Carol through multiple orgasms satisfying her needs. I got up and left her lying on the bed drained from the intensity of her climax and I went to the bathroom to relieve myself. When I returned to the bedroom Carol was playing with her pussy again and I was ready to get off myself. I crawled between her legs and slipped my cock back in to her wet pussy and we fucked until we both came again. I shot wads of cum into her that morning and surprised myself with the volume and force of my ejaculation. We then showered, dressed, ate breakfast and then departed the hotel. Carol went to her office and I flew back to Chicago. Carol gave me her phone number and asked me to call her the next time I was in Detroit.

I continued to see Carol each time I returned to the Detroit area and our sex was always intense, exhausting and fulfilling. One day I received a call in the Chicago office from Carol that her company was downsizing and her boss's position had been eliminated. As a result her position was also eliminated. She wanted to know if I knew of any positions open with any of my clients. The timing couldn't have been better as my secretary told me that she was leaving and I would then be looking for a replacement. I asked Carol if she would be interested in working for me in Chicago and she couldn't say yes fast enough. She was ecstatic and told me that she could be in Chicago in two weeks.

Carol came to town and stayed with me for a few weeks before we got her set up with her own apartment. I had to travel during that time as well so it worked out for both of us. The first weekend together we didn't leave my condo. We had continuous sex and stayed naked for the majority of the time. Carol loved being naked and displaying her lithe body. Even when we watched television or a movie she wanted her pussy played with constantly. It was that weekend that I also started playing with her ass.

Carol liked her ass fondled and the anal intrusion of my finger. I always greased her asshole with lube and then fingered her ass as I played with her pussy. I fingered her asshole every time that I ate her pussy. I also fingered her bum when I fucked her doggy style. One time when we showered I washed Carol's ass thoroughly pushing my soapy fingers deep in rectum. After our shower I had Carol get on the bed on all fours and I licked her pussy from behind. Then I moved my tongue up to her nether hole and teased her with the tip. I continued to lick and probe both her pussy and asshole with my tongue and Carol went absolutely wild. She had one of the most intense orgasms I ever saw her have just from the cunninglus and anal stimulation.

I told Carol about Pam and how that was my first time rimming anyone. Carol was intrigued with Pam's passion for anal sex and she admitted that she had often thought about it but had never tried it. Carol told me that she trusted me and that if I wanted to try it with her that she would. Carol has a perfect bubble ass for butt fucking as it is round and smooth and perfectly contoured for her lithe body. I told Carol that we would work up to it and that I would introduce her to anal toys and stimulation that would loosen her up and bring her pleasure. I really wanted to fuck her ass but I did not want to injure her or scare her away.

As Carol settled in to her new job we continued to have torrid sex and I introduced her to more and more anal pleasures. I kept adding toys to our relationship and the ones she enjoyed the most were the anal beads and a vibrating dildo. The first time we used the anal beads I thought she was going to pass out. I ate her pussy and I popped one bead out of her ass at a time as she orgasmed until all five beads were removed. Carol screamed out loud and her body went into convulsions with the intensity of her climax. Carol also loved the vibrating dildo in her ass as I fucked her pussy doggy style. As she became accustomed to the beads we increased the size of them and we would keep increasing the size each time she became comfortable with the intrusion. We had reached the point were we felt she was ready for my cock.

That evening I fucked Carol and ate her pussy until she had multiple orgasms and she was totally relaxed. I rolled her over and had her kneel on all fours on the bed. I used my fingers to lubricate her ass putting plenty of the slick substance in her asshole. Carol cooed as I fingered both her asshole and her pussy simultaneously. I placed my hand in the small of her back and pushed lightly so that Carol arched her back and accentuated her curvy ass. I was so ready to fuck her ass my cock was harder than ever and throbbing in anticipation of taking her anal cherry.

Carol felt the thick head of my cock between her rounded buttocks and just outside her nether hole. She knew that it was finally about to happen and she felt her stomach turn with the thought of committing such a depraved act. I put an ample amount of lube on my cock and then added my saliva to it making it as slippery as possible. Once I was satisfied that my cock head was slick enough I introduced it to the tight ring of Carol's anus. Carol looked back over her shoulder at me as she felt me pushing my cock against that intimate part of her body.

"Please go easy, be gentle," she reminded me.

I slowly pressed against her tight opening and noticed that Carol was holding her breath. I told her to relax and breathe deeply as I continued pressing forward. Carol felt the initial thrill of her sphincter being forced open by my thick cock and her first response was to try and avoid the anal invasion. I held her hips and I continued to push forward past her resisting body. Carol's mouth gaped open and she grasped the bed sheets in both hands as my cock head cleared her sphincter and lodged in her anal channel. Carol unintentionally flinched and caused more of my cock to slide inside. She cried out.

"Are you okay?" I asked.

Carol nodded and then she once again reminded me to go slow. I gave her a few seconds to recover and then pressed forward again and her flower opened up for me. She just needed a few minutes to get used the unfamiliar sensation of being so filled from behind. Carol then responded unexpectedly as she accepted my cock in her ass. So pushed her butt back toward me and then moved forward. She did this for awhile and it seemed as if she were accepting and rejecting my cock at the same time. Finally my cock was buried to the hilt in her ass and we began moving together. I felt my balls slap against her pussy each time I thrust into her hot ass.

"Oh, this is so sexy. It feels so good but I feel dirty at the same time. If my parents could only see their precious daughter now," Carol murmured.

Carol had been raised by very strict parents and she had always been taught that pre-marital sex was taboo and dirty. I too wondered what her parents would say if they could see their daughter with a cock in her ass. Carol's lust took over and she rolled her ass in tiny circles as she was consumed with her first anal fuck. I looked down at her firm buttocks and I marveled at the way my thick shaft stretched her nether hole. I tired to imagine Carol's parents, whom I had never met, standing on either side of her watching as her asshole opened and contracted around my cock.

Carol reached between her legs and into her puffy cunt. Her juice was oozing from it and she rubbed her stiff and aroused clit. I picked up the pace and began to fuck Carol's ass with steady full thrusts. She gasped at the new almost unbearable sensation surging through her rectum. There was no pain now but just a glorious feeling of being stuffed with cock. She felt full and a little bloated but the pain had disappeared quickly and the bloated feeling was gone also. Carol loved the taboo feeling of being filled with cock in her ass. The thought of this forbidden act along with her clitoral stimulation pushed Carol closer to yet another climax.

I was trying to hold off my threatening ejaculation as Carol's movements intensified with her pending orgasm. We were both perspiring and I held to Carol's shapely buttocks as I slowed my pace slightly in an effort to slow my eruption. Carol groaned loudly as her head dipped down to look between her legs and she pushed back in an effort to get more of my cock in her.

"Oh Walt, fuck me. Fuck me in my ass, it's so good so wicked, I love it," Carol cried out.

Carol was going wild with my cock in her ass and I had never seen anyone take to anal intercourse with such abandon for the first time. Carol balanced herself on both hands as she thrust backward impaling her ass on my thick cock. I knew that I could not hold out much longer. I reached around with one hand and found Carol's pussy and engorged clit. With the other hand I squeezed the rock hard nipples sticking out from her flat chest. Her clit throbbed as it clamored for attention and her pussy clenched my fingers as it released her warm love juice. The points of her nipples were excited beyond desire and my cock was clamped in her well stuffed bottom.

Carol was out of control as all she knew at this point was that she was being fucked up the ass with a very thick cock and it felt fantastic. She was on the verge of her most intense orgasm ever and she struggled frantically seeking her climax. A few more seconds of rubbing her stiff clit sent Carol into a mind blowing orgasm. Her body stiffened and then spasmed out of control as she moaned loudly and struggled to breathe. The intensity of her climax was too much for me and I grunted as I shot my spunk into her forbidden tunnel. Carol's eyes flew open in surprise as she felt my hot thick semen rush into her rectum and splash off her bowels. Her face was pure ecstasy as she turned to look at me as my cock continued to spurt its sticky fluid up into her.

"Give it to me, cum in my ass, oh I can feel it. it's so good, so nasty," Carol cooed as she was overcome with passion

Carol fell forward on the bed as I continued to marvel at the beautiful ass that I had just deflowered. As she lay before me she clenched and unclenched her ass muscles causing cum to ooze out of her asshole. It looked like a small spring as the semen intermittently bubbled up and trickled out of her ass between her ass cheeks and over her puffy pussy lips. I stayed hard and stroked my cock as the last tiny drops landed on her ass. I then realized that I was going to stay hard and I decided to try and fuck her ass again.

I told Carol that I wanted to fuck her ass again and in an almost business like fashion she pushed her self back up on her knees. She turned her head to the side and smiled at me waiting for the second penetration. I pushed my still erect slippery cock into Carol's now gooey asshole. Carol felt her sphincter being stretched again but this time she enjoyed the sensation of her ass being filled with my thick cock. As I pushed inside her my spunk from the previous ejaculation was squelched almost obscenely with my cock. My previous deposit squeezed out around my shaft and oozed from Carol's asshole running down between her buttocks and plopping on the bed sheets.

Carol was an extremely hot woman and her fucking technique was incredible. I stayed crouched behind her and placed my hands back on her hips as I fed my long thick cock deep into Carol's accommodating back passage for a second time. Carol pushed her hips back at me and her bodies slapped loudly together.

"Yes, yes, oh I love it. Fuck my ass with your hot cock," Carol yelled to me and then she cried out, "Make me cum again fuck my ass with that big cock."

As before Carol lowered her head to the bed and turned it to the side as she grasped the bed sheets. But this time she grabbed the sheet in the thrones of passion and not because of apprehension. I could feel her taut muscles massaging my shaft in her ass as I held on to her slim waist and I caressed her curvy firm ass cheeks. Her sphincter grabbed the base of my cock as she worked her lithe athletic body. Carol was an incredible sex partner who had just turned into a fantastic ass fuck. I knew that I was getting close to losing it again as Carol manipulated my pecker with her undulations and muscles and that I would soon be adding more semen to join my previous load in her ass.

Carol had her hand back on her clit and rubbed herself frantically as she had another violent orgasm thrashing and panting wildly. I felt my seed travel along my scrotum and then spurt into the recesses of her ass. Carol felt the second ejaculation shoot into her bottom and she wallowed in the feeling of the warm liquid once again soothing her ravaged ass. Carol squeezed her ass muscles extracting every drop of cum from my cock until I went soft and slipped from her hot gooey ass with an audible pop. Carol collapsed face down on the bed and savored the moment. She knew now that she was hooked on anal sex and that she could expect to be ass fucked regularly from now on. I flopped next to her and held her to me as we kissed and rested.

"I never thought that I could get so turned on from anal sex. It was incredible I felt like I would never stop cumming. The feeling of your hot semen shooting into my ass was unbelievable. I never expected it to feel so good just from being so full," Carol murmured as we lay together.

"I am so glad that you liked it as you know I loved fucking your ass," I replied.

Carol then cuddled back up to me and we dozed in each other's arms. Later we had vaginal sex as Carol rode my cock until she came and collapsed on me as I shot another wad in her pussy this time.

For the next two years Carol and I had a very steamy relationship. She was a very passionate woman who wanted nothing more from our relationship other than very hot sex. Our company was sold and I moved on to another job and Carol returned to Detroit and pursued her career back in her home town. I never saw Carol again but it had been a marvelous two plus years together.

NUMBER 6 -- SHERRY

My best friend Ken and I went skiing for a week every year in Colorado. In 1983 we went to Aspen and stayed in a condo near Snowmass. Ken would always invite some girl that he had fucked before to join him on the trip. This year a woman named Toni showed up the second day that we were there. Toni was nice enough even though she seemed a little shy. I assumed she was slightly embarrassed that I was in the other bedroom while Ken was banging her at night.

Toni was a decent skier and she didn't hold us back. The three of us enjoyed our day on the slopes and our Après Ski. One day we stopped at one bar in Snowmass and there was a really good band there. That's when I met Sherry. She was standing alone near the bar when I asked her to dance. She smiled and accepted and we hit the dance floor and stayed out for five songs.

"I really need to rest a minute," Sherry told me after the fifth song.

"Sure, would you like to join us?" I asked pointing to the table we were sitting.

Sherry accepted the invitation and joined Ken, Toni and I at the table. Introductions were made and we enjoyed the rest of the afternoon together. Sherry was staying at Snowmass for two days and then heading up to Vail to see some friends there. Sherry was a strawberry blonde with a solid figure. She was about 5'6" and I guessed about 140 pounds. She was solid as a rock and had big tits. Her hips and thighs were full but you could tell she was in shape.

The three of us closed the Après Ski bar and then agreed to ski together tomorrow. Sherry said goodnight to us and that she would see us tomorrow. Ken, Toni and I went to dinner and then returned to our condo. It didn't take long for Ken and Toni to go to their bedroom and then I decided to watch TV in my bedroom.

The next day the four of us skied together and had a great time. Sherry was a very accomplished skier and was probably the best of the four of us. After skiing we all showered dressed and went to dinner in Aspen. Following dinner we found a place to dance and party and we had a good time although there was something funny about Toni that day. I sensed that Toni was jealous of Sherry being a better skier and dancer. It's funny how women can get that way at times.

The four of us went back to our condo where Sherry had left her car. I invited Sherry in and I spotted the look of disdain on Toni's face. Sherry accepted and came in for a nightcap. Toni seemed uncomfortable with Sherry in the room so she said goodnight and went into the bedroom. Ken followed her shortly leaving Sherry and me together. We sat on the sofa together with our feet up on the coffee table looking at the fire. It was a romantic setting and Sherry cuddled up to me. I put my arm around her and soon we were kissing and petting. I started to take of her sweater but she stopped me.