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WARNING: This story features a woman pegging a guy’s ass with a strapon and the man eating his own cum. If neither of those two scenarios appeal to you, then you should consider reading another story.
When I moved to my current town about six months ago, I knew no one. I moved here because I was recently divorced and desperate for a job. After almost a year of being unemployed—which was one of the reasons that my now ex-wife left me for one of her coworkers—the local community college in a town a five-hour drive away from where I was living offered me a position as a tenure track English professor. It was tough for me to pull up stakes and move so far away from home, but the compensation package and opportunity to become tenured was too good to turn down—especially since it was the only job offer that I had at the time. Plus, I needed a fresh start in life, and this move to a new town was a perfect way to get it.
I’m an introvert, so it was difficult for me to meet people when I first arrived here. One activity that I do enjoy a lot is running in road races. About two weeks after moving here, I entered a 5K race, and that’s when I met Alisha.
I don’t necessarily believe in love at first sight, but when I first saw Alisha wearing her matching midriff exposing sport top and skin tight compression shorts, I was smitten. Alisha is a very petite lady. She stands at barely over five feet tall, and her slender, well-toned runner’s body barely weighs 100 pounds after eating a bacon cheeseburger. But despite her petite frame, she does have curves in all of the right places. Her breasts are perky little B cups, and her ass looks fantastic filling out a pair of yoga pants.
Alisha also looks younger than her age. I was a very surprised during the awards ceremony after the race when she took first place in the female 30-34 years old category. I could have sworn that she was barely old enough to drink! I guess it just goes to show that good eating and good exercise keeps a lady looking young.
Luckily, I also took first place in my category—male 35-39—which gave me an opportunity to congratulate her on her medal while wearing my own. I was pleased to see that she has a very bubbly and outgoing personality. On second thought, maybe love at first sight does exist.
It took me talking to Alisha after three different races for me to finally find an opening to ask her out on a date. I was nervous because in my eyes, she is so beautiful. I couldn’t believe that she wasn’t already married, or at least had a boyfriend. I was pleasantly surprised when she said that she would go out with me. I did my best to make a good first impression. I took her to a nice restaurant, and during dinner, we flirted and played that whole cat and mouse game with each other. Then I tried to show her that I was cultured by taking her to see a live play at the local theater. We both enjoyed the performance, and we talked about it in the car as I drove her home.
When I took her back to her apartment, she invited me in for “coffee.” Knowing what coffee truly means, I accepted the offer, and after a glass of wine each, she allowed me to seduce her. She gave me one of the best blowjobs that I’ve ever had—better than any my ex-wife ever gave me. As I lowered my head between her firm, muscle-toned thighs, I tasted the sweetest pussy I’ve ever tasted. But nothing could prepare me for how tight her pussy was when I finally slid my cock into it. I assumed that Alisha’s pussy would be tight because she’s such a petite lady.
I may not have the biggest cock in the world, but I’m not ashamed of it. It’s about six and a half inches long, and it’s thick enough to make a woman’s pussy feel full. But when I slid it into Alisha’s tight fuck hole, I felt like it was as large as a porn star’s cock. Alisha’s pussy was so tight that I had to struggle not to come right away. Luckily, I don’t know how, I was able to hold off until I felt her pussy clamp down on my cock as she bit her teeth into my shoulder. I learned at that moment that Alisha is also a squirter as her juices coated my cock, balls, thighs, and the bed sheets. When I felt Alisha’s pussy put a death grip on my cock, I came so hard that I saw stars. It was one of the most satisfying fucks I’ve ever had. Alisha and I fell asleep in each other’s arms, and we had a good morning fuck before I had to go home and get ready for work.
This routine of Alisha and I going out on dates and then fucking each other, either at her place or mine, went on for about five or six weeks. We’d see each other about once or twice during the week. On Saturdays, we would either kartal escort go on a long run or compete in a race, and then spend the rest of the day together doing normal couple things and fucking like rabbits when we were at one of our apartments. I was quite happy with the arrangement.
One thing that Alisha was reluctant to do though, at least at first, was allow me to fuck her in the ass. When running with—or behind—Alisha, I always admire the way that her firm little ass cheeks fill out her spandex shorts. I know from experience that sometimes a woman’s ass looks great in spandex, but then sags a lot when the shorts or the yoga pants come off. This is not true for Alisha. Her ass stays elevated when she’s naked. The cheeks fit nicely into my cupped hands, and they look and feel perfect as I grab them while fucking her doggy style. But if my fingers or my cock strayed too close to her puckered little asshole, then she would swat them away. I really wanted to split those ass cheeks with my cock, but Alisha’s pussy is so tight that I figured that it might be impossible for me to fit my cock into her asshole anyway, so I didn’t push too hard for the anal sex.
One day, though, I did get a little bolder. After a nice date, Alisha bent over in front of me to remove her jeans. Her ass looked so inviting while she was in that bent over position, that I fell to my knees behind her and told her to stay there while I removed her thong. Alisha put her hands on the bed, spread her legs slightly, and stayed put. In my kneeling position, her ass was level with my face. I slowly pulled her thong down, savoring the view. I only pulled her thong down to her knees, and then I moved my face forward, buried it in her pussy, and flicked her clit with my tongue. Alisha moaned in approval. I was in sensory overload because her womanly scent was intoxicating. Her pussy tasted heavenly, her perfect ass was a sight to behold, her ass cheeks just felt natural in my hands, and the sounds of pleasure coming from Alisha told me that I was hitting all of the right buttons. For a few moments, I just savored the moment while I ate Alisha’s pussy.
I could have stayed there in that position forever, but the sight and feel of Alisha’s ass made me want to try something new—just to see how she would react. I put my tongue on her clit again, I ran it up her tasty pussy lips, but instead of stopping at the end of her pussy, I kept going. I ran my tongue up to her puckered asshole, and I started rimming it. I fully expected that Alisha would pull away from me, but she didn’t. Instead, she pushed her ass back towards my tongue. I pulled her ass cheeks apart and flicked my tongue over her hole a few times. When she moaned in pleasure, I hardened my tongue, and I pressed it at the entrance to her asshole. I tried to work my tongue in, but that’s when Alisha stopped me by gently pushing my head back.
I immediately sputtered and started apologizing. Before I got too carried away with my apology, though, Alisha shushed me my putting a delicate finger over my lips.
“It’s okay,” she said. “I like what you’re doing.”
I started to move my face back to her ass again, but she stopped me.
“Would you really like to fuck me in the ass?” She asked.
I was surprised. She had never shown any interest in anal play before that moment, and then, out of the blue, she just straight out asked me that question. But, now that the question had been asked, I had to be honest.
“Oh yes,” I breathed.
Alisha got a wicked little smile on her face. “I’ll let you,” she said, “but only if you let me do something.”
Uh oh, I thought. Where is this going? But, my curiosity got the better of me. And her ass looked so inviting. I had to know what the conditions for splitting those perfect cheeks with my cock would be. “What would you like to do?”
Alisha turned around, bent over, and gave me a deep kiss on the lips. She pulled back, and said,
“I want to fuck you in the ass too.”
“What?” I said.
She looked me right in the eyes. “With a strap on.”
“Whoa! Whoa!” I said.
Alisha pulled away from me. “See? I knew you would act that way.”
“Of course I would,” I protested, “I’m not gay.”
“I know you’re not,” she said. “But letting me fuck you in the ass with a strap on won’t make you gay.”
“What?!” I didn’t know what else to say. Alisha took advantage of my befuddlement.
“Come on,” she said. “Let me do it.”
I hesitated. I had never had anything other than my own finger up my ass before. Would giving in to her demand really be such a bad thing?
“Let maltepe escort bayan me do it, and you can have this.” She stood up, turned around, and moved her tight little ass towards me. Without hesitation, I buried my face in her ass and started licking up and down the crack of it, pausing to run my tongue around her puckered hole. Alisha allowed me to do this for a few minutes. I got into a good rhythm, circling her puckered hole with my tongue, and then hardening it and trying to poke it into her back door. Her asshole was too tight for my tongue to penetrate, but I didn’t mind. Then, once Alisha knew that she had me, she pushed my head back, looked into my eyes, and asked,
“Do we have a deal?”
I couldn’t say no at that point. I just nodded my head.
Alisha squealed with delight, and jumped off of the bed. She opened her nightstand, and pulled out her strap on. It was about six inches in length, and it was pink. She put it on, and then stood in front of me.
The sight that stood before me was beautiful! Alisha’s angelic face. Her long, kissable neck. Her perky little B cup boobs, with the nipples as hard as diamonds. Her flat belly. But, where her shaved pussy would normally be, a pink, six-inch cock stuck out above her slender, well-toned legs. It seemed like a strange sight, yet Alisha was still able to turn me on just by standing there like that. She only posed in front of me for a few seconds, but they were breath-taking seconds. Then, she reached into her nightstand, and pulled out a tube of lubricant.
“Turn around,” she said.
Without realizing it, I found myself obeying her order. I spun around and faced away from her. Then, I felt her hands on my ass cheeks. Gently, she spread them, and then, she did something that I wasn’t expecting. She pressed her lips to my butt and started kissing it. Slowly, she went from one ass cheek to the next, and then she ran her tongue from my taint to my asshole.
I had never had anyone lick my asshole before. My ex-wife was too much of a prude to do it. But I really enjoyed the way that Alisha was working her tongue on my butthole. I relished in this new sensation for a couple of minutes as I experienced something that I never thought I would experience. Then, I was jolted for a moment as I felt something cold on my butthole. It was the lubricant. Then I felt Alisha’s finger pushing at my asshole.
I inhaled sharply. “Just relax,” Alisha said. I tried, but since I hadn’t anything other than my own finger up there in my lifetime, I was a little nervous. Alisha said, “Take a deep breath.” I inhaled deeply. “Now exhale deeply.” I did, and as I was letting my breath escape from my lungs, Alisha’s finger popped into my ass.
I was surprised. I thought that there would be pain when she poked me. There was none. I won’t say that it felt good either; it just felt like there was something in my ass, and there was.
Slowly, she moved her finger in and out of my butt. She made sure to brush her fingertip over my prostate with every in and out. I felt my cock stirring. After a few moments, I felt a second finger go in. It was a little more uncomfortable, but soon I adjusted to that too. My cock got harder.
Before long, Alisha removed her fingers from my ass. I was slightly disappointed because the prostate massage she was giving me felt good, but then, I felt some hard, rubbery thing being lined up with my asshole. I knew that the moment of truth had come.
“Just relax” Alisha said as she started to gently press her fake cock against my back door. Instead of relaxing, I tensed up. “Take a deep breath,” she said. I did as I was told. Then, she told me to exhale. I did, and the next thing I knew, I felt a sharp stinging sensation in my asshole as the head of Alisha’s dildo popped past my sphincter. That one hurt! I involuntarily yelped in pain, and tears started to squeeze out of my eyes.
“It’s okay, Babe,” Alisha said to me. “The worst part is over.”
She stayed perfectly still while I adjusted to the intrusion in my ass. Slowly, the pain receded, and I looked over my shoulder at Alisha and nodded.
She placed her hands on my hips, and slowly fed the dildo into my ass.
Sometimes, she would pull back slightly, and then push forward again, going just a little farther with each push. Eventually, I felt the full length of the strapon as she got it all inside of me. I couldn’t believe that I took it all. Then, Alisha pulled back, and pushed in again.
She built up a steady rhythm. I had never felt anything like what I was feeling in that moment before. I could hear the escort pendik sound of flesh slapping as she drilled my ass.
I don’t know why, but once I had gotten use to the fake cock in my ass, I said, “Faster.” Alisha complied.
As Alisha kept fucking me in the ass, I looked at my cock. I couldn’t believe how aroused I was. It was swollen bigger than I had ever seen it before, and it was an angry red color. The sensation of being fucked in the ass by Alisha was amazing. I never knew that anything could feel that good. I was beginning to really enjoy myself when Alisha suddenly stopped.
I whimpered a little when Alisha pulled her cock out of me.
“On your back,” she said. Obediently, I rolled over and lay on my back.
Alisha spread my legs and scooted up closer to me. “Pull your knees towards your chest.” I did as I was told. Pulling my knees up allowed Alisha to line her rubber cock up perfectly with my asshole. This time, I didn’t feel any pain when she pushed it in. I guess the thorough fucking that she had given me in the doggy position really opened my ass up for her cock.
Slowly, she worked her strap on into my ass again. Then, she started thrusting harder. I had never thought that I’d ever experience anything like this. Here was this beautiful woman, with a pretty face and perky tits, gazing into my eyes while the lower half of her body was pounding a rubber cock into my asshole. It was amazing, and my cock was as hard as a steel pole from the through fucking she was giving me.
I pulled her face to me and gave her a deep kiss. In and out. In and out. Her thrusting never slowed down.
When we broke our kiss, Alisha spit into her hand, and then started stroking my cock. Once she started jerking me, I knew that I wasn’t going to last very much longer.
Luckily, Alisha was close too. I saw her face scrunch up in that beautiful expression she has when she’s orgasming. She let out a primal scream. Her body started shaking as she was pumping her strap on in and out of me. Her shaking caused the strapon to start vibrating rapidly in my ass. I felt like she was using a vibrator on me. The only thing that stopped me from cumming right then was that Alisha had such a tight grip on my cock as she was riding out her own orgasm.
After what seemed like forever, she finally started breathing normally again. Once she had come down from her high, she slowly pumped her fake cock in and out of my butt while her hand stroked my real cock. It only took about three or four strokes before I tensed up and my cock unleashed one of the biggest loads of cum I think it’s ever released. The first two shots were so powerful that they landed on my face, in my hair, and splashed on the headboard behind me. Rope after rope of creamy semen splashed on my stomach, chest, and neck. By the time my cock was finished shooting its load, I was drenched in my own cum. All I could do was lay on my back and gasp as I tried to catch my breath. I was exhausted.
Slowly, Alisha pulled her cock out of my ass. I could feel my gaping asshole starting to close up again.
Alisha sucked on my cock a little, making sure to suck the last of the cum out. She then started using her tongue to lick up the cum on my stomach. I wasn’t totally surprised by this. She always swallows my cum when she gives me oral. She says that she really likes the way my cum tastes.
Slowly, Alisha worked her way up my body, licking up the massive load that I had sprayed onto myself. Then, after she had licked my cum off of my neck and chin, she did something that did surprise me. She kissed me on the mouth, forced my mouth open with her tongue, and started feeding me my own cum. I was shocked because she had never done anything like that before! Alisha really was pushing boundaries that day.
At first, I tried to pull back. I’ve tasted my own cum before, but always by accident. Sometimes when I masturbate to porn, I cum so hard that the cum hits me in the mouth. But I had never tasted a mouth full of my own cum before. I wasn’t sure I was going to like this. Alisha wasn’t taking no for an answer though. She used her tongue to drip cum in my mouth, and then to scoop it back out again. After about half a minute of this, Alisha dumped some of the cum into my mouth, and then she pulled her face back.
“Swallow it,” she said. And I did.
I must confess, while I didn’t love the taste of my cum, I didn’t hate it either. It was a bit slimy with some saltiness to it. I decided that if Alisha was going to make feeding my cum to me a regular part of our sex life, then I could live with it.
Alisha laid down next to me and draped her arm over my chest. At first, I thought that she was going to call it a night right then, but she wasn’t. We had made an agreement, and she was just letting us take a break before she fulfilled her end of the bargain.
TO BE CONTINUED
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