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.
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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 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,
