Wine, yoga, and my first anal experience [MF]

I have wanted to share this for years, so I am sorry if this is long.

Its 2015. I am a senior at university in a predominantly female dominated major. My class is small, the program itself is a subset of a larger college and there is myself with 14 young women, all ages 20-24. I was the token guy, however I am straight (some of the girls assumed I was gay in the beginning…just because I was the only guy). Most of the girls were in relationships. There were a few single girls there though. One girl in particular caught my eye from day one; lets call her Cara.

Cara and I quickly became partners for everything. We always seemed to find ourselves working on projects, carpooling to our rotation sites, or hanging out on campus. It honestly mostly happened by coincidence, but we started to get to know each other. She started to come over to my apartment infrequently, mostly to work on projects or school related stuff. She was single and I recently got out of a long-term relationship just before this program started. It was starting to be evident that there was sexual tension…we started to get “innocently” physical at times; arm touching, hip-bumping, wayyyy drawn-out hugs, “fuck me” eyes. You know, basically everything other than sexual moves. We were in such a small group of students where everyone knew each other and we didn’t want it to get weird. As time went by, I started to essentially lose my mind. Her body was perfect to me; cute face, probably B cup breasts, and an ass that I was obsessed with. She would always wear these skintight leggings which showed her toned legs and thick ass. I knew eventually we were going to take things to the physical level…there was just too much tension and too many opportunities to take it further.

One night in April, myself and 2 of my classmates meet at Cara’s apartment to work on a project. It was about 11pm and we were finishing up. Wine was flowing (these girls loved their wine) all night, and needless to say 3 of us were feeling pretty good while the 4th classmate was sober to drive. While we were just relaxing, Cara went to take a shower because she had apparently done yoga earlier before we all met up. After her shower, which was about 20 minutes, she came out in a loose tee shirt and those beloved skintight leggings. She took a pretty big “sip” from her wine glass and sat next to me on her couch. We start bullshitting, and eventually get into the topic of exercise and yoga when Cara stands up and walks to the middle of the room. “Yoga is great…it helped my flexibility sooo much…I can actually squat now!” She shuffles over and stands about 2 feet in front of me, and then she starts doing air squats. Within seconds, I was fixated on her ass going up and down, up and down. I could definitely feel myself starting to get hard. She finishes her little “workout” and laughs while turning to me and my classmates and fumbles to the floor grabbing her hamstrings. At this point, I had a pillow and small blanket over me which thankfully covered my growing boner. My other classmates looked at each other and did the whole “oh boy look at the time, we better get going…Jen can’t drive herself!” I think they knew what was going on. Or…they were just weirded out.

After Cara let them out, she went to “get her laptop charger” in her bedroom for a minute or so. When she returns, we make some awkward small talk. I was feeling tipsy and confident, so I asked her, “what other moves did you learn at Yoga?” She looked at me, perplexed, and said, “well there is always the downward dog!” She ties her tee shirt in a front knot, exposing her belly, and hikes up her leggings. She faced away from me and got into position. At this point, I am staring at her ass trying so hard to imagine what is under skintight leggings; I can barely make out the outline of her pussy through them. She stands up and smiles at me. We looked at each other silently for about 5 seconds (which felt like 5 minutes…), and I asked her “what else do you want to show me?” She smirked, paused for a few seconds, walked over to me and straddled me on the couch. “I thought you were never going to ask,” she whispered into my ear. At this point we both seemed to realize what each of us wanted. I pulled her close and kissed her, softly at first, but quickly more carnal. Our hands were all over each other. She looked down and pulled away the pillow, exposing my bulge through my jeans. She slowly started to run her hands over my cock through my jeans while slowly unzipping them as our lips were locked together. I was preoccupied with grasping her supple ass. With my zipper undone and cock begging to be free, she tells me to get up. I push her up and away from me; her leggings have such an inviting wet spot around her pussy.

With my jeans off, my cock is fully erect. I am about 6’4″ tall with about a 6″ cock, and she is about 5’7″ for imagery sake. My boxer briefs could barely contain it. Cara slides out of her tee shirt giving me access to her perky little breasts. I start to kiss and lick her breasts as she takes my briefs off. I reach down and start to peel off her leggings. No panties as I expected. Her pussy was shaved and so, so tight. Standing toward each other, she started to stroke me, and I returned the favor by running my fingers over her soaking wet pussy, softly teasing her clit. I sit down on the couch and she straddles me again, her pussy resting on the shaft of my cock. I paused, and a sense of dread came over me. I didn’t have a condom with me, I wasn’t expecting this tonight. I look at her and say, “Cara, I don’t have a condom on me. I can go to CVS down the road..” She puts her finger on my lips and smirks. “Well, I guess we’ll make it work…don’t worry, I’m on the pill.” (yes, I know stupid me, but whatever…there was no turning back). She adjusts herself so I am about an inch inside her. She softly gasps, and slowly slides down my shaft. She is so warm, tight, incredibly wet. I couldn’t believe it. As she starts to ride me, I can’t keep my hands off her ass. I lick my finger and reach down to her asshole, softly pressing on it and massaging the rim. She moans and whimpers a bit, picking up the pace. Her asshole is so tight, and I press a little harder, barely getting the tip of my finger in. She looks at me and asks if I like fingering her ass. “I fucking love it.” I get more ambitious and take my finger out, lick it to my last knuckle, and slowly press back in deeper this time. I pushed ever so softly to try and not cause any pain, listening to her soft whimpers as I pushed farther in. I can feel her start to twitch, then spasm, and finally that surge of wetness in her pussy. She threw herself on my chest and let out a primal moan as her pussy was clamped firmly on my cock. Her face and torso are cherry red. It was a miracle I lasted during that, 30 seconds longer and I was going to explode. She gets up off me, her pussy dripping all over me, and walks to get a glass of water. At that point, fixated on her ass as she walked away, I had this urge to fulfill my fantasy. “Cara, I want to fuck your ass.” She smiled at me. “Good, I want you to fuck my ass too.”

I had never done anal before. I almost exclusively masturbated to anal porn; it was easily my greatest fetish/fantasy. Cara, unknown to me at the time, did like anal and regularly used her dildos and wore plugs. She took my hand and lead me to her bed. “In the side drawer, get the lube.” She got in doggy position as I liberally rubbed lube on my cock. “Are you sure?”, I asked. “God yes, get over here” she playfully growled. I stood by the edge of the bed and slowly rubbed the head of my cock around her asshole. I could see her smiling and enjoying the tease. I slowly pushed in and Cara let out a small gasp and moan. I was nervous of hurting her or getting “messy,” so I went slow for a couple minutes, feeling every inch of her ass, slowly going deeper and deeper. Her asshole was so tight, and the sensation of being in her ass was unbelievable. Just the taboo around it was intoxicating. After I got more comfortable, I started to go a bit faster and was met with Cara moaning and panting. I could feel myself starting to get to the point of where I couldn’t handle it. She reached around and starts to play with her clit. “God keep going, I am going to cum, please babe go harder,” she begged me. I could feel how wet she was as my balls slapped her pussy. I started to thrust harder and faster, her asshole gripping my cock as it penetrated her. Her back arched and she grabbed for her pillow. Face buried, she moans and lets out a high-pitched, yet muffled, yell. Not 5 seconds later, I start to lose feeling in my legs. My balls seemingly curled up into me, and I almost convulsed. I unload myself into her ass, which seemed to last for 20 seconds. Almost 6 months of pent-up sexual frustration spilled out of my cock into her. Pump after pump, my cock so incredibly sensitive, I keep pushing more and more of my seed into her. She slides down to her side, my cock still pulsing and sensitive with the room temperature air, and I collapse next to her. She reached for a towel and placed it under her. She leaned over and kissed me, then got into a squat position and showed me the aftermath dripping out of her asshole. “See what you did to me? Is that what you wanted to see?”. I damn near passed out seeing my cum drip out of her. Her sheets are soaked with her juices and my cum at this point, but we didn’t care. As we cuddled, I knew I wanted more that night. We ended up having sex 2 more times that night and morning.

We hooked up a couple more times after that night, but she ultimately moved across the country for a job after graduation a month later. She told me a few weeks after that she was planning on fucking me that night and only took the shower to “get herself ready” for me. Our classmates kind of had a sneaking suspicion about us, but we never said anything. I will never forget that night.

Source: reddit.com/r/gonewildstories/comments/9mwmmr/wine_yoga_and_my_first_anal_experience_mf