[MT] First time anal with my college girlfriend. :)

My last post was a bit too kinky for some of you, so I thought I’d do something a little more vanilla – one of the earlier times we tried anal.

So my college girlfriend was a transwoman, and you can read more about her in my previous posts – she was gorgeous, with small supple breasts, big doe eyes, and an average sized, slim cock (5 inches long, ~4 inches circumference). In my first gonewildstories post, I described our first sexual encounter, and in the second, a kinkier cum-saving adventure. What I’m about to describe happened somewhere in the middle.

So after our third or so 69-cum swap adventure, we were laying in bed, cuddling, and Meg asked if I had ever considered anal. I told her my experience was pretty light – I’d tried sliding a finger or two inside myself a few times in the shower, but nothing really routine or anything. She responded, “Oh! Wow. How did you like it?” And I very quickly realized at that moment that what she really wanted was for me to top her, not for her to top me. I told her I’d liked it, but I didn’t really have the flexibility to do it comfortably with my hands. She giggled and told me she’d actually never done anything anal before, and hadn’t even considered topping a man. I think at this point I looked pretty embarrassed, but she was encouraging about it.

So we decided to mess around a bit the next night. I wasn’t sure who would top who, or how it would work. We were both too awkward to say anything explicitly, but we knew we both wanted to try something. We decided to prepare separately by giving ourselves enemas. We met up and went to Duane Reade together and bought some lube, which was one of the most awkward situations I’d ever been in. It’s bad enough buying lube at a drugstore, but both of us were so turned on by the idea and were semi-hard almost the entire time. It was fine for me – I was pretty good at hiding it in my waistband, but Meg, at my suggestion, had worn this really cute skirt I’d liked, and her cock was constantly coming untucked. It was late-ish at night so no one really noticed, but the drugstore cashier definitely did, and gave us a really awkward, skeevy “you guys are going to have some fun tonight, huh?” Anyways, we got out of there and went back to her dorm room.

As soon as we got in, she looked at me with the most sultry look and her tongue forced its way into my mouth. And she was so turned on. We’d been talking about life after school on the walk back to our dorm room, and I’d gone completely flaccid at this point, but clearly she hadn’t been paying attention to the conversation whatsoever. Meg was wearing this cute white skirt, with an oversized sweater. She pushed her body against mine, and I immediately felt her cock push hard against my inner thigh. I stripped off my shirt, and pulled off her sweater. She was wearing this amazing soft cotton bra underneath that perfectly contoured her breasts. I could see her nipples straight through it, and I quickly got hard. I picked her up and carried her to the bed. She kissed me all the while, and I could feel her hard cock against my belly as I held her. I tossed her onto the bed, and I began to kiss her neck. She moaned heavily, and kept pushing down on her cock with her hands. I pulled off her bra, nibbled on her tits, and, as I had often done before, dragged my tongue along the length of her cock. She shuddered, and I greedily took the whole thing in my mouth. I’d gotten pretty good at blowing her at this point. I knew I could make her cum fast by engulfing her in my mouth and moving my tongue back and forth on the underside of her cock. But she grabbed my head and whispered breathily, “Lick me lower.” I knew her ass was clean at this point, so I slowly dragged my tongue down her shaft, over her balls, and started to rim her. I held her cock in my hand and stroked her at the same time. She moaned and thrusted hard, and she tasted so amazingly sweet. And all of a sudden, she scooted up on her back, pushed me down, and we were in the 69 position again. But this time, after a little bit of a suck, she started to rim me back. I was a bit hesitant at first, but feeling her tongue in my ass was so sensual, so intimate.

So, this was actually a pretty difficult position to do anything in, so after about thirty seconds, Meg just gasped out, “Just fuck me.” This was it. My cock hardened at the idea, and breathing heavily, I pushed her down onto her back, turned around, grabbed the lube, and lathered her ass and her whole body. I laid my chest onto hers, and we kissed and slid around over each other. And slowly, my cock found her ass. I slowly slid in, and Meg moaned heavily. After a few minutes of careful, slow play and stretching, she told me to go deeper. I complied, and pushed against her prostate. She moaned heavily. I was worried her ass would be sensitive to too much movement, so I stayed deep inside, and mostly just moved around within. She moaned heavily, and after a few more minutes of this, her cock was covered in pre-cum, something I’d never seen before. It was glistening. I scooped some into my fingers and licked it, and it tasted so deliciously sweet. She stared at me lustfully, and I stuck my fingers into her mouth, and she let out a gasp. I started to fuck her a little faster, staying mostly inside her, pushing against her prostate. And immediately, after a few more seconds, her cock started to dribble cum, and Meg let out this shudder. But still, she stayed hard. More and more I fucked her, and bits of cum dribbled out. Eventually, I couldn’t take it anymore, and I pulled out of her, and licked the cum off her cock. “What are you doing?” she asked, “I’m not done.” This was pretty foreign to me and apparently her cumming at this point wasn’t really a sign of her finishing.

Before I could say anything (my mouth was still full of her cum at this point), she pushed me down, and her cock found my ass. She kissed me, stealing some of her cum back, looked at me with the most sultry eyes, and dribbled it onto her cock and my ass. Then she slid in. Her cock was slim, but it still felt enormous to my virgin ass. I gasped, and she brought her body back onto mine, and I bathed in the feeling of her tits against mine, her cum all over us, her cock pushing against my ass. Then she started to fuck me. It was a bit sensitive at first, but my cock was so hard I was ready and willing. Her small tits bounced as she thrust into me, and her hair swayed, tickling me all over. She was shorter than me, so she leaned down as she was fucking me and started to suck on my nipples, which I admit are just strangely sensitive. And I was ready to burst. She told me, “Let’s cum at the same time.” I nodded, and she grabbed my cock in her hand as she started sucking my nipples again. She pushed her cock back into my ass, against my prostate, and began to moan, thrusting faster and faster. Within seconds, I gasped, “I’m going to cum,” and she let go of my cock and started to fuck me faster and faster. I felt a rising tension in my ass, and she said, “Me too.” And within seconds, she pushed hard into me, and I felt her cum a huge load. I could just feel tons of pressure down there, and her cock started moving in and out more smoothly. And almost immediately afterwards, I shuddered and came all over her chest. It was the most intense orgasm, and some of my cum even spurted up to her face. We collapsed in a heap on each other, and kissed, covered in our juices.

Hopefully that one was a bit more vanilla for you guys. I’m running out of stories to tell, but I definitely still have a couple more left. :) Let me know what you think!

Source: reddit.com/r/gonewildstories/comments/6wd7ow/mt_first_time_anal_with_my_college_girlfriend