Avery’s Freshman Year Part 2: Taking Tom’s Virginity, female author [MF]

Part 2 of a series of stories from my freshman year at a small college in New England. As always, I’m open to critiques and feedback on my writing, I just ask that you please be respectful in the DMs.

This is a bit later in the fall semester than Part 1, right at Thanksgiving. As I noted before, this series will jump around a little chronologically, based on what I feel like writing about. Without further ado, how I took Tom’s virginity. ♡Avery

As you guys learned in Part 1, my best friends in college were Chris, Tyler and Tom. Chris and Tom were roommates, and Tyler and I lived down the hall a few rooms, Tyler with the marathon hike of like 10 doors down (which he never stopped reminding us about).

After the infamous “Cover Avery in Cum” incident in Part 1, things had settled back down into a pretty even rhythm, lots of game nights, lots of fun. Like I said, we had lowered inhibitions, but college isn’t a 24/7 porn set. The only real change was my Instagram had 3 new likes on every picture that I was wearing anything remotely resembling a bikini, short shorts, or any outfit that might denote that I wasn’t a shapeless blob. Thanks for the free likes guys, I know you love my beach pics lol.

Anyway, Tyler and Chris had decided to go on this backpacking trip with their church’s college outreach program (super cool actually 10/10 would recommend). My roommate was yet again out at her boyfriend’s off campus apartment for the weekend (tbh, i think she only ever slept here during the week) which left Tom and I to fend for ourselves for the weekend. Which is why we found ourselves in him and Chris’s room playing FIFA on a Friday night like a bunch of bums.

As the night progressed, Tom seemed like he was building up to a question. He was asking how I felt about what we did that 1 night (it was hot ngl), had I ever done something like that before (no that’s a first), and if I had been with anyone since moving on campus this year (2 guys yes, probably gonna get to those later). Eventually I was like, “Tom, what’s up man, is someone a little jealous” slightly nudging him and giving him a wink.

He told me since coming to college, he had met a few girls he liked (me included apparently), but he was super nervous to make a move since he had only ever made out with a girlfriend I’m highschool, and I was the first girl he’d ever seen I’m a bra and panties (a sports bra and athletic thong at that). I was like, “well why don’t you just do something about it then?” It seemed obvious to me, maybe not to him, but I had let him and 2 other guys cum on me, that may be a hint that I wouldn’t be completely disinclined to a hookup. I explained that to him and he seemed pretty dumbstruck. After the shock of “omg a girl would sleep with me” wore off, I explained that while yes, I was a girl with needs who wants to get laid, 1. We were not gonna be a couple, I like our friendship and the group we have. 2. Tyler and Chris can never hear about it, again, going back to #1.

He bumbled out a response about omg he would never tell and I would be the best person ever if I was serious about this. He asked how we would even going about doing this and I laughed and started “now you see Tom, when a man loves a woman very very much…” before catching a playful shove, and I told him seriously, if he wanted to do this, to come down to my room in a few minutes, because I was not having sex in the Tom and Chris man-funk room. He blushed and said something about he needed to take my earlier manscaping advice that he had yet to act on but then he would come down. I gave him a chaste kiss on the cheek and squeezed the front of his shorts as I left to head back to my room.

I decided that I didn’t want to make this more than it was, so I didn’t go overboard with lingerie or anything, but I did decide to put on a pale blue bra and thong set underneath my run of the mill Nike shorts and a baggy tshirt getup. BTW, if a girl matches like that, we planned for you to see it, just be appreciative.

Maybe 15 minutes later, a knock at my door let me know that Tom was there and I let him in. He awkwardly stood by my bed and asked me what to do next. I stepped close to him and took his hands in mine. I guided one to my small, B Cup breast, and the other to my fairly toned butt, barely covered by my shorts. Before wrapping my arms around him into a deep, passionate kiss. We kissed again and he started to move his hands around, ever so slightly and more boldly, as I encouraged him with soft moans in his ear when he touched or squeezed a sensitive spot.

I pulled away and asked if he wanted to see a girl in her underwear again and he just sort of nodded. I slipped my tshirt over my head and pulled my shorts quickly to the floor, before spinning around in front of him, giving him a look at my boobs in a decent pushup and a small thong that barely covered the essentials. I stepped back into his arms before pulling his own shirt over his head, when I got to take a chance to admire his well built, if not super defined chest and arms. He carried a little extra in the tummy, but I blamed that on my snacks at game night more than anything. Overall, he was fairly attractive, and in that moment he had my full attention.

I eased Tom back onto my small dorm bed and climbed on top of him, continuing our makeout session as his hands found my butt and I leaned over, giving him a tantalizing view down my bra. He struggled to take it off for a minute, before I took over and tossed it to the side. I could feel his growing excitement between my legs as I grinded myself alone his length while dangling my small breasts in his face, which he graciously reached up and softly kissed and ran his tongue around my small, hardening, dark-brown nipples.

At some point I decided to take it further, kissing my way down his chest as he softly moaned when I hit the sensitive area along his sides. I slipped off his shorts, releasing his now fully hardened manhood, which was maybe 5-6 inches, and decently thick (perfect in my opinion, gets the job down well without any pain or discomfort later, sorry not sorry to every guy with “my massive 9 inch horse cock”). He had trimmed things up which I appreciated, since I was currently sporting like 3 day old stubble from the last time I shaved myself down there. I teasingly licked my way down his shaft before taking him in my mouth,bobbing up and down a few times before standing up, not wanting things to end too early.

I slipped off my thong, bending over to give him a good view of my vagina and butt, before reaching into my nightstand for a condom and some lube. I was definitely turned on, but lube with condoms never ever hurts. I climbed back on top of Tom as he looked up at me kinda awestruck. He whispered that I was absolutely beautiful. I blushed and opened the condom, slipping it on for him before squirting some lube on the end of my fingers, which I graciously rubbed between my legs, giving him a little self-love show in the process as I prepped my body to take him inside me.

I asked him if he was absolutely sure he wanted to do this with me, and he nodded yes before reaching up to kiss me again. I reached between my legs and positioned him at my entrance, sitting up and easing my way onto his rock hard shaft a little bit at a time. For a few strokes, I placed my hand on his chest and bounced my way further and further down his cock until I bottomed out, with the lips of my vagina pressing down against his pubic bone.

Keeping him this deep inside me, I rocked my clit against him, moaning in pleasure at the teasing friction. I leaned forward to kiss him and his hands grasped onto my buttcheeks, stretching me open and allowing him to push as far into me as possible as he built a steady rhythm, thrusting into me as I softly moaned his name in his ear.

After a few minutes, I could feel him start to swell as he picked up speed, obvious on the edge of his first orgasm in a woman. I moaned for him to cum for me and that was it. With a few powerful thrusts as he reached his orgasm, deep inside me, as I kissed his neck and held him tight. I felt him slip out of he as I got up, and asked if he’d like for me to help him clean up. We took a warm shower together, and I let him watch me find my own orgasm under the water, rubbing my clit and moaning his name as I rested my head against his chest for balance.

I let him spend the night cuddled against me, both of us still naked. We didn’t go for another round or anything, but this isn’t the last appearance of Mr Tom, I promise.

Thank you for reading this far and sticking with me! If this is something you enjoyed, or you have criticism or feedback, drop me a comment or I’ll see you in my DMs!

♡Avery

Source: reddit.com/r/gonewildstories/comments/pjh63e/averys_freshman_year_part_2_taking_toms_virginity