Jessa and I started going fairly steady after that trip; it wasn’t common knowledge in the hiking club, but certain people did figure it out (including Sam, a junior in the club who had had a relationship with Jessa the previous semester). It didn’t bother us too much, because we had never actually discussed our ‘relationship status’ and were very much in a physical relationship.
She never came over to my place – an apartment shared with a senior couple and their dog. I transferred into school that spring, and just found an empty room to stay in. I spent probably two to three nights a week at Jessa’s for the remaining few weeks of school; that included weekend nights, when we’d fuck on a fairly regular basis. I actually don’t remember my first time having sex, but I do remember some pretty awesome times with Jessa.
My favorite sexual story with Jessa is from that May, during and after a party she and her roommates had at their apartment on the other side of campus. I showed up a bit early to help set up; a lot of our friends in the hiking club were there and as one of the newest members, I wanted to make a good impact on them all. Jessa, her three roommates and a few of their friends, and I started setting up. I made a few runs on my bike to the corner store to finish stocking up on juices and sodas for mixers, and snacks. Since I wasn’t 21 yet and didn’t want to use my fake ID (well, it was real, but belonged to my cousin: he and I were nearly identical), Jessa went to the liquor store for the vodka, whiskey, and beer. Not too many people were expected, but we all still liked to have a good, drunken time. I was still smoking more than drinking, so I usually limited myself to at most a nice six-pack, alongside my weed.
We finished getting everything ready about half-an-hour before the official start of the party, and we knew that some of our friends liked to come early for dinner; one of the other guys in the trail club was bringing pizza, but he wasn’t scheduled to show for another fifteen or twenty minutes. Jessa’s roommates and their friends escaped to their rooms with their shares of the booze – none of them were in the club, and rarely felt welcomed at our parties, even though we encouraged them to come out and hang with us. I suppose college is a time to discover your limits of exclusivity, and this was theirs.
With everyone dispersed, Jessa and I started making out in the main room. Her hands were on my biceps, and mine went to her hips. After some soft tongue-play, she grabbed my hand and pulled me to her room. She locked the door behind us and pushed me against the wall, kissing my face and neck. Her hands rubbed my chest and combed through my hair; I stroked her long blonde hair, smiling with pleasure. I ducked my head to catch her lips for a kiss; as I grabbed her ass to pull her up closer to me, she grabbed my hair.
Jessa bit my lower lip and growled, “Let’s have some fun, yea?”
She stepped back and quickly lifted off her blouse, exposing her large D-cup breasts captured in a lacy pink bra.
I bent forwards and bit, licked, and blew on her boobs, massaging them and stroking her body, from her belly to her hair. I kissed all over her chest, making her breathe heavily. My cock grew slowly, and Jessa moaned softly to my ministrations.
She finally pushed me back up to the wall, and got down on her knees. Jessa, as I learned throughout our short albeit busy sexual relationship, loved giving blowjobs. I placed my hands on her head, gently rubbing the top of her ears and smoothing her hair. She looked up at me and smiled, fumbling with my belt buckle and tearing my pants down to my ankles. My dick sprung forward in my boxers, bouncing. She grasped the shaft and stroked the silky polyester of my boxers back and forth, up and down my cock. My head peaked through the hole in my boxers, and Jessa leaned forward to lick the tip. I breathed a gasp of pleasure, a sigh of relief.
Still rubbing the fabric over my shaft, Jessa took the head of my penis in her mouth and flicked her tongue over the tip. I took handfuls of her hair in each hand, not controlling her movements as much as just binding us closer together. She slowly progressed along my dick, until all of it was inside her mouth. Jessa moved her hands to my waistline and briefly exposed my cock to the air as she pulled my boxers down. I stepped out of my pants and boxers, and took a wider stance as I now used my handfuls of hair to push her head back to my crotch. She reached behind me and grabbed my ass, pulling me towards her. I thrust my hips forward and pulled her head to me; she went willingly, of course, but kept her mouth and lips tight. When I was finally all the way inside her mouth, we both relaxed our grips and she moved a hand back to my shaft, stroking as she used her mouth to pleasure me.
I leaned back against the wall, lifted my face and smiled with my eyes closed. I couldn’t enjoy this blowjob like that for too long, and quickly looked back down at the bobbing blonde head, hiding and exposing my shaved genitals as she moved back and forth on my cock. Her hand slid down from my shaft to my balls. I squatted a bit, to let her play more below my cock, and her long, soft fingers took the invitation to massage my balls and rub the soft bit of skin between my cock and my ass. While she liked some assplay on herself, she didn’t like the idea of playing with my or anyone else’s asshole, so it was fine with me when she stopped her fingers short of touching my own tight eye. Jessa’s tongue and lips continued to wet and slick my cock as she went from one extreme to the other, from my head at the back of her throat to just inside her tightly pressed lips.
I couldn’t do anything but just watch and rub her head. I was glad to be leaning against the wall, because as I felt that friendly warmth start, it started in my knees and worked up. If I were just standing in the middle of the room, I would’ve fallen over. I grabbed the sides of her face and guided her back and forth, slowing her pace to help postpone my ejaculation. Jessa moaned disapproval – the vibration echoed around her mouth and resonated down my shaft. As she did in the car our very first time and for every blowjob since, she grasped my ball sack and massaged firmly, pulling and squeezing almost to a painful point – but this wasn’t painful. Her hand on my ass hadn’t moved this entire time, and now squeezed tighter and pulled me farther into her mouth. I put my hands on the back of her head and, breaking free of her own control, started to fuck her mouth.
She put both hands on my crotch: one still on my balls and one stroking my shaft, trying to slow me down. I wouldn’t have her back in control for now, and continued to abuse her mouth and throat, leaning back against the wall and using my hips and thighs to drive me harder and harder into her mouth. I felt the final surge starting again, and pulled her as far as I could onto me, leaning forward at the waist and pressing my butt against the wall. I exploded into her, holding her head to me until every drop had escaped.
I relaxed and released her head. She recovered from my abuse quickly and let my deflating cock out her mouth with a tight ‘pop.’ She kissed her way up my body and I stroked her hair and back, smiling at her as she ascended.
She reached my head and invaded my own mouth her tongue, biting my lips and pulling on my hair. She liked rough play, and if I had another word for ‘abuse,’ I’d use it. When we finally separated, she kissed my nose and grabbed my balls again.
“Randall will be here soon, babe,” she said as she turned around to find her shirt.
I grabbed at her hips as she bent down to pick it up; I pulled her ass to my naked cock and sent both hands to her pussy, covered with her jeans. She straightened up and leaned back into me, letting me rub her slit through her pants for a few second before turning her head and saying, breathily, “Not now, Jason. We’ve got the party.”
I pouted and squeezed her closer to me, “But you worked on me; it’s my turn!”
“Hah, later. Put your fucking pants on.”
I let her go and slapped her ass. I pulled on my boxers and pants, and we both spent some time in her bathroom cleaning up before going out to the main room to find Randall with a few other friends eating pizza and drinking beer. Randall looked knowingly at me and winked, “What’s going on, man?”
I shook his hand and replied, “Hah, you know. Nothing too much.”
“Horse-shit. Grab a piece before it’s gone, bro.”
Jessa and I each got a few pieces and the party started. For us, it had started a little while earlier.
It was a fun party, but started wrapping up earlier than usual. Finally, after most of the other guests left, there were only a couple of us still in her place and we went to Jessa’s room. Most of the people were drinking, and I packed a few bowls for the group to pass around.
Source: reddit.com/r/sexystories/comments/4xecn9/getting_started_mf_oral
Part 1: [The First First](https://www.reddit.com/r/sexystories/comments/4wz89u/the_first_first_mf_oral/)