The college years with Jess and Tommy shattered pretty much every one of my original ideas about sex. The girl that grew up with super conservative parents learned to embrace every fantasy. I learned that withholding desires because someone tells you they are wrong is stupid, and harmful to your mental health.
Jess, Tommy and I had been having oral sex, or masturbation every day, some days multiple times, since our first encounter in the co-ed showers. I finally had my fix of sucking cock, and while I did have to share the tap with Jess, she knew that I was much more into swallowing cum than she was. Tommy was just happy to have two hot chicks desperate for his cock. (Not that Tommy would ever refer to us as ‘chicks’)
It was a typical Friday night in November. We had all completed everything we had to do for the week, thanks to Tommy nagging us relentlessly. Jess had managed to smuggle a small bottle of vodka into our room, along with some coke as a mixer, to replace the horrible wine coolers we had been drinking. Tommy ordered a Pizza for us. And of course Jess went on the hunt for some porn to borrow, returning the movies we she had borrowed the previous week.
It hadn’t occurred to me yet that Jess had a definite preference for the type of porn that she liked best… until that night.
We started off the night like we did almost every night, sitting around and chatting. Jess and I sitting on our beds, Tommy would sit on one of our beds with us, or in a chair in between us, depending on if one of us girls was feeling particularly possessive that night or not. This night he was siting on a chair in the middle.
Our dorm room was at the start of the heating ducts for the wing that we were on, which meant in the winter our room was always hot. This combined with the idea that neither one of us really cared about being naked around each other, or Tommy, meant that we never wore anything more than a t-shirt and panties in the room, and some times less. That night was nothing different, Jess had a crop top on, and some panties that were little more than dental floss. I just had a long t-shirt that almost covered my ass, and that was it.
Tommy was talking wish me about computer science, and some pointers on computer code that I was still trying to grasp. Jess was a bit bored, and started looking through the small stack of Porn movies that she had obtained. Finally deciding which one to watch, she posed it in. Tommy and I continued to chat for a couple of minutes while the deep moans came from the TV.
Jess has this Horny look that she gets, when the world fades away and the only though in her mind is on sex. I love that look on her. Anyway she had that look on her face. Her breathing was shallow, her nipples were poking through the front of her t-shirt. I looked at Tommy and smiled, then glanced towards her. I was vaguely aware of the scene changing on the movie, when I heard Jess whimper. On a scale of one to ten, that was horny level fifteen for Jess.
Tommy and I broke the conversation off and looked over. Jess was leaning back, her hand between her legs. On the tv, this girl was having a cock slowly pushed into her ass. Every thrust got another whimper out of Jess. By the time the girl on the movie was having her ass pointed, Jess’s eyes were rolling back in her head.
I smiled at Tommy and got up, walking over to Jess’s bed and tossing my t-shirt to the side. Jess moved to the side of the bed, knowing that I wanted to eat her pussy out to get things started. Look I love cock, but I am a total oral addict, and when it comes to giving oral I want pussy as well as cock. The more the better. I went to work between Jess’s legs licking her dripping wet pussy and licking and sucking her clit. Jess gets very wet, but this was unusual for her.
“Fuck I need that…” she whimpered as my lips coaxed an orgasm out of her. The scene on the film ended with the girl getting cum slashed over her tits, as close to the same minute Jess grabbed my face and crushed my mouth against her clit, her body convulsing in an orgasm. Jess collapsed on the bed gasping for air, taking a few minutes to recover.
I walked back to my bed, sitting back feeling quite proud of myself. Tommy was already stripped off and coming towards me ready to eat me out, though soft his massive ensest hikayeler cock was already swelling and I was looking forward to wrapping my lips around it. A smile spread across my face as I spread my legs wide, bringing my knees as high up as I could. Tommy knelt down in front of me, using his hand to spread my lips wide. My pussy opened for him, wet and ready for his tongue. The tip of his tongue flicked across my asshole first, then ran up my slit all the way to my clit. It felt so good, I sighed with pleasure. Again and again he went back, starting at my asshole, and moving to my clit; it was magic.
I saw Jess get up and walk across the room. “Let me have her.” She said to Tommy. Tommy backed off, letting Jess take over licking and sucking my clit. Jess was on her hands and knees, legs spread, ass in the air. “Fuck me…” she begged Tommy as she went back to work on my pussy. The pleasure on both their faces was clear as he filled her pussy, Jess sucked my clit hard, making a slight moaning that vibrated through my whole pussy.
Tommy slowly started fucking Jess. His stroked matching in time perfectly with her licks. I could tell that both Jess and Tommy were enjoying themselves, which only heightened my enjoyment.After a few strokes, Tommy was starting to pick up the pace, and I could hear him slapping into Jess with each stroke.
“My ass!” Jess Gasped. “Fuck my ass.”
Tommy looked shocked, and missed a stroke. Tommy had never had anal sex before, but he certainly wasn’t going to disappoint Jess. He pulled out of her pussy, and repositioned himself. I was there, looking down at Jesse’s face. She tried to lick my pussy, but she completely lost it. Her face reflected ever sensation her body was feeling. As Tommy slowly pushed his cock into her ass, here eyes rolled back; her face was a mask of total bliss. Tommy thrusted a few times, trying get her ass to stretch around his girth, and every motion was reflected on Jess’s face. Jess’s eyes focused on mine, a heavenly smile spread across her face. It was almost as If I could feel her pleasure with the glaze she locked with me.
For me Orgasms are about seventy five percent mental. And the site of Jess’s body being over taken with pleasure pushed me over the top. Jess and I ended up in an orgasmic mess, both cumming around the same time. I recovered quickly, but Jess with her ass bing pounded from behind just kept cumming and cumming like the energizer bunny.
Tommy was fucking Jess like a porn star… but eventually his strokes faltered. His grip on her hips tightened. “Oh god.. I’m going to cum…” He managed to gasp. In one motion Jess pulled off his cock, and spun round, grabbing his cock and drained every drop of his cum down her throat. Now this was the early 90’s so while the idea of Ass to Mouth is common place these days, back then it was a shock to me.
We spent the rest of the night recovering before heading to the Co-Ed showers to clean up together, and parting ways with Tommy. It’s funny, we were together pretty much every day, but he never shared either one of our beds for the night.
Sunday morning Jess and I were having coffee at the local Doughnut Shop as usual, and as usual the conversation eventually turned to sex. I started asking her about having Tommy fuck her ass and what is was like.
Jess admitted that while she enjoyed having her pussy played with, and licked, when it came to fucking she preferred anal sex. It stemmed from the first guy that she had sex with. At the time she was too embarrassed to go to the family doctor for birth control pills. So rather than risk pregnancy they just always had anal sex. Obviously these days she had birth control, and had vaginal sex, but for her it never had nearly that same level of enjoyment as having a guy in her ass.
I asked her a hundred questions it seemed. I was intrigued. And while the idea of real people having anal sex had never occurred to me before that Friday, I had to admit that my thighs were a bit wet just thinking about the idea. I asked her about sucking him off at the end. Jess explained that she always ‘cleaned’ before sex to make sure if she did get lucky, there wasn’t any chance of it being ‘dirty.’ “Besides, at that point in time, when you are horny as fuck, you probable would’t notice anyway.” Jess could obviously read my mind at that point. When we started to leave she grabbed my hand and started walking towards the school garage.
Jess took me to this video store on the other side of town. The place always looked tiny from the outside with a pitiful selection of movies. However the secret was that the “back room” was actually four times the size of the front. In this case the back room was a selection of porn movies, slutty lingerie and sex toys. Jess went to the selection of Dildos and started looking at them, gauging their width with her fingers. After mulling over the selection she selected one that was this fairly ugly hard purple plastic resembled a cock shape in the same way that a Monet painting resembles a person. Jess held it up and smiled, “Here you need this! And…” She grabbed some lube, “This as well.” Finally she looked around and grabbed a small purse vibrator and added it to the collection. The blank look on my face told Jess I didn’t have a clue. Jess leaned closer whispering into my ear, “You want Tommy to fuck your ass don’t you?”
“Ummm I”
Jess laughed “Of course you do you little slut!”
I cracked a smile between Jess and I ‘slut’ was a term of endearment. “I’m just… worried I guess.”
“Look you were scared shitless about getting waxed right?”
My smile widened. I had indeed been worried… over nothing. And at this point I can’t ever imagine not being waxed. “So… we are going to get that ass of yours ready to be fucked.” Jess grabbed the selection from me and went to the counter where a forty something year old woman rang up our packages. I remember thinking at the time that she was too “Old” to be working in a dirty store like this… not in my fifties I realize how ridiculous that thought was.
I spent the week playing with my new toys. My first toys. Jess unleashed a monster that day, I have easily spent thousands on sex toys over the years since then. Our nightly masturbation sessions included me working up to taking the ugly dildo in my ass, while using the vibrator on my clit. Jess helped me understand the right amount of lube, positioning etc.
It’s sad, I have read so many stories of women that either never try anal sex, or have such a bad experience the first time that they swear off it for ever. One of my girl friends admitted that her husband once pulled out during sex and shoved his cock into her virgin ass as a surprise. It amazes her that I could not only find anal pleasurable but actually orgasm from it! I am so glad that my first experience was as amazing as it is, I couldn’t imagine NOT having anal sex in my life!
Anyway Friday night came around again. Jess sent me off to the bathroom an hour early with the “tools of the trade” to make sure I was nice and clean and ready for action. Tommy arrived as usual with food, that night was Chinese food. We ate and chatted as normal, building up to the hot sex that always followed. We were part way into the porn movie we were watching that night. Really the movie didn’t even register for me because my mind was so preoccupied with both excitement and apprehension.
Tommy was lying back on my bed, like some unholy sacrifice to two horny succubi. His cock was rock hard and he was ready. I crawled across the floor, eyes on my target. My mouth watered; I could feel a trickle of my own wetness running down my thigh. The idea of what I was about to do had me even hornier than normal. Tommy looked down as I rose up between his legs, wrapped my hand around his cock. An evil smile spread slowly across my lips.
Suddenly the enormity of what I was about to do struck me. My fingers couldn’t quite wrap fully around Tommy’s girth. Was he bigger than night than usual? My stomach fluttered, suddenly I wasn’t sure if I could do this. Tommy was MUCH bigger than my practice Dildo; I can’t quite get my fingers all the way around his cock shaft when it’s fully hard, and the head is even a bit bigger. I took a deep breath, the desire inside me took over again, I spread my lips. I licked the trickle of precum running down his smooth shaft, and then took the tip of his cock in my mouth. Tommy’s head fell back on the bed, a satisfied “Oh yeh…” Escaped from him. Then I felt Jess spreading cold lube on my asshole. One of her fingers slipped in my hole, and any doubts I had were forever vanquished.
I climbed on top of Tommy, straddling his cock, I took some lube and coated the entire shaft. Tommy looked at me with a confused look; we had never needed lube for fucking before. Then he watched as I angled his cock back further. As the tip of his cock touched my asshole, I clenched unconsciously, then tried to force myself to relax. I lowered myself onto the tip of his cock, and felt my muscles resist. At first it was only part of his head that slid into me; about the same as my practice dildo. Another deep breath and I tried to relax, the wide part of his head sliding in slightly, I could feel my hole stretching. I closed my eyes, focusing on my ass, willing myself to open for him. Deep breath, letting it out and sliding down a bit more. Deep breath, relax, then I felt Jess’s mouth on my pussy.
Jess licking my clit made all the difference. Another deep breath, letting out a moan, and I finally felt the head of Tommy’s cock fully into my ass. Jess gave me a wicked grin as she stopped licking my pussy and moved to straddle Tommy’s face. If we were two succubi, Tommy was our horny angel that night. It seemed like it took forever for my body to finally take Tommy’s full length. Once the head was in, it was an agonizingly slow journey to the bottom. With every inch I felt myself open more and more, both physically and mentally. I pictured Jess the week before, that look of total bliss as she was filled, and I knew. I wish I could adequately describe the feeling of having my lovers cock fully in my ass for the first time. It was like a wave of warmth spreading through my entire body waves of absolute pleasure engulfing me. I felt open, and full, and so emotional I wanted to cry… and horny as fuck all at the same time.
Jess slowly ground her pussy into his mouth. I started matching her grinding, each movement agonizingly slow sliding Tommy’s cock out slightly and then pushing it back into my tight hole. Jess’s eyes took on that far off look she gets when she Is about to cum and I felt that same feeling build inside of me.
It was amazing. I had the entirety of that massive cock in my ass. It felt so good, I didn’t want to move. Jess’s eyes rolled back and she gasped and whimpered her way to her first orgasm. I felt Tommy’s hips move under me, slightly rocking, moving inside. God it felt so good. Part of me wanted to have him fucking me hard like he had done to Jess the week before, but I knew I wasn’t ready for that yet. Jess grabbed the small vibrator, turned it on and handed it to me.
After a few moments of recovery, Jess once again started grinding her pussy on Tommy’s mouth, I leaned back slightly, butting the vibrator on my clit, and slowly started rocking back and forth once again. Tommy let out as much of a stifled moan as he could considering is mouth was occupied, and his tongue was licking Jess’s insides.
It was like a whole body sexual feast. My ass was filled, and the rocking motion was hitting all the right spots. My clit was buzzing both from the vibrator and from the way Tommy’s cock was position inside of me. My eyes were feasting on Jess’s gorgeous body. Her face was getting that look again, a glimpse of heaven as her second, and much bigger orgasm approached.
“Oh fuck” I gasped. Dropping the vibrator. My own orgasm had snuck up and over took mine. I leaned forward, grabbing Jess’s hand. I rocked forward pulling Tommy out of my ass about a quarter of the way; Jess and I locked eyes. I thrusted my hips back as hard as I could. The sudden thrust pushed me past that point of no return, and both Jess and I exploded into orgasms so intense that it left me in tears.
At some point my mind cleared enough to become aware that Tommy was rocking in and out of me. Still breathless, tears running down my face, but aware of my surrounding to some extent, I lifted myself up slightly, giving Tommy more room to move. The thrusts were deeper and harder, and I have to admit getting a little uncomfortable. Then I felt Tommy’s cock swell as he approached his own orgasm. His cock was all I could take normally, but the swelling felt like it was going to split me in two. Just like Jess had said, without a second thought I pulled off of him, and slid down his body. His balls tightened as I grabbed his cock, and a gorgeous fountain of cum exploded into my lips as I stroked every last drop of the heavenly fluid from him.