“Well,” I replied, taking a deep breath. “This was my wildest night.”
As you know, I dated a girl through most of college. We met and hit it off as freshmen, and saw each other on and off through the rest of school. I would be lying if I said that I was faithful to her. I was an immature jerk, like most guys that age and had a couple of girls on the side who made themselves available for a little fun.
So, as was often the case, I was at my girlfriend’s apartment late in the evening watching TV and cuddling on the couch. Melinda was average height, average build, but had nice legs, and a cute face with short blonde hair and blue eyes. She was a marketing major and was a lot of fun to be around.
This particular evening was nothing out of the ordinary. We waited until her three roommates went to bed and began kissing heavily. My hand slid up under her sweatshirt to squeeze and tease her sensitive nipples, as she slid one hand down to rub my hardening shaft through my jeans. Our tongues teased other softly at first and then with more abandon as our hands continued their journeys over our young flesh.
I moaned lightly as she rubbed harder and faster against the denim material holding my swollen cock. I cupped and squeezed her breasts in return, and she breathed raggedly in my ear as she reached to unbutton my fly. We slipped her sweatshirt off as I slid my jeans and underwear down my legs to the foot of the couch. Pulling the obligatory blanket (roommate shield) up over my head, I slid down to suck and bite on her nipples. Holding my head, she guided my mouth from one nipple to the other, encouraging me with her breathing when I gave one the perfect nibble.
As I sucked, I slid one hand up to lightly rub her pussy through the material of the shorts she was wearing. The windshorts made their sexy, slippy sound as my fingers stroked gently over her mound. Pressing the heel of my hand against her clit, I could actually feel her swollen lips through the thin material with my fingers. She responded by pushing her hips up against my hand and pressing her clit hard against me.
“Oh baby,” she breathed in my ear. “That feels so fucking good. Your hand down there.”
Encouraged, I slid up to lay beside her on the couch and kissed her deeply. I maneuvered a couple of fingers around the crotch of her shorts and pulled back her moist panties from her now swollen pussy. Moaning deeply in my mouth, she slid her hand down my stomach to put a reverse grip on the cock now pressing against her thigh.
Teasing gently, I slid two fingers slowly up and down the wetness between her lips. Moving from the very bottom, I slid my fingers up to rub teasing circles around her clit and then back down. On every other circle or so, I would tease just the first digit of my finger into her tight pussy and then back out to tease her clit.
She pulled away from our kiss to look me deeply in the eyes. As my fingers played along her soaking wet cunt, she stared at me with the look of lust that only a 20 year old girl is capable of. A look of never having known sexual disappointment, and eager for the next discovery a lover has to offer her. I wanted to cum all over her right then and there. And as if sensing my discomfort, she stopped stroking up and down my hard shaft and gently teased her thumb across the head of my cock, rubbing the precum across the swollen head. During this whole time, though, she never looked away from my eyes and continued to fuck her hips up against my fingers, urging them farther and farther into her as my thumb played across her swollen clit.
“Chris, I’m so close to cumming right now, but I want you inside me when I do,” she whispered. “Please baby, will you fuck me now?”
Nodding, I stood up by the couch to slip my shirt over my head. In the same instant, she slid off her shorts and panties, and wrapped her outside leg around my thighs to pull me back onto the couch, positioning me between her legs. Sliding up, I placed the throbbing head of my cock between her lips, finding the opening to her tight pussy. Wrapping her thighs around my hips, she moaned and squeezed her nipples. As she watched under the blanket, I took my cock in my hand and slowly slid the head up and down her wet slash, vibrating it quickly on the top against her clit. She moaned and looked up again at me. God she was so hot! She bit her bottom lip and breathed in deeply, the sweat just starting to glisten on her forehead and cheeks.
“That’s it, baby,” she moaned. “Slide it in me. Slide it in now.”
Still wanting to tease her, I just pushed the head of my cock in and out of her several times. Loosening up the tight entrance, her juices coated me. I teased in and out until she was just starting to take a breath in and, then pushed my entire length deep into her cunt. Her eyes widened, and her breath sucked in sharply before a smile spread across her face. She squeezes her tits and closed her eyes as a slow exhale came out.
“Mmmmm,” she moaned. “That’s it. I love the feeling of you deep inside me. I love how you fill me up.”
Using her legs against my hips and ass, she began to guide me in and out of her. Controlling the speed as to what felt good to her, she showed me how she wanted to be fucked that night. I pushed my cock quickly in and out of her. Watching her face. Feeling her pussy squeeze me at the bottom of every thrust, and her lips glide on my cock as I pulled out. I could feel her juices on my balls as they slapped against her asshole each time I thrust all the way in. Fucking her hard, and then harder as she raised her hips to meet every thrust.
Looking up at me again, she breathed, “I want to cum now, baby. I want you to make me cum. Shoot deep inside me, and make me cum.”
I looked deep into her lust glazed eyes as I began to fuck her in earnest. Pummeling her pussy with my body. Fucking my entire length in, and out of her. on. ev. ry. thrust.
“Yesss,” she moaned. “Just like that. Just like that, Chris. Just like that. Make me cum, baby. Make me cum. Make me cummm. Make me cummmmmmm.”
As she spasmed around my cock, I pushed in as deeply as I could, shooting what felt like quarts of sperm deep into her young nubile body. I then began fucking again to carry her through her orgasm. Her body arched beneath me as I fucked her, her head thrown back against the pillow, trying to gasp as quietly as possible as she came all over us.
Collapsing on top of her, we drifted off to sleep for about an hour. Waking up, we got dressed and she showed me to the door. Kissing me gently, she watched from her door as I crossed the apartment complex to my own apartment, waving goodnight before slipping inside.
Inside my apartment was one of my roommates and a good friend of ours from our fraternity’s sister sorority. She had stayed over a little late to get some accounting homework done with Richard, but seemed genuinely glad to see me come in. We shot the shit for awhile before I laid down on the couch to do some reading of my own, while they finished up their studies in the dining room.
When they finished, Jen came into the living room and asked if it would be okay if she curled up in a chair to watch some TV for awhile as her roommate had a date over that night. Richard and I both said sure, and he headed off to bed for his 9:00 class. After some welcome chitchat, she convinced me I was through studying for the night.
It wasn’t hard to be convinced. Jen was about 5’7”, long blonde hair, gray eyes, tight ass and a huge pair of tits pushing against her sweater. We broke out some pillows, I changed into a t-shirt and sweat pants, and we curled up on the living room floor to watch TV.
After some initial nuzzling on my neck, and rubbing on my chest, my dick once again sprang to attention. Jen got up on one elbow, looked at me, and with the other hand, squeezed my cock through my pants.
“You know Richard is my big brother, and he would kill me if he saw us doing anything. But there’s no sense in letting a hard on like this go to waste, is there?” she asked innocently.
I certainly couldn’t think of a reason to let it go to waste, and so was more than receptive when she leaned down to kiss me. My hand slid up her side to find one of her breasts, which I squeezed appreciatively as our tongues darted in and out of each other’s mouths. Feeling her nipple harden against my searching fingers, I squeezed it gently. Jen responded by moaning into my mouth as we kissed.
Her hand moved from my cock to untie my sweatpants. She had them undone quickly, and slid her hand into them and under the waistband of my boxers. She wrapped her hand around my hard dick and began stroking it up and down. It was my turn to moan and I did so approvingly, as she squeezed and stroked my raging hard on.
Sitting up, she glanced nervously at Richard’s bedroom before looking back at me. I then saw her thoughts flash across her face as she quickly decided why the hell not. She then smiled at me and said, “Let’s try something.”
Jen quickly stripped off her sweater, revealing the perfect white tops of her breasts straining against her bra. Seeing me stare, she giggled and said, “I think you’re going to like this.” And with that, she unhooked her bra, letting her full firm breasts free. The pink nipples, thanks to my previous attention, poked straight out from Jen’s breasts, and she absentmindedly pulled on one of them as she told me to stand up.
As I got up from the floor, she stripped my bottom half totally nude. She then got to her knees in front of me, and put one hand on my hip and cupped the other sensuously on my ass cheek. She then slowly slid her mouth all the way down the entire length of my shaft, until her chin was resting against my balls. She then sucked deeply as she slowly pulled off my shaft and teased my swollen cock head with the tip of her tongue. She wrapped a hand around me and began stroking slowly back and forth as she said, “Yummy! You’ve already seen a little action tonight didn’t you? I can taste her on you. Mmmm, but now I need to get you nice and wet again.”
For the next ten minutes, I got a blow job to make a hooker blush. Jen was voracious; sucking me in and out of her mouth, grabbing my ass to pull me deeper inside and down her throat. She would grab my head with her hand and hand fuck me really fast while she buried her face in the juncture between my thigh and balls. Inhaling deeply she would look up into my eyes as her tongue darted across the bottom of my nut sack. I could only look down and moan and try to keep the big goofy grin from spreading across my face.
Once I had her spit dripping from my balls, she finally seemed satisfied and reclined back onto the floor resting her head on my pillow. Taking my hand she pulled me down and positioned me so that I was on all fours above her with my cock resting against her heaving chest. She then squeezed those luscious tits together and said, “I want you to fuck me.”
Sliding my hard wet dick between those warm pillowy breasts was heaven. I was already so turned on from the blow job I didn’t know how long I could last, but I was determined to try. I began slowly pushing in and out, rubbing the length of my shaft against Jen’s breast bone. On every third or fourth stroke she would lean her head forward and suck the head of my cock or tease it with her tongue. I began to fuck a little faster, feeling the beginnings of my second orgasm of the evening warming up inside me.
I took over holding her breasts together so I could gently squeeze and pinch her nipples while I ground against her chest. Moaning, she reached around and grabbed my ass with both hands, encouraging the faster rhythm I was fucking her tits with. She pulled me faster and faster against her chest, her mouth now at the juncture of her cleavage so I could move in and out of her teasing hole on every stroke.
Gasping, I told her I was close to cumming. She stopped me briefly, and told me she wanted me to cum on her face. She pulled me up and I got into almost a push up position spread eagled over Jen’s face with my cock buried deep in her mouth. While holding my position on my hands and toes, I thrust my cock quickly in and out of her waiting mouth. Her hands on my hips encouraged my rhythm and stroke depth.
When she reached down to pull on my balls as I continued to face fuck her, I finally could take it no more. I sat up and got on my knees above her face and jerked off another amazing load all over Jen’s waiting face, her mouth opening hungrily for my seed.
“Oh, my god!” I gasped, collapsing against the front of the couch.
“Mmmm Hmmm,” Jen purred contentedly, as she used a finger to clean my cum off her face and into her hungry mouth. “That was yummy!”
I walked to the kitchen to get a wet paper towel, and then helped Jen clean the last remnants of me off of her smiling face. She kissed me warmly after getting dressed and said, ”Thanks, Chris. That was so much fun. Maybe we can get together again some time.”
And we did. But that’s another story. And she was elected sweetheart of our fraternity the following year. And that’s another story, too. But Jen did know how to campaign without campaigning.
After she left, I read to the end of the chapter I had been working on earlier, and called the real “other woman” of that time. She was still up, as usual, and was eager for me to come over. I cleaned myself up this time before leaving. I slipped out of my apartment, somewhat nervous about the fact that my girlfriend’s door overlooked mine, but hey, she was probably already fast asleep. Besides, I had never gotten caught before, and that’s reason enough isn’t it?. I walked the block over to Devon’s house, and she let me quietly slip inside.
One thing about Devon’s roommates; they came in and out at all hours. So most of our extracurricular activity was confined to her bedroom. Not that that was always private either. The roommate that she shared the same room with never seemed to be bothered by my presence. Donna and I were oddly good friends outside of the bedroom situation, but she didn’t really want anything to do with me inside it. She seemed to be more than content just to listen or watch me pleasure her friend.
Devon quickly pulled me into her bed rubbing her body against mine. She had a thing about flannel pajamas, but she seemed to be able to pull it off. Besides the thought of her wet mound underneath that soft material was fantasy material for many years.
Anyway, it wasn’t long before we were both totally nude and stretched out on the bed. I had my head buried deep in Devon’s pussy and we were well on our way to her second orgasm of the evening, when Donna walked in.
“Hi, Chris,” she said as she walked to the closet to change clothes. It was obvious that she was more than a little tipsy when she patted my ass on the way by. I jumped but went back to work trying to help Devon over the top. My tongue licked hungrily in and out of her hole, as she fingered her clit to orgasm, thrusting noisily against my face.
“Mmmm,” she moaned as she settled back. “I looove the way you finger fuck me, Chris. And oh my god, you were driving me crazy tonight eating my pussy.” Kneeling above her, I smiled when she reached out to take my cock in her hand. “Let’s see if we can’t put this to good use now.”
About this time, Donna came out of the closet wearing a short silk number like she usually wore. And walked around Devon’s bed, as they were in an L shape configuration. But this time, as she crawled up into the upper bunk, I couldn’t help but notice she wasn’t wearing panties. Like I said, I wasn’t about to comment on it. Our relationship seemed to be working just fine, and she didn’t mind me fucking her roommate when she was there. Why screw up something that was clicking?
As Devon pulled me closer and began to stroke my cock, I noticed that Donna lay down on the top bunk. But instead of laying there face up, or turning to the wall like normal, she turned so she could look over the edge of the bed at Devon and I. She smiled sleepily at me and rolled closer to the edge.
Devon by this time had rolled over and gotten on all fours. She knew how I loved doggie style and she was really begging me to fuck her. “Come on, Chris,” she panted. “I need your hard thick cock in me. Fuck me, Chris. Come on, fuck me.”
As I started my rhythm in Devon, Donna’s legs parted slightly on the top bunk and she slid one hand down to her pussy. Her body was almost eye level with me and I had a great view as she teased a couple of fingers along the edge of her pussy lips.
(During my whole story so far, Lynn, my present day girlfriend had alternated rubbing my body, stroking my cock and balls, rubbing her own body lightly, and occasionally teasing her own pussy. When I got to the part about Donna’s masturbating to me fucking her roommate, Lynn wrapped one hand absentmindedly around my cock and began to work her own pussy a little more earnestly.)
“Oh yes, baby, fuck me!” Devon panted. “That hard cock is just what I want. Fucking me. Filling me. Stretching my pussy apart.”
Devon’s hot talk always got me going. I reached up and grabbed a handful of her short brown hair and pulled her head back. I could feel the tips of her fingers on my balls as she fingered her clit. I fucked her hard while I watched her roommate finger herself to the sounds and sights of me pounding Devon’s pussy.
“That’s it, baby. That’s it. Fuck me like your little whore. Take me. Fuck my pussy with that hard cock. Yeah, baby. Fuck it. Stretch my tight pussy with that big dick. Fuck me hard, Chris, FUCK ME. Yeah baby, that’s it. I’m cumming for you. Cumming on that thick cock.”
And she did. Devon’s orgasms were a thing of beauty. Panting, clenched teeth, fucking back for all she was worth, her hand a blur as she stroked her clit. And I almost always came with her. She was that fucking hot. But I don’t know if it was cumming twice already that evening, or my attention begin divided between Devon and Donna, but I just kept pounding in and out of Devon’s soaking wet pussy with no urge yet to cum.
“mmmm,” Donna mumbled to no one in particular. “That looks so good sliding in and out of your pussy. In and out...” And as she said it, she slid two fingers all the way into her own wet pussy and quickly back out. I could see the juices glisten on her fingers. Man, she must have been soaked. Her hand began to match the rhythm of my thrusts in and out of her roommate’s pussy, and Donna licked her lips.
I continued to pound Devon’s tight pussy. My balls slapping her clit with every hard thrust into her. She moaned and squealed with delight.
“Oh, baby. Yes. That’s it. Fuck me. Fuck me, baby. Fuck me hard. Ohhh. NNNnnn. Yeah. Feels. So good. Fucking me.” She panted.
As I quickened my pace once again for the onset of Devon’s orgasm, Donna began finger fucking herself with a third finger and rubbing her clit quickly with the finger tips of her other hand. She watched me intently fucking Devon, as she mumbled, “Nice cock. Fucking. in and out. cock in. cock out...”
As Devon wound her way up to another climax, I could tell Donna was on the verge too. Her breathing quickened and she rolled on her back to get better access to her wet pussy. She thrust her hips up against her hand, matching me thrust for thrust until she moaned a deep orgasm with all three fingers buried deep inside herself.
That was enough for me and I shot I load after load deep into Devon’s box continuing to fuck her hard until she came. Devon buried her face deep in her pillow and let loose a scream of pleasure, coming slowly down as I slackened my pace and fell in a heap beside her.
“Oh baby, that was wonderful!” Devon slurred as she covered my faces with kisses. “Thank you for tonight.” I nodded and kissed her back deeply.
By this time it was around 4:00 in the morning, and I needed to get a little sleep before my classes the next day, so I headed home to collapse into the bed.
“And that,” I concluded, “was my wildest evening.”
“MMmmmm,” Lynn moaned. “You were such a naughty boy. But that was a really good story. I would have liked to have seen you fucking Devon like that.” And with that she took her hand from where it had been playing in her pussy and licked her juices from two fingers.
“Mmmm, you’ve made me so wet,” she said, giggling. “Although I guess I helped a little.” And she winked at me.
“Look,” Lynn said, sitting up. “We’ve all done stuff that’s in our past, and we’ve gained experience from it that makes us who we are today. And I love who you are today. I’ve done things and had wild nights, too. But the important thing is that we love each other today.”
I breathed an inner sigh of relief that I had gotten this off my chest and Lynn was okay with it. I was able to share myself fully with someone I intended to spend the rest of my life with and that was a good thing.
And to be perfectly honest, I had gotten rather turned on at the end watching her play with her pussy. In fact, my cock was hard again and ready for action.
Yet, at the same time, did I have the same urge to know about her wildest night? Did I really want to open that Pandora’s box? Or was I content in the knowing of who she was today? But damnit, if that story hadn’t fazed her that much, what kind of stories must she have? |