I love math, and I’m good at it. It wasn’t my major, but in my first semester of college I took the standard calculus course everyone in science and engineering takes. I thought I was picking it up fairly well because I could do the homework, and spent more time on my other courses.
Then came the first test. We got them back on a Friday just after lunch, and I was shocked. As I stood there looking at the 63, nearly a failing grade, I heard the girl next to me say, “Looks like you got a little overconfident.” I hadn’t wanted her or anyone else to see the grade. She was a math major who had sat next to me starting with the second week. She tossed her shoulder-length brown hair back and looked up at me. Until now I hadn’t paid a lot of attention to her, even though there weren’t many girls in the class, or, for that matter, in the school.
Pam was not at all attractive. She was short, at least 100 pounds overweight, and had some acne left over from her earlier teens. Her glasses were thicker than mine. But for all that, she was pleasant and friendly, when I talked with her at all, and even more so now that she could see the lousy grade I had gotten. I found that odd; I would have expected she would gloat a little, or not say anything.
She showed me her test, with a 98 on the top. She said she had screwed up on one problem. I folded my test in half so nobody else could see the grade and said, in a low voice that conveyed my disgust with myself and wouldn’t be audible too far away, “I screwed up on nearly half of them,” and looked away.
I could feel her looking up at me and turned back to her. Her deep brown eyes seemed to search mine. “Do you want a little help? I used to do tutoring when I was in high school,” she offered, and touched me on the arm.
I looked back at her, and down; she was at least a full head shorter than me. My first thought was, “Great. She’s thinking of me like some dumb kid.” I said, “I don’t know, Pam. I think I’ll go back to my room and have a look at it myself.” I did that, and by dinnertime I was starting to think that maybe I wasn’t all that good at math. Everyone had told me college would be a different game, and now I was made painfully aware of just how different. The scary part was that one of my scholarships required me to maintain a 3.5 GPA or I would be out of there with nowhere to go. Literally. It was too late to go to an easier school, or a less expensive state university, and I had no home to which I could return to lick my wounds and try again.
I went down to the cafeteria at 6:00, my usual dinnertime, and Pam was at a table with her roommate and another student. She motioned me over, and since my usual group wasn’t there, I could hardly refuse and sit by myself. I put my tray down across from hers, since she had called me over, and sat down. I was glad she didn’t say anything about the test. She and the others talked about weekend plans and movies, and she asked what I would be doing. “I’ll be studying, and I have to work half a day tomorrow.” I had a job in the library, shelving books.
The other girls left and Pam reiterated her offer to help me with math. After a little consideration, I agreed to go to her room later and work with her. It couldn’t hurt, and she was very smart.
I spent another 30 minutes in my room after dinner going over one particular rate problem, and although I got the right answer I had to admit to myself that I didn’t really understand it. What got me was that I had done the assigned homework perfectly, but the test was much harder and the professor counted tests much more heavily than homework. I gave up and walked down the stairs, across the quad, up the stairs in the dorm where Pam lived, found her room, and knocked. She answered quickly, smiling. She was wearing a white blouse with the top two buttons undone. I could see the cleavage between her huge breasts, and that threw me off for a second. I’m a sucker for breasts, and cleavage is a big turn-on, although I didn’t expect to be turned on by her. I recalled that she had been wearing a sweatshirt at dinner, her more usual attire.
She invited me in and pulled her roommate’s desk chair over to her desk, motioning for me to sit. She got out the textbook and opened it to the end of the relevant chapter, where she picked out a problem similar to one I had missed, one that had not been given as homework. She asked, “What’s the first step in solving this?” And so it went for well over an hour, with her asking questions, gently correcting my mistakes, going back to where I got lost, never being nasty or scolding, even when I made dumb mistakes like getting the right number with the wrong sign. Some of my mistakes were due to nervousness. I wasn’t used to studying with anyone else, and especially not a girl with big tits. I solved the textbook problem and several others like it. I got it. After a while, I could solve even the toughest problems. I had filled four pages in my spiral-bound notebook with problems. I figured she must have gone to a far better high school than the one I attended.
Some time while we were working her roommate breezed in and put a few things in an overnight bag. She gave me a look I couldn’t quite interpret and didn’t seem at all surprised at me being there. Perhaps a knowing look? Maybe a little bit of a leer? As she started for the door she said to Pam, “See you Sunday. You kids have fun.” She smiled and was gone. Pam must have told her she had invited me up to study.
Pam explained that Lynne went home every weekend, and that she was probably eager to see her boyfriend. “We know what she’s going to be doing,” Pam said with a smile. I let that remark go, not knowing how to respond. I had a guess, and it involved biology, not math.
We finished the last problem and she closed the book, then turned to face me. “You’re really smart. You just needed a little practice.” Her face flushed a little. “And so do I.” Her chubby little hand gently touched my inner forearm near the elbow.
I was a little confused. Her? Need practice? She noticed my blank look and continued. “I didn’t invite you up here just to do math.” Oh. I thought she had. “You didn’t?” was all I could manage.
“No, silly. I’ve always liked you, from the first day of class. You just seemed a lot nicer then the other people here, and your voice, when you spoke up in class, was wonderful.” With that, she leaned over and kissed me on the mouth, not too quick but not lingering, and pulled back. It felt good, but I was confused. She smiled. “You’re not used to girls coming on to you, are you?”
“No. This is kind of a first.” I still wasn’t sure where this was leading, what she wanted, but even though I was a nerd, I was starting to catch on.
“You don’t have a girlfriend, do you? Someone waiting at home to see you on holidays?” She knew I spent the weekends on campus, but not why. My personal life was a complicated flaming mess, and college was my escape. That was all the more reason to do well. None of that was any of her business. I had been seeing someone, but she had dumped me in July, a month before school started, which didn’t surprise me. What had surprised me was that she ever went out with me to begin with. This was also the time things really fell apart at home, such as it was. “No, no girlfriend,” I managed. Her intentions were becoming clearer.
She got to the point. “Jack, I know I’m not your idea of gorgeous, but I think I can be a lot of fun.” And she kissed me again. I could see down the Grand Canyon of her cleavage as she leaned in. She was wearing a low-cut bra. I gave in to the kiss, enjoying it this time. When she pulled back she said, “You may not know it, but you’re hot. You’re, what, nearly 6 feet of solid muscle? I don’t know how you got that way, but all of the girls notice. And you know how to kiss.”
“How do you know I know how to kiss?”
“I’ve had a few kisses, but more than that I’d rather not say,” she replied. I didn’t press the point.
I turned that over in my mind. I was in top shape, between hikes and camping with the Boy Scouts and my after-school job unloading trucks, but I never thought of myself as a jock, or hot. I didn’t much like sports. I was a nerd. I also thought, “All of the girls? Like all ten of them?” There weren’t many at that school, and I didn’t feel like I got noticed at all. There were plenty of guys who were better looking than me.
“So you don’t have a boyfriend waiting at home?” I teased. She got a little serious, a little annoyed. “What do you think? If I did, you wouldn’t be here.”
She went on. “I said I needed practice, and you’ve figured out I wasn’t talking about math. I was born with my vagina closed up, and it had to be surgically opened. And kept open. So my mother used dildos to do that, and when I was old enough I used them myself. I got to really like the feeling of something inside me. I guess I’ve had more permission to explore myself than most girls. So I take care of myself a lot, but dildos can take me only so far.”
“So you want me to take your virginity?”
“I’m not exactly a virgin, in the sense that my hymen is long gone if I ever really had one, but I’ve never had a cock in me.”
I had a huge approach-avoidance conflict. She had practically asked me to have sex with her, and I was a virgin. On the other hand, at first blush she didn’t seem like someone I wanted as a girlfriend, although her personality had been growing on me. She was really nice and easy to talk to. And for an eighteen year old male, sex trumps nearly everything. On the other other hand, although I knew the mechanics of sex from watching porn and reading, I had no actual idea of how to proceed. My high-school girlfriend and I had done a lot of kissing and a little clothed touching, and she let me suck her breasts a few times before she dumped me, but nothing more than that.
She saw my hesitation. “Look, we don’t have to be all kissy-face and holding hands in public. But I do like you, and I can take good care of you. And I’ll get you through math, although you probably don’t need much help if you work a little harder.” She leaned in for another kiss, this one deep and sensual, our tongues playing. I felt her hand behind my head, and another stroking down my chest. When we finally broke, she had unbuttoned two more of my buttons. I was rock-hard, my cock straining at my jeans. I had to adjust, but was too embarrassed to reach down and do it.
“Let’s go sit on the bed,” she suggested, and got up, turned off the desk lamp, and walked the four steps. That let me adjust my aching cock. I joined her, and I’m sure she noticed the bulge in my jeans. We had another hot kiss. My hands stroked her nipples through the cloth, then went for the buttons on her blouse. When we pulled away, she finished unbuttoning my shirt. She took off her blouse and bra, revealing two enormous sagging breasts. Big, perky nipples sat in the middle of small aureolae, inviting. I leaned over and kissed and sucked first one, then the other. It was awkward but fun and she moaned with pleasure. It was pretty clear she liked it, and she said it was the first time anyone had ever done that. When I came up for air I said, “Let’s undress each other.” Yes, a little late for that idea, but I wanted to finish the job and get a look at her.
She agreed and stretched out. I unbuttoned her pants and she lifted up to let me slip them off. Then the panties, which I threw to one side. And there she was, naked and mine if I wanted to take her. I could see the patch of dark brown hair pointing to her pussy, but nothing more. Her thighs were huge and covered her slit.
“Your turn,” she said. She stood up and removed my shirt, then gently pushed me back on the bed. She unlaced my running shoes, took them off, and took off my socks. She stroked my cock through my jeans, then unbuckled my belt, unbuttoned and unzipped my jeans, and slid them off. My briefs had a spot of pre-cum on them. She took them down carefully so as not to bend my stiff prick, and gazed hungrily at what she saw. I’m not huge, but at just over six inches and fairly thick, I’m somewhat bigger than average. She took off the briefs and leaned over to suck the tip a little. She asked about the wet spot. “When guys are turned on, we get a little wet, just like girls.” “Oh, pre-cum,” she said. I later learned just how much she liked erotica, but somehow that detail had escaped her. She tossed the briefs on top of her panties.
“So here we are,” I said. “But I don’t have any condoms with me, and I don’t want to get you pregnant.” I was giving her a chance to back out, but I was really giving myself that chance.
“Don’t worry about that. I had a lot of problems with periods, so my mother got me on the Pill when I was 15.”
“Wow,” I thought. “My first time and I get to go in bareback.” What I said was, “That’s great!”
She moved to lay on her back with her ass on the edge of the bed and brought her legs up high and spread them wide. She was surprisingly flexible. I took a good long look at her pussy. It was a little different from what I had seen in porn. Her inner lips were small and her clit was tiny. Her huge, hairy outer lips were swollen and parted. I got on my knees and gave her pussy a long kiss. I liked the scent, something I had only read about. It’s hard to describe, a little musky, maybe a little sharp. She tasted salty, too. She moaned as my tongue found her clit. In my naivete I thought that constituted foreplay.
“Jack, have you ever done it before?”
“Done what? Sex?” and my voice trailed off. I had been found out.
“I didn’t think you had. That’s part of why I picked you. Well, you know I haven’t either. Just the toys.” That made me feel better to hear her say it, even though I already knew that.
I stood up and she took the opportunity to turn around to lie full length on the bed, and brought her legs up. I knelt between them and stroked her with the tip of my cock, starting with her clit and ending at her opening. She was soaking wet, ready. I pushed in, slowly at first, then buried my length up to the balls in her. What I later came to call the “shock of entry” was amazing, that feeling when the tip goes into a wet, ready vagina. She moaned and looked at me, her eyes wide, and leaned her head up. I leaned down and kissed her, savoring the moment of having just entered a woman for the first time. She was wet and tight, and felt nothing like my own hand.
When a man has sex for the first time, there are at least two things that can go wrong, and often do. The first, inability to get or stay hard, was obviously not the problem. What happened to me was the other one: premature ejaculation. I made exactly four long strokes in and out of her and came, shooting cum deep into her soaking cunt. I panted into her ear, “Oh my god, Pam. I’m sorry I came so fast.” But I didn’t pull out, and I stayed fairly hard. I felt her cunt muscles squeeze me, and she said, “It’s okay. Just hold me.” I raised up on my forearms and kissed her. I was embarrassed beyond belief. It was a good thing she couldn’t see my red face in the dim light.
I moved in and out a little, and after a few minutes I was good and hard again. She moved with my rhythm, and after just five or six minutes, she came. It was amazing. I felt her cunt gripping my cock, heard her ragged, gasping breathing, felt her shudder and her head moved from side to side. I kept stroking her despite the feeling behind my balls telling me I could cum again, letting her enjoy her climax. But then I thrust deep into her and stopped, and let her orgasm trail off. She held me tightly and whispered, “That was incredible, Jack. I never would have guessed. But I did fantasize.”
I lifted up a little and kissed her, still not moving. I wanted to stay in her forever. But she moved her hips, and I started moving again, but managed to hold off cumming. She panted and whispered, “Fuck me hard, Jack.” It was incredibly hot to hear, and I did, thrusting in and out of her tight cunt and making her cum once more. I stopped moving when I again felt the telltale sensation behind my balls. “Why did you stop?” she asked. I said, “It feels better if I don’t cum so fast, if I let it build.” That was true, something I had learned when I started masturbating at age 13, but I also didn’t want my first time to be over so quickly.
It had never occurred to me, despite porn and what I had read, that women needed, really needed, sex as much as we men do. They just have a different psychology about how they get it and who they do it with. And they need cum, too.
I started stroking in and out, long strokes with the tip almost out, letting her pussylips kiss it, then in until my balls felt the wetness of her cream and my first orgasm. She came again, and again, moaning softly so nobody who might be walking by in the hallway could hear, and whispering, “Fuck me harder. Cum in me, Jack. Cum in my cunt.” That, her tight wet grip on my throbbing cock, and my thrusting pushed me over the edge. I felt the uncontrollable throbbing behind my balls, the searing pleasure on the tip of my hard prick, and I pumped another hot load up her luscious cunt, moaning, “Oh God, Pam, I’m cumming.” I felt her tighten on me and heard her moan; she had cum too. I collapsed on her and kissed her neck.
I was still somewhat hard when I pulled out of her and lay back. She snuggled up against me and we had a long kiss. My fingers went to her nipples to pinch and stroke them. They were hard little pebbles. After a while she sat up and started playing with my cock. “I’ve never really seen a cock before,” she said, as she stroked up and down, or cupped my balls. “Only in porn, but the focus is always on the girl or on the guy getting sucked, except in gay porn, and that’s just weird.”
I spread my legs a little to give her easier access, and she kept stroking. “So what do you think, now that you have a real one in hand?”
She ran her fingers over my hairy balls and down between them, as far as my anus, and gently stroked around it before coming back up to the shaft and tip. “It’s beautiful,” she purred. “Way better than I fantasized.” She ran her finger around the ridge. “And you’re huge. I’m glad you’re good at math, or you would have had a career as a porn star. I would have had to watch you fucking other girls.”
I laughed at that. “Thanks. You’re pretty amazing yourself. From what I hear, most girls don’t have a very good first experience of sex. It sounded like you did.”
“Well, I had a lot of experience with it before you, but only with my toys. I knew what turned me on, what penetration felt like. But I never felt anything like the sensation of you holding me down or sucking my tits, and nothing ever like you cumming. That was beyond incredible.”
“Even the first time? When I didn’t even give you time to warm up?”
“I was warmed up before you got here, if you know what I mean, and that was so hot. I felt wonderful, knowing I could make you lose control. You don’t lose control very often, do you?” she said, smiling. She was still stroking my wet cock, playing with it, sometimes looking at me, sometimes at it. She sometimes leaned down to suck it, a little tentatively. I was almost hard again.
“No, I don’t, but you sent me right over the edge.” I knew she wasn’t just referring to sex, but I ignored the implication and smiled back and said, “So you could feel me cumming in you?”
“Well, not exactly. But I felt you change your stroke, and it felt like your cock got even bigger. And then you went all the way in, hard. Incredible.”
“You felt really tight, like you were gripping me inside.”
“I was. And then I felt your cum dripping down my ass. You must have been saving it up. When was the last time you took care of it yourself?”
“A couple of days ago.” That question embarrassed me even though I did masturbate, but I gave her a straight answer.