Teacher/Student Boundaries

My name is Jay and I am currently a senior in college. I’m 21, going on 22, and a Criminal Justice major. I don’t consider myself to be in great shape, but I’m not big either. Maybe you could say I’m average in comparison to today’s society. I’m Latino, military style hair cut (high and tight), tan skin complexity, brown eyes, and dark brown hair. I’m fairly muscular, not as toned as I could be, but I can handle my own as I work for the local County Sheriff’s Department as a Corrections Officer. I love my job and women love me–gotta love the uniform. I’m a social drinker, engaged, and still live at home while in school. However, I work 2 jobs, go to school full time, and support my mother (disabled), while also making car and insurance payments, rent, etc. So, even though I live at home, I’m still very much responsible for being 21.

Until recently, I’ve been quite happy with my life and where I’m at. I’ve been with my fiancee for 4 1/2 years and we’ve been engaged for 1 1/2 of those. However, for the past year or so, I’ve noticed I haven’t been as interested in my fiancee. Our sex life has severely diminished and I don’t feel as attracted to her as I used to be. This is where things get a little interesting.

Last semester, Fall of 2008, I was taking an English class to fulfill my requirements. My professor, Sara, was a real knockout. A blond bombshell if you will. She’s tall, skinny, long blond hair, pouty lips a little, long legs, a 38 C rack (I know what you’re thinking, I’ll get to that), and a nice ass, although flatter than I’d like, but I’m not complaining. She’s got those blue eyes that I could stare into for hours. Oh, and she’s married, has been for 17 years. What I haven’t mentioned yet, is she’s 38. At first, it was just that innocent crush a male student has on his professor. I’ve never been lucky enough for something like hooking up with my professor to happen.

We’d known each other from both of us being at the school all the time and in passing. Her husband also works there, as an activities coordinator and professor. He’s a real dumbass and douschebag. Anyway, half way through the semester, I get this job as a Corrections Officer, but need to take off 5 weeks from school for training. Not a problem, I work it out with all my professors and Sara is allowing me to email her my homework each week. I’ve always been a pretty flirty guy, regardless of being engaged. So, naturally, I throw in the occasional line when I email her my homework. She shrugs it all off like a professor should do. Well, as the semester draws to an end, my emails begin to get more and more flirtatious. I’ve broken through her walls a little, but she tries to keep putting up a guard. Slowly, she begins to flirt back, not noticing it. The semester is over. We continue emailing and flirting. I find out she’s been getting abused by her husband and is filing for a divorce. She knows I’m engaged, but not totally happy.

The new semester starts up, we’re still emailing and I’ve started going in to her office a little here and there. I’m bringing her coffee. Within a couple weeks, I’m going in every Tuesday and Thursday to see her, bringing her coffee. She’s looking forward to seeing me each week and I with her. Now, we’re talking on IM and over the phone. One night, I was willing to press my luck…

Jay: I’ve had a huge crush on you since I’ve known you

Sara: Why?

Jay: You’re beautiful! I’d love to kiss you, I just might tomorrow…

Sara: lol. I might just let you.

Jay: I love it when you wear those skirts to class and sit on top of that desk (I sat in front of the class). I often try to look up them, but to no avail

Sara: That’s too bad. You might be surprised. I don’t wear panties when I wear skirts, just stockings. Sometimes when I wear jeans, I don’t wear any type of underwear.

The next morning is Tuesday. I’m on my way into her office, coffee in hand. I sit in her chair. She gets up, comes over to me and hugs me for the coffee. My heart is pumping. I pull away and pull her back in and kiss her. Surprisingly, she kisses back. The next thing I know, our tongues are dancing together and this one kiss is so passionate and long, that I remember nothing else from this morning. From now on, every morning I see her is like this. We’re making out. One day, I decide to get a little riskier and slide my hand up her shirt, massaging her tits. Kneading them, pinching her nipples between my fingers.

We’ve talked more and more. We’ve begun falling for each other. We have decided that we cannot have sex. Through everything, we’ve been trying to find boundaries, but have been unsuccessful. Sara told me she used to be a wild girl when she was younger, to which I replied, “i’d love to bring that girl back out.” It has become a challenge for me. We both have a day off. My fiancee is working all day. Her husband is at the school all day. We’ve arranged for me to come down for a couple hours and just cuddle. I get down there and we do just that. Her 3 kids are at school. She’s dressed in her pj’s, with no panties on. I know we’d decided that we weren’t going to have sex, but I just had to feel that pussy. We started making out, lots and lots. I’m feeling her up all over.

I move in between her legs and pull her pj bottoms down. Heaven. I can see her juices glistening off her pussy. She’s cleanly shaven. I look into her eyes and ask her if she’s willing to go further. I’ve never been a fan of eating pussy. I don’t know if it’s just because I’ve never had a pussy good enough to eat or if I just don’t like the taste. Well, I’ve learned it’s always been the female’s fault. I went down on Sara with a fury. My head was buried between her legs while her legs were wrapped around my head, squeezing it. I start rubbing her clit immediately while my tongue is licking up and down her slit. I start sucking her clit a little, nibbling on it and fingering her. I slide 2 fingers in at first. Still sucking her clit. I pull them out and move back up to her and kiss her ever so passionately. She savors the taste of her own sweet nectar. I stare into her eyes again, sit up onto my knees, spread her legs further and guide my raging cock to her waiting pussy. I slowly begin to penetrate her, feeling inch by inch being engulfed by a hot, juicy, never-ending tunnel of pleasure. The next thing I knew was I was fully in her, up to my balls. I pull out and thrust back in. We get into a rhythm and I can hear her juices squishing between our bodies. I pull her legs up onto my shoulders and keep thrusting into her, feeling myself getting deeper and deeper. I can hear her moaning my name. By now, she’s had multiple orgasms. We keep going and I push her legs up further so her knees are close to her tits, making her ass rise slightly off the bed. I keep pounding away, feeling my pelvis hit hers.

I start to feel the familiar feeling of my balls tightening and I know I’m close. I tell her, “Sara, baby, I’m close. I want to let it loose inside you. You want to feel my hot, sticky cum explode in you baby?” “Mmmm, yea. Let it loose in me Jay. I want to feel your cum in me,” she says. Here it comes, and the next thing I knew, I was flooding her pussy with my man juice. I empty myself inside her, letting her pussy milk the rest of my cum out of me. Exhausted, I roll off to the side and we cuddle for a bit. About a half hour later, I’m still semi hard and Sara starts playing with my cock again. I can’t think of many times where I’ve been able to go again after cumming once already, especially not so soon. She gets me rock hard again and climbs over top of me. She takes hold of my cock and lines it up to her slit and slams down onto it. Sara starts bouncing up and down with me under her, thrusting up to meet her hips. She still has cum left over inside her, which is now all over my cock, making a puddle at the base. I’m loving the feel of my cum coating my cock as it slides in and out of her. Within a half hour, we’re both sweating and she’s had many orgasms. Each time she climaxes, I can see her eyes close, she takes in a deep breath and holds it. I feel my balls tightening once again and without warning Sara, I shot my load up inside her. This woman is unbelievable. After I release, she keeps bouncing, without a care in the world about how sensitive I am. Eventually, she rolls over.

A half hour later, I’m leaving, tired out like crazy and ready to crash. She’s ready for another round. My hips are hurting and I’m too exhausted. I’m 21, she’s 38.