I did some dating in high school but never dated any girl very long. I don't know if it was me or them, but for whatever reason, the relationships just never went beyond casual dating.
I had plenty of friends who were going steady, hooked-up tight, and just about all of them were having lots of sex but me, well, again casual dating did provide a few hand jobs now and then along with some nice boob action from several girls, even some memorable blow jobs.
But, well, I wasn't a virgin when I went off to college, I'd gotten rid of my cherry when I was seventeen and a senior in high school to a girl, Melissa Robinson, who was easy to get into bed. Our relationship wasn't serious in the least, I wanted to have sex for the first time and Melissa loved sex. Pretty much all you had to do was ask.
Well, it was pretty good, she had a pretty nice body and all and she really knew how to use it. So, I did go off to college with some experience at least.
As many have found out as well, college life and college girls can be much more open and free than what we all had in high school. I really think a lot of the change that takes place is due to the girls. Once they leave high school and go away to college, they, many of them, let go and begin to have a good time. A really good time.
That was certainly what I saw and I took advantage of it just like most of my buddies.
There was one girl, however, that I met when I was in my junior year, she was a sophomore, and we really seemed to hit it off really well. Diana Dolan, like me, was also an English major with an Education minor, we both planned to teach after graduation.
Diana was really pretty and I soon found out that she had a lovely body that she enjoyed using well and often. I teased her about being "DD with the B's and C's" as a take on her name's initials, her general grades, followed by her bra size.
It was after a few months of dating that we began discussing more permanent plans and soon after that we became engaged. My parents thought the world of her and when I met her mom, we really connected so it was looking like it would be a marriage made in heaven, as they say.
Everything was wonderful all the way through my graduation and into my getting a teaching job nearby as Diana began her final year. Then, we both began to see that we really weren't meant to be together and decided to end our engagement and go our separate ways.
It had been about a month after we'd made our decision, on a Sunday morning as I was sitting at my kitchen table reviewing lesson plans for the weeks to come, when my doorbell rang.
I hopped up and looked through the little security peephole and there was Diana's mother, Judy, standing in the hallway outside my door.
Now, I had always gotten along with Diana's mom really well, she was nice and fun and we always seemed to hit it off.
I knew her mom had been disappointed when we called off our engagement because I overheard her on the phone with her mom telling her after we had come to the decision. Her mom was more upset than we were, it had seemed.
So, I swung the door open and welcomed her in.
"Oh, Kenny, I hope I'm not bothering you this morning but I was in town and had some of your things that were still at my house," she said, handing me a grocery bag full of clothes.
"Oh, sure, gee, thanks, come in, I've got coffee," I said and she stepped inside and we went to my kitchen where I got a mug down. As I turned back to her, she was standing there crying, "Oh, Kenny, I'm so sorry you two have parted ways, I'd so wanted you for my son-in-law."
I stepped over to her and hugged her to me as I felt her trembling as she sobbed a bit. I held her for a minute or two until she'd calmed down when she said, "Oh, I really should be going, Kenny, I've disrupted your morning enough, I'm afraid. I really just wanted to say goodbye."
I'm not sure exactly why but I pulled her back to me and kissed her, perhaps a little harder than I'd meant, though maybe not. It was then that I felt her tongue slip between my lips.
I might have been a little surprised but I was also rather pleased and opened my lips so we could tongue-kiss which it seemed we were both enjoying as we held each other that Sunday morning.
Without thinking much about it, my hands had roamed downward and were on her butt squeezing and pulling her middle into my middle which, in the long, male tradition, was expanding outward.
She felt soft and warm and nice, Diana's mother was a pretty woman, trim and shapely, I think Diana had told me her mom had turned forty only a couple of years ago, so she was certainly not old by any means. She felt quite nice in my arms, I can tell you that.
As we kissed, there was no way she could not have been quite aware of my erection making itself known and when we separated, we just kind of stood there and looked at each other.
Then, quietly, she asked, smiling up at me, "Kenny, would you take me to your room?"
The words went directly to my cock. I've told you my exe's mother is a pretty woman and kissing her filled me with sexual excitement like I hadn't felt in quite some time. She was a small woman and nicely curvy and I took her again and kissed her in a very non-almost mother-in-law fashion now with my hands down easing her skirt up to feel her ass in her panties.
We kissed another minute, then I said, "I'd be very happy and very proud to take you back to my room," and took her hand and led her down the hall to my bedroom, where, thankfully, I had straightened the covers earlier.
As we went in, she took me again and we kissed as our hands moved on each other working to get one another's clothes undone.
I had her blouse open and had reached around to unclasp her bra as she got my pants loose and pulled down to my knees. She stepped back and was quickly out of everything but her panties and I stood there in just my boxers as we hugged again and kissed some more, this time with her hand down under my waistband feeling my hardness as my hands fondled her nice warm breasts.
"I'm not as young as Diana but I hope you'll be happy with me," she whispered as I looked at her lovely body. She was older, yes, but she still had an attractive figure with nice breasts, full with just a bit of under curve. Her nipples were very hard and erect with large pink nipples that I was enjoying rubbing.
"I've got to say that I'm just really excited to have you here like this. You're really a very pretty woman and I find you very desirable. Very hot," as I kissed her once again.
I took her hand and led her to the bed and swept the covers back. She got on and pulled off her panties while I dropped my boxers to the floor.
"Mmm, Diana, of course, had told me how wonderful you were in most things, Kenny, but she kept your lovely manhood to herself. Can't say I blame her," she said as I crawled up next to her and we again slid into each other's arms.
"I know I'm taking you from your work, but I really just don't care," she said as she moved over me kissing me while her hand moved up and down on my cock.
My heart was pounding and there was a throbbing in my cock, something that never happened when I was having sex with her daughter. I was so aroused by this forty-something woman, probably much of it in my mind, the taboo nature of what we were doing but, well, it was so hot and sexy to have this naked woman in my bed I could hardly contain myself.
I'd never been with anyone much older than I was, this was a first for me, especially a woman not far from twice my age.
"Well, I really was just polishing up my lesson plans and the truth is, I've got just as much time as you have, I really love having you here with me like this."
She rubbed her body on mine, telling me, "Well, if we have the time, Kenny, I'd make you a very happy man."
"Oh, for that, I surely have the time," I told her as her tongue went back in my mouth.
Then she pulled back from my face to say, "For me to make this the best for you, you have to do something for me, you have to tell me whenever you get close to cumming. Can you do that?"
"Yeah, I guess so, nobody's ever asked me to do that before. This is some kind of thing you like to do?" I asked her.
"Oh, yes but you'll be the one that really loves it," and she got off me to kneel beside me, taking my cock in her hand and licking around the head as she smiled up at me. Then she tilted her head to lick up and down my shaft as her fist twisted around the head.
Next, she stood up over me, straddling me as I watched her lower herself down, reaching to hold me steady to put the first inch or two up inside her. But that was all. Then she began moving around in a circle while also going up and down on me but just with the top third or so of my cock.
"Mmm, oh, that's good, really good," I moaned.
"Tell me if you're close, okay?"
"Mmm, it's good but no, not yet."
My hands were on her breasts as she fucked the end of my cock while squatting over me, then she pulled up a little, reached down and swiped the head back and forth in her pussy's wet slit, then around and around in just the very front part.
Then she got down and sat cross-legged next to me leaning over to suck the tip again, then, leaving it wet with saliva, she held it with one hand and rubbed her palm around and around just sending my heart rate skyward.
"Mmm, that's getting me close. You wanted to know," I gasped as she lifted her palm and just barely touched the tip with her index finger, just a little.
"What is it you're doing to me?"
"I'm just making it last as long as we can, it really gives me the best orgasms that way and I think you'll like it, too. Every guy I've done this with has wanted more."
"Mmm, I'm sure willing to try it, it's great so far."
"Some men don't have the patience but I think you'll see at the end that it was worth it."
"Yeah, let's go for it. I'm so glad you came by and so glad you didn't have to rush off," I laughed and so did she as she slid her lips over the head of my dick and left it wet. Then she circled it with her five fingertips and began twisting her hand back and forth as she moved so her nipple was near my mouth.
I had reached my hand down between her opened legs to begin rubbing the wetness up and down. She, like her daughter, was completely shaved. I pushed a finger inside, something I'd found out early on that her daughter liked so much and it seemed from the soft moans it produced, that she liked my fingering as well.
I knew that what she was doing to me was wonderful. I had learned the valuable lesson that sex, like so many things, is often best taken slowly but this was really erotic. I had never been so highly aroused in my life. She was just keeping me right on the edge of cumming and I had no idea how long she would continue like this.
"Mmm, I'm getting close again," I told her as she stopped twisting her fingertips around the crown of my dick to begin just slowly, very slowly circling the head with the gentlest touch of her fingertip. That was almost more maddening as I told her again that I was near cumming.
She simply let go of me and leaned close to blow little breaths of warm air over my cock causing it to jump and twitch. It was kind of funny to watch in a way but it did feel nice. I now began working a second finger up in her as she shifted slightly giving me better access.