Regrets and Fantasies

As you get older you find yourself reflecting on your past. And then, a few years after that you start thinking about regrets. I don't have much in the way of regrets, but I do have quite a few incidents of missed opportunities. Not coincidentally, all of these missed opportunities have to do with sex.

So I've decided to create a series starting with the actual stories - up to the point that the opportunity was lost. And then, I let my fantasy take over. Here is chapter one.

Chapter One starts at the University of Vermont in 1973.

Jill Miller was famous on campus, at least among the UVM boys. She worked in the Student Center Student Affairs office. Most students had, at least, one reason to go there over the course of four years. More often than not Jill was the first person they would meet at the front desk.

Jill was gorgeous. A classic California blond (That a beautiful California blonde ended up in Burlington Vermont truly stretches credulity but it's true ). She was tall, somewhat slender and never wore a bra. The first things most male students noticed about Jill were her nipples poking through her UVM polo shirt. After a bit of ogling they would move on to her classic beauty. Her full lips, light blue eyes, her long blonde hair and perfect hips.

After I graduated I chose to stay in Burlington and got a job as manager of the university print shop. I had worked there part time over my last three years in school. When the manager position opened up I jumped at it. Having a decent full time salary in "college town" set you aside most of your peers.

A couple of months into the semester Jill, two other women from Student Affairs and I would meet to play scrabble during lunch hour in my office. There was always a lot of flirting among us. Jill was the only unmarried woman among them. Her flirting seemed to be more salient than the others. Nevertheless I saw it as just good natured banter.

When I started seeing a senior from the University her overtures heated up. Still, I considered it as benign repartee.

We often talked about how much we loved watching "The Wizard Of Oz" during its once a year airing.

"You should come over and watch it on my new TV." She said in what I perceived as loaded invitation.

"That would be great." Even though I knew that I probably wouldn't go and risk the indignation of my girlfriend.

"Great. I'll start making plans." She said.

On the night that the movie was scheduled my phone rang.

"Are you coming over?"

"Huh?"

"The Wizard Of Oz, it's on tonight."

"I'm sorry, Jill. I don't think I can come over. Amy is the jealous type and this would make her crazy, Who else is coming?"

"Just you and me."

"She definitely wouldn't like that. Although I think I might really enjoy it."

"Oh fuck Amy. She's not even here this week. Besides we're only watching TV."

"I just can't."

"You can. I got a bottle of Jack and a couple of joints. And it will look amazing on my new 25" TV."

"I'd really love to, but I just can't."

- - - - - - - - - - - - - - - - - - -

This is where the true story ends. Now my fantasy will take over.

"Kenny, come on. Please?" She was almost begging.

"Well, what the fuck. What time does it start?"

"8:00."

"I'll be there soon!" Just saying that started to make me get a little hard.

I knocked on the door of Jill's house. It was one of the many "rental" houses in Burlington. A bedroom, living room and eat-in kitchen.

No answer. That's really strange. So I knocked again. Jill opened the door wearing a blue men's Oxford button down shirt and a pair of maroon gym shorts. Her hair was damp and she was holding a towel.

"I'm sorry, Kenny, I was in the shower" I tried not to be too obvious as I noticed that the to four buttons of the shirt were undone. "Come on in. You want a drink? I've got some Jack Daniels."

"Yeah, that would be great."

"How do you take it?"

"Straight up is good."

"Really? Me too." She said.

She went to the kitchen and brought back a bottle and two glasses. She put the glasses on the wire spool that acted as a coffee table in half of the apartments in the area. As she bent over to pour the whiskey her shirt gapped enough for me to see her left breast.

"Here's to Amy." She said laughing as she raised her glass.

We both took big sips. Then she leaned in and gave me a big, wet kiss. I responded by gently sucking her bottom lip. As we kissed I reached into her shirt and did what a couple hundred UVM boys had thought about doing.

Her breasts were a little bigger than I expected. Still small but they filled my hand as I cupped them. As I brushed against her nipple she moaned just loud enough to let me know that she liked it.

Then, pretty abruptly, she pushed me onto the sofa. She started kissing again but now she was rubbing my cock over my pants. It was erect before, now it was whatever comes after erect.

"You're not fooling around. Are you?" I was still a little stunned at how fast this was moving.

"I've been wanting to do this for a long time, Kenny."

She undid my belt, unzipped my pants and pulled out me cock.

"Holy shit! You are really big!"

(Of course it's big. This is my fantasy after all)

"I hope it's not too big." I chuckled.

"Well, we'll see."

Right away she started sucking it. Only the head and another inch or so. She was going pretty slow up and down the top of my penis.

Then she stopped sucking and started stroking my cock. Up and down, making sure to stroke the head on her way up.

"That feels really good, Jill." I said to encourage her.

Then she started stroking with both hands. That was certainly something new. Faster and harder. I could feel that an orgasm wasn't to far off.

Then she went back to sucking. And reaching down to cup my balls. I've never really liked that so much, but she was actually reaching for spot in my balls where you can feel the shaft of my penis. She was rubbing two fingers there while she was sucking my dick. This was a new erogenous spot I never knew about. This really enhanced her work on the other end of my cock. Then she went back to stroking me. This time harder and faster. Every couple of minutes she would stop and start sucking again. Great technique. Then back to jerking my dick. Her free hand had worked its way the spot below my balls and above my ass. She was pushing up on it and once again i was having more arousal. Now she was jerking my cock really fast and pushing on my taint. I was ready!

"I'm about to cum."

I could feel it building. Just when I was about to come she started sucking again. Wow! That worked!

"How did you ever learned to do that? That was the best blowjob or handjob, whatever, I ever had."

"A lot of practice. A lot of practice, Kenny." Then she spit my cum onto her towel. "I hope you don't mind. I really don't like swallowing."

"That's funny. I never got this swallowing thing. I absolutely don't care what you do with it AFTER I cum."

Then she told me that she had a gay friend in Santa Monica who taught her how to suck cock.

"Well he taught you really well. But it's really funny because I had a lesbian friend who taught me how to eat pussy."

I was about to pour another glass when I just decided to drink it straight out of the bottle. Two big swigs and I was ready. Jill was lying completely naked on the couch. Jill's body was gorgeous. She was a real blonde. Beautiful pale skin and her pubic hair (don't forget it's 1973) was a kind of dirty blond color. Her breasts were not as I imagined them. I had pictured small tits, pointing straight out with nipples on the end. But her tits were bigger and rounder. They dropped down and back up with the nipples on top pointing slightly upward. These were award winning tits.

"You know your body is fabulous. Just perfect and I love your tits!"

Then without wasting any more time I went right to sucking on a nipple. Lightly at first but she made it clear she liked it harder. I had no doubt that she was really loving it.

Eventually I worked my way down to her pussy. I was kneeling on the floor with my head between her legs. Just the smell of her pussy was bringing my cock back to life.

I started by kissing up and down her inner thigh. While I was doing that I let my hand brush over her outer lips. Jill's assortment of moan's, sigh's and breathing was giving me all the direction I needed.

Then I began exploring her vagina. I lightly fingered her slit up and down. Her pussy was very wet. Each time I got to the top I would rub her clitoris very lightly. I spread her outer lips and started licking her pussy. I slowly inserted my middle finger into her but only an inch or so deep. With her outer lips spread I could feel her inner lips. They were very hard and Jill loved it as I rubbed them up and down.

Finally it was time to get serious. I was teasing her clit with my tongue. A lick here, a flick there and then I'd stop. Then I started flicking her clit with purpose. Her hips started rocking and her breath would stop then begin again really loud. I could feel her get close so I stopped.

"Oh please, Kenny. Please don't stop."

I started up again. This time I squeezed her clitoris to fully separate it from its hood and started sucking it into my mouth. At the same time my finger was moving slowly in and out of her pussy. I was feeling around for the g-spot (I don't know if sexual science had identified the g-spot in 1973 but again it's my fantasy). Then I stopped again.

"Oh my god. Please, please, please." She begged.

"Ok."

Once again I was sucking her clit and pushing on her g-spot. No more teasing. This was it!

"Oh yes, I'm cumming, oh yes, yes."

And she came! And came! It seemed to last several minutes.

When I finally looked up, her face had a look of total pleasure. Her body was dripping with sweat and her pussy was dripping with fluids.

"That was so good. I can't believe it. You are amazing."

Just as she said that I got up from between her legs and started to thrust my dick right into her pussy. I had forgotten how big my cock was, I quickly slowed down. She was very wet and I knew I could get it in if I went slowly.

It didn't really take that long. In a minute or two I was pushing into her pussy. Then I hit something and she responded with an "ouch". I tried to be careful but it happened a couple of times more. I assume I was hitting her cervix.

"That monster of yours is too big for missionary fucking. Let's switch positions."

So we got up. I lay flat on the couch and she climbed into a seated position. Then she lifted up and slowly lowered herself on my penis. It was good.

"Oh it feels so good now. It's so big it's rubbing everything in my pussy."

She started moving up and down on my shaft and I was watching those beautiful tits go up and down. Then I reached up and started diddling her clit. It was still free of the hood. My rubbing was doing what was expected. It didn't take long for either of us to get aroused.

"I think I'm gonna cum." Jill said.

"Yeah, go for it." I replied.

Then she started cumming. I caught up right away. It was an incredible sensation to be cumming at the same time as this thing of beauty. I continued a rub her clit and even after cumming my dick was big enough to give the appropriate amount of friction and she came again.

We went into the shower and washed a lot of funk off our bodies. While she was washing my genitals my dick became erect again.

"Are you ready to go again?" She asked.

"No I'm afraid I'm done for awhile."

Nevertheless, I did get my first chance to see my cock fully erect. I think I wished for a little too much. This thing was ridiculous.

The next day we're back at Student Center. As I walk down the hall I could see Jill talking to our friends, in the distance, having a good laugh. As I got closer I could swear the girls were looking right at my crotch. Oh well, fair is fair. After all I've ogled their bodies plenty of times.

And so ends my first fantasy. I hope you enjoyed it as much as I did. Or should I say, would have.

Look for the next chapter, coming soon.