Regrets and Fantasies Ch. 02

Chapter Two August 26, 1972

Michael and I were best of friends since second grade. We did everything together except, of course, intimate relations. Michael was pretty good looking not a knock out but he had something the girls liked. He always had a girlfriend and it seems he often had a couple at the same time.

Being his friend had it's benefits. We were always among the popular groups and I met a lot of girls. Unfortunately the girls always put me in the friend zone.

The only times I ever "got lucky" was when one of Michael's ex girlfriend's needed comforting or the surprisingly frequent "mercy fuck". In fact, I had developed the mercy fuck into something of an art form.

Which brings me to my latest regret / fantasy story.

I met Judy towards the end of the last semester. Her roommate was one of Michael's latest girlfriends. Judy's room had become the hangout in their dorm. She was a pretty wild girl. She did a lot of drugs and not just the typical marijuana and occasional psychedelic that were the norm at thath time. Her drug of choice was methaqualone (Qualudes) but when she couldn't get Qualudes she do anything she could get. Seconal, Morphine even Heroin. Although she only snorted it.

Judy was an extremely good looking girl. Classic hippy, long hair, no makeup, baggy clothes that looked like they came from the Salvation Army. For most of that semester I had no idea what her body looked like. Then one day I dropped in and she was wearing one of my favorite hippy girl outfits. Torn, hip-hugger, bell bottom jeans and a men's white sleeveless T-shirt - maybe one size too small. Wow! I took one look and I could feel my dick getting hard. And she made it clear that she noticed it. The shirt left little to the imagination. She had just absolutely fabulous breasts. Fairly large torpedoes with just enough droop to make them bounce. Her areola appeared a little puffy and soft nipples on top. I should also mention that she had a great body as well, but the truth is I was fixated on her tits.

The semester ended and we all went back to our home towns. Michael and I drove out to see her a couple of times. I was thinking that Michael had set his sites on her. He had that look in his eyes.

During the summer Michael worked at the local pharmacy. The man who owned the store loved Michael and wanted him become a pharmacist and work at his store. He had so much trust in Michael that he gave him the keys to the store so that he could assemble the Sunday newspapers. In the 70s there were four major Sunday papers. Over the last few Sundays of the summer I would help Michael with the papers in exchange for free reign of the store. Michael had been stealing stuff from the store for years. By time I was ready to go back to school I had amassed a pirates treasure of useful things. Six cartons of Kool cigarettes. A dozen cans of Arrid Extra Dry. A couple of boxes of Twizzler's licorice. Shaving cream, razors, clearasil and just about anything else you could think of - except - drugs. But then with Judy in mind I started loading up on pills as well. I'm pretty sure no one ever suspected anything was missing. I learned a lot about drugs in a couple of weeks. Methaqualone came in three different strengths and was made by three different companies. Two pills from each of the nine in total for three weeks got me 54 Qualudes. I did the same with all the other drugs I knew the names of. Then on the last Sunday, Michael unlocked the high powered stuff. He assured me that they had no controls of any kind. I took three morphine pills and four percadan. Then he showed me the cocaine. I wasn't completely unfamiliar with cocaine. I had done it several times. I also knew enough that whatever I had used had been heavily diluted. This was pure, pharmaceutical cocaine. I filled a small pill bottle about halfway. In retrospect I would guess it was about 8 or 9 grams. Michael had a family emergency and was going to take the bus a week late. I had my very cool Volkswagen Bug Convertible so I had to drive. It was about a four hour drive from Sharon, Mass to UVM. I had already done it several times. A day before I left Judy called me to ask me if I could give her a ride.

It was a warm, late summer night. Not a cloud in the sky. I picked up Judy at her house in Newton. She had one fairly small duffel bag and a back pack. She was wearing an Army shirt rolled up at the waist and the sleeves. To finish the look she had loose fitting denim shorts roughly cut about halfway between her knees and her waist. Nothing very provocative, at least I didn't think so.

It was about six o'clock when we left. Judy wanted me to put the top down but I said it was gonna cool down and besides doing the top on one of those Beatles was a pain in the ass.

For most of the first hour we talked about how we spent the summer. Not really very interesting. As we got to the New Hampshire border Judy said, "can't you put the top down. I'm broiling here."

"I was thinking of stopping soon for a burger. Maybe I'll take it down then."

"Oh shit, I'm dying." She said and unbuttoned her shirt. I was thinking maybe she had nothing on underneath.

It wasn't more than a few minutes later that she took the shirt off entirely. There was that sleeveless T-shirt underneath. I was trying get a good look and keep the car on the road at the same time.

Now, I was twenty years old at the time. And most normal twenty year old kids become aroused very easily. And just the thought that those tits were within sight caused my pants to start bulging.

It wasn't like she didn't notice. Judy enjoyed being provocative and at this moment she was provoking my libido.

"You're really holding onto that shifter pretty tight," she said, "Did you see anyone over the summer?"

"You mean like a girl?" I asked

"Yeah, did you get any?"

"Um, yeah. A little." I replied without a lot of confidence. I was hoping Judy had a little real interest in me and this wasn't another mercy fuck. On the other hand, any fuck would be OK right now. I actually had a pretty hot thing going for most of June.

She chuckled and said, "I'm sure you did. What was she like?"

I wasn't sure how to play this. I decided to go for the mercy and then go from there. "Well, she was a friend from high school. Nothing special."

"OK, well you know I think I know what you need. I can see the bulge in your pants."

I tried to cover it up and said, "No that's just the way my pants buckle."

"Come on, you know you'd love to get laid right now. Wouldn't you?"

"Ah, yeah I guess I would. Who wouldn't?" I said a little sheepishly.

"I can help you, Jared. We'll be at the dorm in another hour or so."

At that point I was feeling like I wanted this to be something better than sympathy or good will. "So is this a mercy fuck? You're gonna take care of the poor undersexed guy. I don't have a super hot sex life but I get my share."

"Oh really? I don't think so."

"Yup, just a fucking mercy fuck!"

Suddenly she seemed pissed, "You know I want to fuck you and your acting like it's something weird. Let's just forget about it."

And that was it. It was deadly quiet in the car for a half an hour or so. Then we were back to small talk for the rest of the drive.

Ok. That's what really happened. I've regretted it for years. But now we start where my fantasy takes over. We'll go back a little way.

I wasn't sure how to play this. I decided to go for the mercy and then go from there. "Well, she was a friend from high school. Nothing special."

"OK, well you know I think I know what you need. I can see the bulge in your pants."

"Oh, that's a little embarrassing but you know you really got me pretty horny."

I think I surprised her a little but she came back with, "I've noticed it before. I know you'd love to fuck me."

"Very true but I have to say a couple of things first. You could be trying to seduce me out of pity or something else. Or maybe not. The truth is you really don't know as much about me as you think. So let me find a place to stop for a second. I want to show you something."

Looking for a place to stop on I-91 in Vermont is not very hard. I got off the next exit and found a deserted spot that looked good.

"I brought you a little present." And handed her two Qualudes.

"Are you shitting me. I didn't think you did this stuff." Her face was lit up.

"Well I guess there's lots of things you don't know about me."

"You had ME fooled."

Then I pulled out the vial with the coke. "And I've got something else for you."

"What's that?"

"That is 100% pharmaceutical cocaine." I took out a spoon and held up a spoonful of coke for her. She snorted it and I wiped the excess with my fingers and rubbed it into my gums. We both did two spoons each. I was feeling pretty good.

The time was right. I gave her a deep kiss. She reciprocated and we continued for ten minutes or so without breathing.

Then she reached over and grabbed my cock over my pants.

"Now it's hard." I said teasingly.

I reached under her T-shirt and grabbed her right tit. It was a handful and then some.

The Qualude was starting to kick in. I decided to go for more. Now I understand why her shorts were so loose. And no underwear. I reached for her pussy just to see how wet she was - pretty wet. I started right into working her clit.

Judy unzipped my pants and pulled out my dick.

"Whoa, pretty big, Jared."

"That's what they tell me."

She bent over and put my dick in her mouth. She started sucking it pretty slowly. It seemed as though I was getting her pretty hot with my fingers.

Then abruptly I said, "let's do some more coke."

We did more and I got out of the car.

"What are you doing?"

"You wanted the top down."

I threw it back as fast as I could. Then I told her to get out. I took off my pants and sat on the passenger seat with my cock standing up like a flag pole.

"Get over here and sit on this but go slow."

As wet as her pussy was it was still really tight. She moved her ass back and forth and eventually took most of my cock in her cunt.

"Oh god, your cock feels so good." Grasping for air.

While she was riding my cock I was grabbing her amazing tits. Her nipples hardened quickly and got really big. As I rubbed her nipples she told me that her nipples are very sensitive and it was getting her really hot. Then, while keeping my right hand on her right nipple I used my left hand to massage her clitoris. At this point we were really going at it under the stars. The whole thing, the open car, the drugs, the beautiful sky, the full moon and great sex was really working. I was getting closer and closer but I wanted to hold off so we could come together.

She was pumping really hard and I was working her clit and nipple and I could feel her starting to tense up.

"Jared, I'm gonna cum. I can feel it coming."

"Yeah Baby, do it."

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

"I am too."

And we came. I grabbed her around the waist and just held her.

"That was fucking amazing, Jared. How did you get so good?"

"I guess I was just lucky. It was my first time."

"You asshole. You fuck like you've had lessons from a pro. At least a lot of experience."

"Ok I'll tell the truth. Being best friends with Michael means I have a lot of time when he's busy. Sometime's there's another girl there and when Michael goes off with whoever they get kinda horny. It's pretty easy to take advantage of the situation."

"There's a lot of horny girls around."

"I think you met Laurel Lesser."

"Yea, I remember her. Kind of a dog."

"Oh Judy, be cool. She may not be so great looking but she can really fuck. We were at Carole Goodman's house one time and Michael and Carole went up to her room to get busy. Well as soon as we heard the door shut Laurel threw me onto the floor, pulled out my cock and started sucking it. And really hard. Then she took off her pants and just jumped on my cock. In about two minutes she was coming. I didn't have time to catch up. She got on all fours and told me to fuck her. I'll tell you there aren't a lot of girls who aren't really tight when I fuck them but not Laurel. She was soaking wet and pretty loose. After a minute or so she reached back, pulled my dick out and put it in her ass. Now she was tight. That was my first time doing anal and it was great. It didn't take long for me to cum and Laurel too. She was screaming and yelling. I expected Michael to come down to check it out. Anyhow, she got up, put her pants back on and was about to leave when I spotted this big wet spot on the floor. She said she ejaculates when she cums. Her gynecologist told her it's unusual but does happen."

I could tell, for once I was getting Judy horny. She grabbed my legs and pulled me right out of the car onto the grass. By now she was completely naked. Her figure, lit by a full moon in an open field in northern Vermont was breathtaking. But she didn't give me much time to savor her beauty. She started jerking my cock fast enough to rip the skin off. Once again she straddled my dick and started humping. I was about to cum when she lifted her self up and slowly lowered her asshole onto my penis.

"That story made my so horny and I've always wanted to try this." She said as she slowly engulfed my dick."

It took her a few minutes to feel comfortable with a dick in her ass but when she did she started working it like a dog with a bone. Once again we came simultaneously except I stopped cumming after twenty or thirty seconds. She just kept going and going.

Finally she was able to gain some composure. "Holy Fuck!! I've never been fucked like this before."

"Don't tell anybody. It's my little secret. I mean it."

And it seems as though she didn't because after she left school (about two weeks later) I had no luck with the chubby blonde that lived on her floor.

Look for my next chapter coming soon.