"Best Friends" a Sad Story

My Friend Jessie and I have known each other since High School. I would always see her in school and kind of had a crush on her, but didn't know her much other then that.

I first officially met Jessie one night while I was hanging out front of another friend's house.

Jessie and her boyfriend drove up and parked and started talking with the group of us. The light in the tiny little pick-up truck that they were in illuminated the cab and I saw her boyfriend. As soon as I saw him, I mistook him for a guy I absolutely loathed named Curtis.

I wanted to just beat the ever loving hell out of him right then and there. Once my eyes focused however, I realized that it was not Curtis after all, it was in fact a guy named Dave that I also knew from school.

I was very shocked and surprised to see that Dave was dating Jessie, because, at the time, he was a scrawny kid that nearly everyone picked on. He was in many of the same classes as me, so I liked him and considered him a buddy.

Their relationship to me was like the head cheerleader dating the biggest nerd on campus. Only, Jessie was the kind of girl who hated cheerleaders, and Dave wasn't very much a nerd.

Jessie and I began to hang out alot, and rumors even started swirling that her and I were dating, which only made me feel better. Some of the guys I knew from school would often come up to me and give me "Props", but I didn't have the heart to tell them that Jessie and I weren't really dating.

We actually should have been dating, because I hung out with her a whole lot more then her and Dave did.

At the time, Jessie was one of the best looking girls that I had ever seen in person. She was tall and had a thin athletic body. Her tits were on the medium side, maybe about the size of two small melons. Jessie's dressing style was kind of grunge'e. She'd wear tight shirts, but loosely fitting pants. Her hair was unique, but it only made her look even better. Her bangs were pulled tightly to one side of her head, and the hair on the back of her head was styled wildly backward in a series of spikes. In a way, I liked to compare Jessie's looks to the Actress Jessica Biel.

Jessie had one of the most beautiful faces. It was almost angelic. Her face resembled a porcelain doll's face, and she had a really nice set of cat eyes. Kind of like the singer Taylor Swift.

Jessie was a few grades behind me in high school, but once we had both graduated, her and I hung out more and more. I really loved Jessie but could never bring myself to ask her to do anything sexually. Mainly in part, because I liked and respected her boyfriend Dave. Most other guys would have probably overlooked that aspect, but I didn't.

Sometimes, Jessie and I would just drive around for hours and hours together, and we'd covered fifty to sixty miles in a night, just driving around talking and listening to the radio. I even got so comfortable with her that I'd often reach over and massage her neck as she drove.

One Christmas,I had just gotten a new VHS-C video camera, and I carried it nearly everywhere. One day, not long after I gotten the camera, Jessie came over to pick me up so we could grab an early lunch before I had to go into my second shift job later on in the day. Her and I went to a local McDonald's where we ordered some sandwiches and french fries, and the two of us sat in her car in the parking lot, over looking the lake nearby.

I had pulled out my camera and kind of jokingly began filming her with it. She'd get angry because she didn't want anyone to see her eating but I continued filming her. Then, Jessie told me that when we got back to my house, that she would "Do something." for the camera.

My adrenaline began pumping, and I was anticipating what she was going to do. After finishing our food, we headed back to my house. I began to get so erect at the thoughts of what was going to happen, that I could barely contain myself.

As Jessie and I reached the back door to my house, I reached for the handle and it wouldn't turn. I didn't have a key at the time, so I tried using a little garden trowel to jimmy the door open to to no avail. I tried anything and everything to get the door open, even trying the old credit card trick, but nothing would work.

Sadly, I did not get the door open, and I didn't have any more time to work on it before I had to head into work. A few times after that, I tried to get Jessie to fool around for the camera, but she always seemed way too nervous to do anything.

Sometimes, Jessie and I would sit in my attic computer room and just search various porn sites, and she enjoyed every minute of it. Even commenting on what turned her on and off.

Most of the time when Jessie and I were hanging out, our topics would turn to sexual topics. I remember one day her and I talking about clit piercings and how I had heard that it enhances the orgasmic pleasure for a woman. Jessie had never heard that before and her reaction was.

"Oh, I'm getting it done."

Jessie and I hung out for nearly two or three years before she and her family decided to move back down to the south where they were originally from.

I could really kick myself for this, but. Jessie and her slightly younger Sister visited me once after she had moved and when she came to my house, I was so upset at her for moving that I didn't even feel like talking to her. If I recall, I think I might have even told her that I was sick and couldn't go anywhere with her. As she was getting ready to leave, she reached out to hug me and I barely embraced her. I even felt her kiss the side of my neck, and I almost broke into tears.

That was the last time I had seen her or even heard from her for the next four years.

Since Jessie and I had many mutual friends, the two of us had gotten back in touch with each other. by then, I had also moved out of state.

Jessie and I would chat on the internet and when we didn't, we'd always ask our mutual friends about each other's wellness. To my dismay, I had found out that Jessie had gotten married and had a baby son.

One night, around the same year, Jessie and I were talking to each other online and the topic turned to sexual topics. Jessie was typing through our chat box and told me something that I will never, ever forget.

"I'd fuck you in a heart beat."

Jessie, to this day, is the only girl who freely admitted that she wanted to fuck me.

Not long after that, I was checking my E-mail one night and I saw Jessie's E-mail address and in the topic bar were the words. "Hot pics, open alone."

When I opened the E-mail, there were two pictures of Jessie kneeling on a bed which were taken from behind, a picture of her with jeans, but no shirt on, another picture of her giving her husband a blowjob, and a close up picture of her husband's cock sliding into Jessie's plump bald Pussy.

Seeing these pictures both turned me on and disappointed me for two reasons. The first reason was that it was not me in the pictures with her. The second reason was because Jessie was no longer the thin, athletic beauty that she was just four or five years before. At the time the pictures were taken, Jessie was nearly fifty pounds heavier and was kind of unattractive.

No matter what, I still wanted to fuck her. The more and more that I talked to her online and on the phone, the more I found out about her. I learned that her and her husband had become "Swingers". They wouldn't just swap couples like real swingers would, but her husband would often let other guys fuck Jessie. I was turned on by this, but I also felt bad because I didn't want to see Jessie getting used like that.

Again, Jessie and I had lost touch with each other, and when we'd hear from each other it would be further between the last call.

When we finally got back in touch with each other again it was 2010. We would call each other nearly every day or if not, maybe a couple of times a week. In late spring 2010, Jessie told me that she wanted me to come and visit her in the south where she was still living. I wanted no more then to do that, but knew I couldn't afford a plane ticket or even a train ticket to go.

Then, Jessie told me that her husband and her would come and pick me up. On the weekend they were supposed to show up, I awaited their arrival, no one ever showed. Jessie called me a few days later and told me that they couldn't make it up that weekend, but they'd come up the next.

Another week later, I had stayed up all night awaiting their arrival. Jessie and I had talked the night before and they said that they'd be up.

I lay on my bed looking out the window when suddenly I see a light blue Chrysler Town & Country slowing down when they reached my house and in the passenger seat was none other then Jessie. I quickly ran outside to meet them and when Jessie emerged from the passenger door, I fell in love with her all over again.

Jessie had lost a good thirty pounds. She wasn't quite as thin as she was when I first met her, but she was looking really good to me.

Jessie introduced me to her husband for the first time, then she introduced me to her son. They had breakfast with my Dad and I before we began packing my luggage into their van for my first trip below the Mason Dixon line.

The ride to the south took a grueling eleven hours. I hadn't slept the entire night before, but since Jessie and her husband were taking turns driving, I stayed awake to make sure that they stayed awake.

My plan was to stay with Jessie and her family for an undetermined amount of time, and possibly get a job somewhere in the south and eventually move in with them.

The first full night there, Jessie, her husband and I sat around bullshitting in their living room and Jessie wanted to get ready for bed. She turned to me and says.

"You wouldn't be offended if I get dressed in my night clothes do you?"

I didn't know what "her night clothes" were, but I didn't care one way or another. Jessie runs away into the bathroom and emerges wearing a tight pink top and a pair of matching pink shorts. She looked really good. She sat on her husband's lap and the two of them began talking. Then, I heard her husband say the words.

"I wanna see how furry your goods are."

He turned Jessie toward me and slowly pulls the front of her pajama shorts down revealing her Pussy with a few days worth of hair coming through.

Jessie laughed, but I guess didn't feel comfortable enough to have let me seen her like that, so she quickly pulled her husbands hand away.

I was happy to have seen the little bit that I had just seen, so I didn't care.

The next night as the three of us turned in for the night, I lay on the floor in the living room. Jessie and her husband slept in the bedroom, and their son had a folding couch bed.

I was nearly asleep when I heard Jessie moaning softly and the springs of their bed squeaking. I kind of smiled at what I was hearing, but deep within I was also saddened, because they didn't invite me in, and it wasn't me fucking her.

A few nights later, Jessie, her husband and I were sitting in the dining room having some drinks when Jessie grabbed one of my still cameras and began fooling around with it. She took random pictures of me, then of her husband, before her husband grabbed the camera from her. He begins telling her what to do.

Jessie pulls her now very large tits from her shirt and her husband snaps pictures of them. Jessie smiles and assumes various positions while her husband continues taking pictures of her.

Jessie then grabs my hands and cups them around her tits and her husband snaps a few more pictures. After that, Jessie and her husband talk about something while I listened but not making out anything of what they said.

Then, Jessie asks me if I would watch their son while her and her husband make a run to the adult store around the corner from where they lived.

About twenty minutes later, Jessie and her husband return and sit and finish their drinks at the table. Then Jessie reveals the toys that she bought from the store.

The one toy was a huge purple dildo which I quickly dubbed "Barney". The other was a vibrator that had a curled plastic tip. After finishing their drinks, Jessie turns to me and says.

Well, I'm going to bed with my toys now." and her and her husband disappear into the bedroom.

I was not tired, and I wasn't going to sleep on their count so I sat up watching TV. I don't recall what I was watching, but I began laughing. Next thing you know, I hear Jessie's husband's voice say.

"Hey, Mike, bring your camera over here buddy."

I stood up and walked around the corner to their bedroom to see laying on her back spread eagle and her husband is shoving the curled vibrator in and out of her Pussy.

I turned the camera on and began snapping pictures of what I was seeing. After a couple of minutes, Jessie's husband snatches the camera from me and points between Jessie's legs. I kneel and begin licking and sucking Jessie's Pussy.

Jessie reaches down with her right hand and begins rubbing and squeezing my forearm as I was eating her out. I fingered her quickly and then slowly, and continue to lick her.

Then, I don't remember who handed it to me, but I found myself holding "Barney" in my hands. I quickly plunge it deep into Jessie's Pussy.

I continue pushing and pulling the large purple dildo from her Pussy and then I begin twisting it in a corkscrew motion before going back to eating her out again.

I was then ordered to lay on the bed. Jessie kneeled on the bed and began stroking my erect cock. Her husband worked his way in behind her and began fucking her from behind. I soon became very nervous and embarrassed because the headboard started banging loudly against the wall, and I was worried the neighbors in the apartment room next door would hear us and complain.

Suddenly, I felt a great urge of pleasure and looked down just in time to see Jessie pulling my cock from her mouth and licking quickly around the head.

Jessie continued stroking my cock and I asked her to suck it again.

"Hmm?" Jessie asked.

"Can you suck it again?" I asked her once again.

Now, I don't know what she meant by this but she said something along the lines of.

"I got it right where I like it."

Jessie just kept stroking my cock, but I wasn't getting any closer to cumming.

I'm not sure how much time progressed, but then, Jessie's husband handed me a condom.

When I saw the condom, I became both even more aroused, yet even more nervous.

I remember saying something along the lines of.

"I don't wanna do all that." and Jessie's husband's reply was.

"Well, she wants to."

Jessie looked up at and stopped stroking my cock and in an angered, yet sarcastic tone she said.

"You take insanely long."

Before I knew it, the three of us were sitting back at the kitchen table, each of us completely naked and each of us smoking a cigarette, and drinking our alcohol. I kind of just figured we were taking a break, but I found out minutes later, it was all over.

Jessie and her husband went back to bed and I laid in my spot on the floor and jerked myself off.

That was my first time ever doing anything like that and it was the best and worse night of my life. I had gotten a hand job from a stripper the day after Christmas a few years before, and I was closer to cumming with the stripper then I was with Jessie.

I don't know if it was because I was more drunk then I had ever been in my life, or if it was nervousness for it being my first time ever going that far with a woman. It might have even been the fact that her husband was in on the whole thing and I might have been turned off a little because of that.

I trained myself to last a long time, because I heard that women love a man who can last long, and I can last probably an hour or more. This has become more of a curse then a benefit for me.

Now, those of you reading my ramblings right now are probably thinking. "We want to see the pictures."

Well, here is the story about that.

A few days after our encounter, I accompanied Jessie's parents on an over night trip out into the country side to visit some of their family. As I lay in the guest room at their relatives house I began jerking off. I grabbed my camera and turned it on so I could look at the pictures that I and Jessie's husband took. They were no longer there.

I asked Jessie the next day what happened to the pictures. She had told me that she deleted them.

When I asked her why, her reply was simply.

"I don't know."

I will never forgive her for deleting the pictures, because right now, I know how everything happened that night, but I can't quite remember anything else, because I was drunk.

I stayed in the south for three weeks before taking a Greyhound bus home. About a month after being back home, Jessie calls me, and she is drunk.

She tells me that she wants me to eat her pussy again because I was the best to ever have done that to her. And, she told me how she thinks of it often.

About a year after my visit. Jessie separated from her husband and calls me one night. I could tell she was drunk again. She says something like.

"Your gonna kill me."

When I asked her why she says.

"Someone got me to try coke." As in cocaine.

I laid into her about how much I love her and don't want to see her getting into anything else. I already knew she smoked weed and drank alot, which I didn't like either, but once she told me that she had tried cocaine I wanted to go back down to the south and beat the shit out of the motherfucker who got her to do that.

Jessie continued drinking heavily and smoking weed, and became sexually involved with a guy who looked like a homeless meth addict. I wrote a letter to Jessie telling her how much I cared for her after that, and she calls me crying, telling me how much she loves me, and how she'd love to marry me and have kids with me.

I still love Jessie, but I am no longer in Love with her.

Even now,when I think about her sexually, I don't think about just making love to her. I fantasize about treating her like a whore.

I've actually told Jessie what I want to do to her, and she tells me that she'd be interested, but I don't think she'd be really interested.

One of the things that I would love to do to her is have Jessie carry a sign that reads; "I AM A WHORE." and I'd make her walk along the shoulder of a busy highway for a couple of minutes while I take pictures and video from the safety of a car.

Another thing that I want to do is either fuck her or get a blowjob from her while sitting in a van. Then, I will cum all over her face. Then, I will set up a hidden camera on Jessie and have her walk into a fast food establishment with the cum on her face and record the reactions of the people behind the counter.