Jackie Loose In Love

I first met Jackie when she came to visit her brother (Sam) who lived in my dorm back in college. Jackie was not a beautiful girl from the neck up but from the neck down she was pure sex.

When she first arrived it was winter and she was wearing a thick coat. We were a house of six testosterone driven guys who would fuck pretty much anyone or anything but none of us were particularly excited to meet Jackie.

She was staying for a week in our house and it didn't take us long to realise that she was a great laugh - one of the boys. There was no interest in trying it on with her so we treated her like one of the guys and she seemed fine with that.

We all got very drunk that night and Jackie was keeping up with the shots. Towards the end of the night, at about 2am she disappeared to get changed into her bed clothes.

10 minutes later she walked back into the room and you could almost hear the erections going up as she did. It turns out that although Jackie had an unfortunate face, her body was something to die for. Long slim legs, sexy curve at the hips, and huge tits were threatening to burst out of the skimpy nightie she was wearing. We could clearly see her nipples straining against the fabric and they were drawing the intense stares from every one in the room (even Sam which was strange).

The atmosphere after she came back down was completely changed. Gone was the room full or uninterested guys, replaced by a room full of guys that couldn't have been more interested in her if they had tried.

Jackie for her part seemed to love the attention and flirted away with all of us.

The night went on and on and Jackie stayed up but we started to drop off one by one. First Sam, then Jack, and then me, which left Chris and Jackie alone together. I hadn't been in bed for more than 10 minutes before I heard the bed banging against my wall from Chris' room.

Chris didn't last long, I think he came quickly and then rolled off leaving Jackie unsatisfied. After another 10 minutes I heard someone coming downstairs and heard Jack's voice from in the hallway outside chatting to Jackie. I was just about to drop off to sleep a few minutes later when I heard the same rhythmic banging but this time from the room above me - Jack's room. He lasted a bit longer (still less than five minutes though) and then there was silence.

The next day everyone was a bit sheepish apart from Jackie who was acting the same as before. Sam was clearly pissed off with Chris and Jack and spent the whole morning complaining to me about it. This was a major problem for me, Sam and I was very close friends and by complaining about them fucking Jackie he was also making clear that I couldn't get involved.

The next week was a blur of bad sleep. Every night would end with the same pattern of Jackie fucking Chris and then Jack. There was an intense chemistry between Jackie and I which was made worse by Sam forbidding me from doing anything. I satisfied myself by just jerking off to mental images of her body, which was made a lot easier by the revealing clothes that she wore all the time.

Jackie went home again but then returned about three months later. We had a new housemate called Craig and Jackie gave him priority in the routine. She went from Craig's bed, to Chris' bed before finally ending in Jack's.

We assumed that Jackie was staying for a week like she did before but a week came and went and she showed no sign of leaving. By the end of the second week she was still with us and Jack had lost interest. Craig and Chris continued to fuck her every night until finally, after about four weeks, Craig lost interest too.

This meant that Chris had her all to himself and he seemed very relieved. Chris was not exactly blessed with good looks and had never had a serious girlfriend. We all tried desperately to warn him that Jackie, as fun and sexy as she was, was definitely not girlfriend material.

After week six she let it drop in conversation that she had dropped out of her college course and couldn't afford her dorm rent so they had kicked her out. Chris jumped at this like a dog for a treat and said she could move in with him permanently, which she did.

Jackie living with us full time changed the dynamic a lot and Sam, Craig and Jack started to get seriously annoyed with the Chris/Jackie combo. She didn't help with cooking or cleaning and never left the house.

Personally I didn't mind at all. She was good fun and she and I really clicked, it sounds shallow as hell but if it wasn't for her face I think we would have got together properly and been really happy (apart from her whoring ways).

Eventually the tensions got too much and Jack and Sam told Chris to leave. This was made more difficult by the fact that Chris had basically dropped out of attending college so that he could spend all his time with Jackie.

They moved out to a shit apartment in a shitty neighbourhood and Chris started working as an Uber driver. Jackie's reaction to their lack of money or prospects was, for some reason, to start pumping out babies. She got pregnant with their first within a few months of leaving our dorm.

I stayed in touch and visited occasionally. Jackie was one of the sexiest pregnant women I have ever seen and there was a lot of weird flirting between us. Jackie gave birth to her son and then got pregnant again almost immediately. They needed a bigger house so they moved away out of state.

On the night before they left, we organised a night out at a bar to say goodbye in style. Chris stayed in and babysat and so Jackie was back to her wild ways. Her tits were full of milk and were almost exploding out of her top that night. She and I hung out all night and when it was time to go it was pretty emotional. I was also horny as hell. I walked her back to their house and there were a few moments where something almost happened between us but every time we were interrupted. Eventually we said goodbye and had a long, heartfelt hug.

The town they moved to was about a six hour drive away and in the middle of nowhere so we kind of lost contact. Every now and then we would message each other and speak on the phone to catch up but that was all.

For my part I got a long term girlfriend and we moved in together. I kept up with Jackie's life via social media and saw that she had another three kids, making it five in total.

Eventually we lost touch completely until one night, almost 16 years after she had moved away, she messaged me out of the blue to say that she was coming to Detroit and she wanted to meet up. All the old feelings rushed back as we arranged to meet.

I was living with my new girlfriend, Emma, and I asked her if it was ok if Jackie stayed over for a few days. Emma obviously said no but I showed her some (purposefully unflattering) pictures of Jackie and Emma laughed when she saw what Jackie looked like. She said she was happy for Jackie to stay the night and didn't feel that she was any threat at all. What is more, Emma, said that she would go and stay at her mom's house for the weekend so that we could catch up properly. I felt guilty but also lust will make people do horrible things, and the lust that I felt for Jackie was almost all consuming.

Friday came and I went to meet Jackie at the train station. When she stepped off the train, I was a bit surprising to see how badly she had aged, we were only 40 but she looked like a worn out old farmers wife.

Still it was good to see her and we immediately felt comfortable with each other. We got back to my place and I made her dinner and time flew as we caught up on each others lives. We drank a lot but nothing happened that night, I was feeling the historic lust for her but had no feeling of attraction whatsoever - an odd combination!

We hung out the next day and she updated me more on her life. She was still with Chris but he was a cuckold husband and so she was free to sleep with anyone she liked. I asked her if she still loved him and she seemed taken aback by the question, her answer when it eventually came was not convincing.

That night I told her I wanted to take her out for dinner and I booked a table at the nicest restaurant around us. I was feeling sad about her life and really wanted to treat her to some luxury which was obviously lacking in her life. When I told her about the reservation she was so excited that she threw her arms around me with a huge hug.

When we got home at about 6pm she had a shower and then went straight to her room and told me she wouldn't be out for at least an hour because she wanted to get dressed up. I threw on a nice shirt and some trousers but didn't make too much effort so sat down to watch the game on TV.

An hour passed and Jackie hadn't appeared and I started to worry that we would miss our reservation. I shouted for her to hurry up and she said she wouldn't be much longer. She was half an hour longer and I was just starting to get seriously annoyed when her bedroom door opened and out walked the sexiest image I have ever seen in my life. It is hard to describe but I will try, she wore a red dress which was tight and short (I said she looked sexy not classy) with a plunging neckline that revealed her famous tits. They had sagged quite far but they were still magnificent, she was also not wearing a bra which meant her two prominent nipples were making themselves known. She had done her hair and make up too and although she didn't look beautiful, I had come to love her face and so seeing her now I felt like I was in love with her.

She started to get embarrassed as I stood staring and not speaking and when I finally recovered all I could say was 'wow'.

The Uber picked us up and took us to the restaurant. As the waiter showed us to our table every single guy in the room turned to watch as Jackie followed to the table. I could tell they were trying to work out what the relationship was between us and I imagine that they settled on 'dolled up hooker with wealthy white guy'.

We had a nice night and Jackie was really enjoying herself but I was feeling uncontrollable surges of lust for her. The conversation drifted to the subject of she and I and we both commented on the fact that we had never slept together and how weird that was. She told me that there had been many times that she had wanted to but didn't want to ruin one of the few good friendships she had. I told her that there had been many times that I had wanted to but had been warned off by her brother Sam. She found that hilarious because, as she pointed out, she had slept with every single one of Sam's friends multiple times.

By the time we got in the Uber to go home the sexual tension in the air was overwhelming. My cock was aching from being hard all night and I was aware of a mess of precum from being endlessly turned on.

We got out of the taxi, walked through the front door and stood awkwardly for a bit. Neither of us knew what to do so I asked if she wanted a drink and she said to make her a vodka and coke.

We sat together on the sofa and she talked away while I devoured her body with my eyes. Her legs were still long and slim, her hips had the sexiest curve to them which was accentuated by the red dress, and those tits... oh those tits. I was having to consciously restrain myself from burying my head in them. She was pretty drunk by now and slurring her words and I wasn't feeling much better but it was adding to sexual energy.

I snapped out of it when I realised that she had just asked me a question. I admitted I hadn't heard her and she repeated "Why do you think it was that we never slept together?" I couldn't think of anything to reply with and sat there in silence until she followed up with "You could of had me you know, anytime, anywhere - I was always yours."

I stared at her for a moment and then all resistance disappeared. I kissed her long and hard and she kissed back with equal passion. She hitched up her short dress and I pull off my pants quickly and sank my cock into her pussy. Or at least that's what I thought I had done, I couldn't feel anything at all. I put my hand between her legs and felt for her opening which was soaking wet. I grabbed my cock again and thrust inside her but again I couldn't feel anything. I looked awkwardly at Jackie who gave a slightly embarrassed apologetic look and said "You won't get much pleasure in there I'm afraid, best to try the other hole" and with that she turned around and bent over, grabbed my cock and then shoved into her asshole.

In my drunken state this was a huge turn on and I fucked her ass for a long time while she rubbed her clit. After a while I realised that I hadn't actually managed to enjoy her tits yet and, not knowing if this was a one off fuck or not I didn't want to miss my opportunity.

I pulled out of her and told her to take her dress off which she did. It was not a sexy strip - we were both too drunk for that - it was frantic undressing until she turned around to reveal the tits that had been the object of my fantasies for so many years.

They were as amazing as I had always thought. Huge, full tits which sagged all the way down to her belly button. I pushed her back onto the sofa and proceeded to suck on those nipples for all I was worth. She rubbed her clit again and came for the first time. I grabbed my cock and managed to shove it back in her asshole while I was sucking on her tits and I was in heaven.

I didn't last more than a few minutes before I came hard inside her and we fell on top of each other in a drunken heap.

We went to bed and had sex again in the night and then again in the morning. Each time it was in her ass because her pussy was too loose. The next night we just had dinner and then went straight to bed. I wanted to ask about her pussy but she beat me too it, she told me that her biggest turn on was being fisted and stretched in her pussy and that over the years (together with multiple child births) things has had gotten a lot bigger down there.

It was a huge turn on for me in a slutty kind of way but it was also a source of huge frustration. I kept forgetting about it and would try and shove my cock in her only to feel nothing more than a warm, wet cave.

I fisted her that night and she wasn't kidding when she said she was into it. Two fists wasn't enough so she went to her suitcase and took out a huge dildo which she inserted with my fists.

I was happy though because her ass was still pretty tight. She had also learned a trick where she could contract her ass muscles in rhythm with me fucking her and it felt amazing - like her ass was sucking the cum out of me.

Anyway, the weekend ended and she went back home. I broke up with Emma shortly after (feeling guilty as hell) but Jackie refused to break up with Chris saying that her family was the most important thing to her.

Since that weekend we have met up six more times and each time has been crazier than the last. This has been going on for three years now and it makes it impossible for me to have a normal relationship but I can't possibly stop seeing Jackie, the sex is the most fulfilling thing I have ever experience - physically and emotionally.

So there you have it - my fucked up life.