Jillian's Magic

I was always a bit jealous of Chris growing up. He would have the hotter girlfriends. He was good looking but it was mostly due to the fact he was the quarterback of the football team. However, the hot cheerleaders and other girls he ended up fucking after the games didn’t realize I was the reason he was good. I was big and muscular, but I was on the line making blocks for him so he could throw all those touchdown passes and pose for the cheerleaders. I was the smarter one, yet he got a scholarship to college because I made him look good on the field. Nonetheless he did appreciate everything I did for him and we had been friends for a while…all the way up through college in fact. He knew I was a big part of his success.

When we graduated we went our separate ways for a few months but eventually found our way back to the same town coincidentally. It was a small town about 45 minutes away from where we grew up…closer to the big city where we both ended up working in different jobs.

While we grew up through high school and college Chris would always have the good-looking girlfriends. I had my share too but they always ended up going for him before they went for me. When we were at a party for example and we were standing together with a group of girls, a girl’s first inclination would always be to flirt with Chris first and I would get the leftovers. After a while it even got old for Chris. He had a few last fuck flings with hot women but then found Jillian and settled down.

You can understand why Chris settled down with Jillian of all people. There was something about this 5’10 long-legged brunette that would just light up the room when she walked in. She had a body you knew she worked out every day. I know you hear about girls like this all the time but Jillian was different. When she walked in a room every straight guy would stare at her regardless of whether his girlfriend or wife was in the room. It was inevitable this would happen. The fact Chris was able to land her as a wife was incredible in itself, but it also meant I would get to spend time with her as Chris and I remained friends. I was the best man at his wedding. Jillian became good friends with my girlfriend at the time, Ali. Ali was a short blond cutie, but nowhere near what Jillian was. Chris and Jillian got married in a nice ceremony and we all got drunk and had fun at the reception afterwards. No there was no monkey business on the wedding day like I know you are all hoping. Chris and Jillian went off on their honeymoon to Hawaii and Ali and I went back home.

Two weeks had passed when Chris and Jillian got back and settled into their new home, which her parents had paid for. Apparently Jillian’s father was some sort of rich investment banker who had cleaned up during the dot com boom of the late 90’s. In fact he didn’t even lose that much money when all those tech stocks started to bust. He had made enough money to live comfortably in 10 lifetimes. This meant Chris and Jillian could do whatever they wanted. If Chris wanted to work he could and if he didn’t he didn’t have to.

Ultimately Chris decided to become the town’s high school football coach. He wanted to work but didn’t want a real demanding job. He wanted something he could enjoy and that was football. I, on the other hand had to work my job as a banker which wasn’t all that bad but was very demanding on my time.

One of the first things Chris did when he came back was tell me about his honeymoon. He and Jillian had a blast in Hawaii and Chris couldn’t have been happier than he was at that moment. “You have no idea how great the sex was buddy” Chris said.

“I can pretty much imagine with a girl…I mean WIFE like yours. I wouldn’t expect anything less.” I replied honestly.

Chris then went into the details of their honeymoon. The ways she liked being kinky like tying him up and being sexually dominant in bed and then in the blink of an eye she could turn submissive to let him be in control. He went on to say how she got on top of him and rode his cock like she was a jockey in the Kentucky Derby. They had sex in the ocean, on the beach, on a park bench (she brought a long skirt with her for that one) and in bathrooms at dinner because they couldn’t get enough of each other.

I went home to my girlfriend and was really horny the entire ride there thinking about the lovely Jillian doing these dirty things Chris had mentioned. What I wouldn’t have given to be Chris at that moment. I thought it was kind of awkward for him to have told me about his experiences, but I sure didn’t mind.

My girlfriend Ali and I had been going out for a year and a half and things were starting to get pretty serious. I thought she was the one and would probably ask her to marry me in the next year or so. She was the kind of girl that took care of you in and out of bed and who I could picture spending the rest of my life with.

When I got home that night Ali was in the kitchen cooking something for dinner. She was stirring up something so I decided I would sneak behind and start stirring her juices inside. I snuck up behind her and kissed her neck while my hands roamed around her small, yet tight body. Ali was responding to it moaning gently as she grabbed my leg from behind and pulled me closer to her. I then tugged down on her jean skirt she was wearing, turned her around, lifted her up and sat her down on the counter.

I was hungry waiting for dinner and now that I knew it would be a while, I went right for her little pussy. I slid my finger in and then leaned down and began to flick my tongue on her clit. This drove Ali wild in addition to every other woman/girl I had ever been with. She loved it and I loved to go down. I kept at it for a good 10 minutes causing her to cum at least twice. I had perfected my technique over the years to send girls over the edge in a matter of about five minutes. I was getting way too horny at this point with Ali cumming and the thoughts still lingering in my head about Chris fucking Jillian on their honeymoon. I had to put my cock somewhere that moment. I had that feeling where I needed to be satisfied that moment.

I took my pants down and Ali began warming me up even more, although I was warmed up enough. I spread her legs apart even more and leaned in while she was still sitting on the counter and slid my engorged cock inside Ali’s tight pussy. “MMMMMMM” she belted immediately. “OH GOD YES…YESSS” I remember her saying while I did that. I started to quicken the pace a bit going faster nearly giving her a concussion as I slammed the back of her head into the cabinet with my thrust. It didn’t seem to faze her as she thrust her hips right back into me.

I then put my hand behind her head so she wouldn’t get knocked out and fucked her really hard. Her legs wrapped around me and I started in with the dirty talk I gave to so many people. “You like getting your tight pussy slammed with my cock. Doesn’t your pussy feel good around my cock? Did you like me sneaking behind you like that when I came home? I needed your pussy so bad” I said which got her really hot.

“OH FUCK YES…I LOVE YOUR COCK AND I LOVE WHEN IT SLAMS INTO ME LIKE THIS. DON’T STOP…KEEP FUCKING ME. I’M YOUR SLUT” Ali said starting to really get into it now.

Something strange happened as I continued to pound my meat inside my girlfriend. I closed my eyes for a few seconds and imagined I was fucking Jillian. She had been on my mind that entire time. Thinking about her long legs around me, thinking about her controlling me telling me to fuck her the way Ali was, just made me that much more horny and excited. I found myself fucking my cock into Ali as hard as I have in a while and she was getting off on it. Little did she know it wasn’t all her who was getting me off. Physically Ali was but mentally it was all Jillian. For as long as I can remember I have been turned on by mental images sometimes as much as someone’s physical presence.

I didn’t know how much longer I would last inside Ali. She was really squeezing my cock inside her tight hole as I drilled away. “OH MY GOD…OH MY GOD. FUCK ME!!” she screamed. She had cum about four times by that point and I had enough. I needed to blow my load and soon. She was squeezing me so hard with her tight pussy that I had to cum in her. Now keep in mind she was always against me cumming in her. She wasn’t on the pill and didn’t want to get pregnant until she was married. I understood that but the urge was too great and I had to do it. I had cum in her a few times before but never managed to slip one past the goalie so to speak.

I guess she could sense I was approaching climax and she tried to squirm away, but it was too late. I shot my huge load inside her. All I could think about was Jillian’s pussy squeezing my cock instead of Ali’s. It made me cum that much harder and made me shoot that much more cum inside Ali’s small body. I then collapsed on her and reality set in.

“You fucking asshole, why did you cum in me…you know I don’t like that” she said.

“You certainly seemed to like what I was doing before. You know I can’t help myself sometimes” I responded walking toward the table to put my pants back on. Luckily Ali didn’t get pregnant for both our sakes. I wanted to have kids very much but not until I got married. In fact I wanted a basketball team full of kids.

A year later Ali and I were engaged and still living in the same place. We set a wedding date to be the following Spring which was still about six months away. To celebrate our engagement and Chris and Jillian’s one year anniversary we went out to a fancy dinner with Chris and Jillian at this restaurant. Jillian picked up the check which ended up being over $500. We had some really great seafood dishes thrown in with a couple of bottles of expensive wine. Naturally the conversation turned to sex and Jillian asked us how much better “engaged sex” was than sex when you were just boyfriend/girlfriend. The conversation turned pretty graphic because we all had alcohol in us. Ali said how great our sex life was especially now that we were engaged. We were so uninhibited because we both knew each other’s bodies so well. Chris and Jillian agreed and than made a big announcement.

“Chris and I are trying to get pregnant” Jillian said. “I’ve wanted to have a baby and a family for as long as I can remember. It’s been a dream of mine” she added.

I had as much alcohol as the rest in me at the time and blurted out something crazy, “I bet baby-making sex is even better than engagement sex!” Everyone broke out laughing and Jillian just stared at me with a strange look sort of half nodding her head. She had this look of lust in her eyes like she wanted to take Chris back with her that very second and fuck his brains out. It was then I started remembering that day when Chris told me about the events from the honeymoon. For the past year I had thought of the story at least every other day and it was magnified even more when we got together with Chris and Jillian.

“I’m really happy for you guys” I said as I raised my wine glass to toast to their attempt at getting pregnant. “To Chris and Jillian…May you have many years of happiness and a huge family” I concluded.

“I’ll second that one” Jillian said as we all knocked glasses together. Dinner ended shortly after and we all hopped into the stretch limo paid for of course by Jillian. I fucked Ali really hard that night because I pictured yelling at Chris to “get me pregnant.” I came deep inside Ali who was on the pill.

Later that night when we were talking about Jillian and Chris trying to get pregnant she informed me she wanted to wait about five years after we got married to start having children. That disappointed me because I was ready to have a family right then and there, even before marriage. Well maybe that’s exaggerating a little bit, but I wanted kids in the near future right after marriage.

The rest of those six months leading up to our wedding Ali ordered me around and had a one track mind…get ready for our wedding. I offered to help but she wouldn’t let me go near anything. Everything had to be done the right way, which in this case was her way.

One day shortly after the conversation, she told me to go over to Chris and Jillian’s to pick up their wedding album because she wanted to study some kind of design of something. I wasn’t really paying attention but jumped at the chance of going over to see Jillian. I quickly gathered my things and headed in my car for the five minute drive over to their massive house.

When Jillian answered the door she greeted me with a big kiss on the cheek and a hug. She was always such a happy person but for some reason looked a little sad when she answered the door. I didn’t think anything of it and walked inside. She was wearing a tight pair of jeans which showed off her shapely legs and a low cut shirt so I could see her cleavage. I tried not to stare but I couldn’t help but notice how amazing she looked. She was like a movie star that you saw out on the street dressed normally. You know what I mean…what’s normal for a movie star is what everyone else pictures to be hot. That was what Jillian looked like at that moment.

As I walked in Jillian offered me something to drink while she went upstairs to get her album. I said I’d take whatever she had in the refrigerator. She came back with a beer and sat down with me while I drank it. “Where is Chris” I asked.

“He had to go to some football conference” she replied kind of frustrated.

“What’s wrong with that?” I asked curiously.

“Well, I know he can do whatever he wants but I just hate what he does. At first it wasn’t so bad but now all he talks about is football and what he’s doing with the team. I wish he’d just quit. It’s fucking high school for god’s sake. Can’t he get a real job like you?”

“Come on Jillian. You knew football was his life when you met him. Is that really what’s bothering you here? Seems like there is something else going on” I said. Jillian started to break down and cry. I couldn’t believe it and couldn’t imagine what was bothering this person I knew to be such a strong woman.

“It’s not just the football. It’s been almost six months and I still haven’t gotten pregnant. We were trying to conceive before that dinner we had with you guys. Chris called me before he went to the conference and told me the doctor said he didn’t produce enough sperm to impregnate me.” She really started to break down now. “I’m sorry I shouldn’t be putting all this on you” she said.

“It’s okay” I said as I went over to the couch to and put my arm around her and comfort her. “You two can adopt kids. There are plenty out there who need homes. I sort of know how you feel. Ali and I have been talking about starting a family after we get married and she wants to wait five years and even then she said she’s not sure if she wants to bear a child. I told her I don’t know if I would be able to do that. I want a family really bad like you do” I told her as I started rubbing her back.

“Really?” she said half surprisingly, half still upset. “Why wouldn’t she want to have kids with you soon…you two would make great parents and would have beautiful kids.”

“Thanks Jill, I think anything that comes out of your body and anything you do turns to gold. Things have a way of happening for a reason.”

“Oh thanks, but there is no way this will work out for the best. I know I can adopt kids but it’s always been my dream to carry a child and have at least one of my own.”

Jillian was in her weakest moment and I wasn’t quite sure how I should have gone about comforting her. I didn’t know what to say so I just continued to rub her back. She fell into my arms and continued to cry on my shoulder.

“I’m so sorry for putting all this on you…You’re being as sweet as anyone could” she said lifting her face up and giving me a kiss on the cheek. I don’t know why but I was getting turned on by Jillian. Even in a moment like this just feeling her body against mine sent blood rushing through my body. My heart was pumping a million miles an hour and at that moment I leaned in and gave her a kiss on the cheek. I thought that would be the end of it but she immediately leaned back into me and kissed my lips lightly.

“OH GOD!” I’m so sorry she said backing off my lips. “I don’t know what came over me. I’m such a bad person.”

“It’s okay…I understand Jillian...” Just as I was about to go into my next thought we both leaned into each other and started making out passionately on the couch. This was a moment I had only dreamed about. When I say I dreamed about it I mean it literally. I must have had a fantasy like this about her probably over 1,000 times if you actually went back and counted them all up. Ever since I met her I wanted this and it was finally happening. Yes I was engaged and getting married in a matter of months but at that moment I didn’t care. Nothing else mattered except locking lips with her.

When she finally pulled away she told me something that I’ll never forget. “He won’t be home until late tonight and I’ve imagined us doing this and a whole lot more for a long time.”

“Me too” I whispered to her. “I’m not just saying that either. I was always jealous of Chris. I’ve always wanted you.”

“Then take me…right now. We both want it” Jillian said as we got up and started walking toward the stairs up to her room.

When we got to the master bedroom we quickly stripped each others clothes off. When she got my pants off and my hard cock sprung free she took a deep breath as if to gasp. “Oh my” she said in disbelief. “This is what I have been missing all this time. Why didn’t you tell me how big it was?” Without waiting for my answer she dove face first into my cock and devoured it. She Licked it up and down, spit on it and sucked while she jerked me into her mouth. I had no idea how I would possibly hold out with the most beautiful woman I knew sucking my cock. “Does this thing actually fit in Ali?” Jillian said gasping for air.

“Yes it does and she seems to like how it stretches her out. But I’d rather see right now how it stretches you out” as I lifted her up by the arms and threw her down onto the bed.

“OH PLEASE…PUT IT IN ME NOW…I NEED IT.” Jillian roared as I climbed on top her and between her legs. I pushed her legs back a little and raised my hard cock above her already wet pussy and collapsed, driving my dick deep inside her.

“AHHHHHH…HOLY SHIT….YESSSSS!!!” She panted as her legs started to jerk on either side of me. Jillian started convulsing into her first orgasm in a matter of a few minutes and I was almost thrown over the top by her squeezing my cock. I pumped her hard and pumped her good. I felt my hard member hit the back of her tight hole and she moaned very loud every time I did it.

“OH GOD…FUCK ME…DON’T STOP…I NEED IT IN ME SO BAD. DO YOU HAVE ANY IDEA HOW MUCH BIGGER YOU ARE THAN CHRIS….AHHHHHHH!!”

That was it. I knew I couldn’t last longer than a few more seconds as she had me humping her even harder. Also the fact that she said I was bigger than Chris put me over the edge. He had always been more popular and had always gotten girls over me. Well, what goes around comes around as I had finally beaten him. I was on top of his wife and she was completely submitting to me in every way. I had finally won. I was slamming into Jillian, banging my body into her hips and was about to release all of my love juice inside her. I wasn’t sure whether she wanted me to cum in her or not but I knew I had to. I knew I had to plant my seed in this beautiful, fertile woman. Oh god, how I needed to send my baby batter up inside her. “Can I come in you? I’m really close” I managed to spit out in the throws of ecstasy.

“YESSS…CUM IN ME BABY…CUM IN ME RIGHT NOW…I WANT YOU TO GET ME PREGNANT! SHOW ME WHAT A REAL MAN DOES WHEN HE CUMS INSIDE A WOMAN” she said very seriously. She wanted a baby so bad and at that moment she wanted it from me.