I met Lilly on a business trip to Texas more than 10 years ago. She was recently divorced and out celebrating her new freedom with a group of friends. As luck would have it, I was in the right place at the right time. It had been almost a year since the last time she had sex and had decided that some lucky guy was going to help her ring in her divorce with some good old fashion commitment-free sex.
At the end of the night it was lucky Pierre (me) who took home Lilly for said meaningless sex. I was in town for business and had decided to unwind with a couple of drinks in the hotel bar. I'll never forget the moment she walked into the place.
Years later when she confessed she was there to get laid, I laughed that she was lucky I had wandered it, as it would have otherwise been between a guy who weighed more than 400 pounds and a 60 year-old drunk.
What should have been one night of fantastic sex, turned into something more. Lilly and I had an immediate connection. Our conversation popped, the chemistry between us was electric. The lovemaking was incredible. It was as if we were locked into each other's sexual ebb and flow.
I wasn't exactly a teenager at the time, but I went all night, as Lilly had 12 months of sexual frustrations to make up for. While having sex the first time can often be clumsy and embarrassing, Lilly and I found an immediate rhythm. She was full figured, but without an extra ounce of fat on her. Well into our third go round, as she was seductively riding me, I looked up at her beautiful face as I squeezed her breasts into my hands and wondered how anyone could leave a woman like her.
We awoke the following morning in my hotel room with very little awkwardness. I invited her out for breakfast. We spent that Saturday morning talking like old friends. I had a flight out that afternoon, but we promised we'd keep in touch.
Keep in touch we did, via e-mail and phone calls. It was then that Lilly told me about her 10 year old daughter. As a general rule, this would have been a deal breaker for me, but Lilly was no ordinary woman. After six months of a long distance relationship, Lilly and I decided to move in together.
Madison, Lilly's daughter, and I got along OK, but not great. She actually cried the day Lilly told her we were getting married. Over time, Madison's father started a new family and perhaps she decided to fill that hole in her life with me, or perhaps we just learned to live together. Regardless, we began to get along well.
After four years of wedded bliss, Lilly and Madison were involved in a horrendous car accident caused of course by a drunk driver. Madison survived relatively unscathed. Lilly was not as fortunate. In the darkest day of my life, Lilly was killed instantly. We had recently celebrated the fifth anniversary of the day we had met. On that day she had asked that I take care of Madison should anything ever happen to her. As she was only 35, I laughed and said she would certainly out live me, but that it would be an honor.
As luck would have it Madison's father didn't want anything to do with her. He relinquished his rights and I ended up adopting her. Madison was 14 years old and was hitting puberty. We had a very rough patch as I had no idea how to raise a teenage daughter and Madison suffered from severe nightmares regarding the accident.
On more than one occasion she would ask to sleep in my bed because she was so scared. My heart went out to her knowing that in some respects the person who loved her the most in the world was now gone. At this point I made the decision to sacrifice whatever I had to to give Madison the best life possible.
This wasn't always easy however. She was a teenage girl after all, and I didn't know anything about teenage girls. Somehow we made it to her 18th birthday. She was almost finished with high school and had decided to go to college out of state.
I was excited for her, but also sad. The person I had centered my life around for the past four years was leaving. I had had almost no social life during this time, and had in fact only had sex twice, as a co-worker threw me a couple of mercy fucks for my 38th and 39th birthdays.
On the weekend after Madison's birthday, she asked to go out with some friends.
"You can go if you promise me there'll be no drinking," I said.
"How can you even say that after what happened to mom, dad!" Madison screamed at me. "I would never do that!"
Not surprisingly, the doorbell rang at almost 3 a.m. I was in a half panic as Madison's curfew was 12 a.m. She was stinking drunk; almost falling over. When the door opened the car containing her jackass friends sped off.
I was furious, but Madison was such a mess, I didn't think it would do any good to lecture her at the moment. She smelled of vomit, was covered with mud, and could barely stand. I told her to go clean up and go straight to bed.
A few minutes later she stumbled into my darkened bedroom.
"Dad, I don't feel so good... can I sleep here?" she said.
"You smell like crap, and I'm not in the mood to have to wash my sheets tomorrow. So no," I said.
Madison began to cry. "I'm sorry dad. I really am. I don't know what happened. I just had a couple of beers, and then I really began to miss mom. I just don't feel good. Please?"
"OK, but this isn't over," I said. Madison plopped down on my bed and got under the covers. A few minutes later I decided to go sleep on the couch as I honestly could not deal with the smell.
I woke up at 6 a.m. and took my Saturday morning run. I was extra tired as I had not gotten more than a few hours of sleep the night before. I tried to think about how I would deal with the situation. While taking a shower, I decided I would give the kid one free pass.
After showering, I went to check on Madison. The sun was creeping into my bedroom and I saw her lying there on my bed with all the covers kicked off. She was wearing a thin pair of bikini briefs and a very tight white muscle shirt.
My mouth dropped open as I had never really had the opportunity to see my stepdaughter's body like this. Outside of a bathing suit, I had never really seen much of her body at all. I got closer to the bed and said "Get up Madison, we need to talk about what happened," in a stern voice. She didn't even budge. I sat next to her on the bed and continued to examine her body. She was lying on her back. He breasts were large and firm. Her hard nipples were poking through the shear t-shirt material. The sides of her breasts were spilling out the sides of the shirt in fact.
Her legs looked smooth and were slightly tanned. My eyes followed her legs from her feet upward. She had tufts of thick, black, curly pubic hair escaping from the small cotton triangle. There was a thin trail of hair leading from her pubic area to her belly button, I could see as her t-shirt was riding up.
It was at this moment that I realized I was hard as a rock. My breathing was heavy, and I was so nervous I was actually getting light headed. I was only wearing a t-shirt and underwear. I found my dick and gave it a squeeze. I grew braver and placed my hand on her the thickest part of her thigh. As I brought my hand across her leg, goose bumps followed the trail created by my hand.
Madison didn't react to this. I reached out and gently tugged at her pubic hair. Again, no response. I continued to do this for a few minutes. At this point, I knew I was nearing the point of no return. My hand continued up her body until it reached her breasts. I gently squeezed both breasts and rolled her nipples between my thumb and finger. After a few minutes of this, Madison moaned and shifted positions.
I very cowardly jumped from the bed and jumped back into my bathroom. When I noticed that she was still asleep, I went back to the bed and sat besides her sleeping body. She had turned around, affording me a perfect view of her full ass. Her briefs were riding up her cheeks. I massaged her ass cheeks for a few minutes.
I then pulled out my hard cock and began to stroke it. Madison resembled Lilly in most ways and it had been so long since I had been with a woman. This is the way I justified it at least. After just a few minutes I felt my climax approaching. Throwing all caution into the wind, I aimed my hard dick at Madison's voluptuous ass and shot stream after stream of hot cum onto her luscious ass.
Madison did not react to any of this, sleeping through it all. In fact I jacked off next her another two times in the next hour. I cleaned her up and let her sleep it off. She finally awoke later that afternoon.
We had a long conversation about the dangers of drinking that afternoon, and I told her she was getting a freebie, but there would be hell to pay if there was ever a next time.
The real problem, at least for me, was the fact I was now completely infatuated with my teenage stepdaughter. I found myself purposely peeking in on her at every opportunity. This wasn't easy as I had worked hard to instill a sense of modesty in her. Sure she tried to get away with the occasional short skirt or skimpy top, but for the most part I found I had done my job much too well.
About a month after the drunken incident I decided to throw some gasoline on the fire and began to walk around in my underwear. I usually wore thin boxer briefs, but again, in an attempt to raise my stepdaughter modestly, usually always wore a robe or pajamas in the house. One Saturday morning I walked down from my shower in just my briefs. I strolled into the kitchen and grabbed a bottle of water from the fridge.
Madison was seated at the bar eating cereal.
"Dad!" she exclaimed. "I didn't know that sausage was on the menu for breakfast!"
I genuinely found myself blushing, but without missing a beat responded: "Look, you're 18 years old now. You're an adult, and I'm an adult. You're leaving home in a few months, and I have no doubt you'll be seeing much worse in the co-ed dorm you'll be living in. Seeing me in my underwear isn't going to make you a pervert or anything. Plus, I pretty much saw you in all your glory last month after you came home toasted."
I gave her a little smile, and it was her turn to blush.
"What did you see?" she asked.
"What didn't I see is the question," I laughed. With that I left the kitchen.
