A little backstory on how I ended up in my situation. My name is Steve and I am 25. I am a college educated guy who works in finance. I really never had much luck with the ladies during college other than a few one night stands. I'm 5'9" tall with a slim swimmer's body. I'm also average in the cock department being around 6" long and average girth from what I've seen in locker rooms at the gym.
I first laid eyes on Rebecca, or Bec for short one night while I was out at a bar. We instantly hit it off and I loved her long blonde hair and green eyes. She was very engaging and we ended up talking for a while before we left and went to a small local coffee shop and talked for a few more hours.
She was 24 and had a totally different history than I did. While in highschool she fell in love with her highschool sweetheart. At the end of her senior year she ended up pregnant so they got married. She ended up working at a local department store and he worked at a manufacturing plant. They were together for a few years and then he surprised her by saying he wasn't ready to be a father or a husband, divorced her and left town. Now all she sees of him is a card at the holidays and on their son's birthday with some money in it.
It was a sad situation but the way she took it in stride and had just kept going amazed me. Everything about her was exactly what I had been looking for.
Bec was 5'6" with a thin body. She has a nice C size breasts but she didn't seem to overshow what she looked like. The more we talked, the more I fell for her.
That first conversation led to a few more dates where we would just sit and talk. Neither was in a rush and we both were honest and open with each other. She told me that her ex was her only sexual partner and it had all been really vanilla with mainly missionary in a bed.
I on the other hand had been with several partners and some of them had really stretched my comfort zone with different positions in all kinds of situations from outside in a park to actually having a girl ride me cowgirl in a dark corner of a frat house with others around at a party.
She was always asking questions about my past, how each position felt and what it was like. She really wanted to open up sexually but with a small son she was always very conservative, which was understandable.
It was almost a month before we made out on her couch one night and I went down on her. She tasted amazing and after a few minutes had an orgasm while gripping the back of my head. After that she thanked me and said that she wasn't ready to go all the way but wanted to return the favor. She had me stand up while she nervously unbuckled my pants and pulled out my cock. As she held it and it started to grow she looked up at me with a grin. Just then, she reached out and licked it from my balls to the tip. The feeling was amazing. Just when I thought it couldn't get any better she grabbed and and started to suck the tip into her mouth. She finally closed her eyes and started to do a long slow suck on me.
The more she did the better it felt. After a few minutes I ended up reaching down and grabbing the back of her hear and slowly fucked her mouth. She instantly started to moan as I did. The closer I got, the faster I stroked in and out of her mouth. She latched down with her mouth and was constantly moaning. I finally let her know that I was going to cum and she just kept going. Finally when I came she swallowed as quickly as she could.
Once I had finished and started to soften, my cock slipped out of her mouth and I fell back on her couch out of breath. She just slid up beside me, still in her bra and shirt, with her panties and skirt on the ground while my limp dick fell to the side and my pants were around my ankles. It was heaven while we cuddled.
As we were laying there she let me know that was the first time she had an orgasm from someone going down on her. Her ex would never do that and either wanted to just climb on top of her to get himself off or have her quickly give him a blowjob. Her sexual experience was limited but she enjoyed testing her boundaries and trying new things. She really enjoyed me fucking her face because she had never experienced that either. She generally would be asked to lick him until it was wet and jack him off while he sat back with his eyes closed. That's when she told me she was hesitate to go further with me because I was longer than her ex. That shocked me considering I wasn't that big or thick. So no wonder she almost never had an orgasm unless she did it herself.
That night was a turning point for us. After that I went out quite a bit with her and her son. we started hanging out and a few weeks later once she put him to bed she asked me to spend the night. I couldn't agree fast enough.
The first time that we had sex it was missionary and very slow. We took our time and enjoyed each others bodies. I found out that she really loved her nipples being sucked and really got off on looking face to face while we fucked.
The next morning wasn't as awkward as I thought it would be around her son, so it took the edge off of everything. I was the first one up so as I started to make coffee he came in the room and I made him some cereal. We were talking about the cartoon that was on when she came out of the bedroom. She was in a big T-shirt and panties and looked more beautiful than I had ever imagined. She just grinned at me and poured a cup of coffee.
After that first night, I started staying over three or four times a week. She was always up to try something new. Her favorite new position was doggy style. She really liked it when I would pull her hair while I hammered into her. She ended up screaming an orgasm into a pillow so she didn't wake up the whole apartment complex.
After about six months we had started a familiar routine. We would have amazing sex, using different positions, toys I had bought, blindfolds and anything else we could think of. She was really getting into her own and was even dressing sexier. She was generally wear tight fitting jeans but started wearing tops that were cut lower and lower showing more and more cleavage. She loved to see the lust in my eyes every time I saw her.
Then the day happened that changed it all. She came home after work and I had been making dinner for us. She said that she got pulled over for speeding, but got out of it with a sort of warning. I asked her what that meant as she poured a glass of wine and drank a few sips.
She said that the officer was a really good looking guy who really took a liking to her. They talked while he ran her license. He then said that he would love to take her to dinner and see what he could do to make the ticket go away. So she gave him her phone number and then he introduced himself as Ben.
I didn't know what to say but that night we had mind blowing sex. As we were sitting there in the afterglow I brought up that Ben had her number and what would she do if he called. She really never answered me straight forward. So I asked her if she thought he was sexy and I slid between her legs. Since we always used a condom, there was no remnant of our first encounter so I just started to lick her. I knew i was on the right track as she started to moan. I started asking questions as I kept licking and using my fingers to get her excited.
"Did you like the attention and the way he looked at you?"
"yes......"
"Did you think he was attractive?"
"yes....."
"Did you imagine what it would be like to kiss him?"
"Maybe...."
"Be honest, did you imagine screwing him?" as I slid a finger in t was wetter than usual.
"Okay, yes, I thought about it and got wet thinking about it."
