I was 28 years old and never had sex. That is right. I grew up during high school living on a farm 30 miles away from the school. I didn't have money for a car. There are no regrets though. I made good grades and got a good scholarship into college. The only problem is that I was a little stunted when talking to girls. Even through college I didn't have the guts to flirt with women openly. I took this attitude into my career as well.
I got a good job at a growing company. By my second year I had 17 people working for me and I was achieving. Then a girl walked into my life. Her name was Debra. She was about 5'8". Thin with very small breasts, long legs and a butt that was just plain beautiful. She had blue eyes and long straight sandy brown hair. The most wonderful thing about her was her smile. I couldn't see her smile without cracking one myself.
How did we meet? She came to work. She moved from out of town right out of college. She trained on first shift and only saw her briefly in the morning. That first Saturday night I saw her at a local movie rental store. I talked to her briefly then I surprised myself. I asked if she wanted some company watching a movie. She sounded lonely and I was happy to just see her smile. She was beautiful without any makeup and I was hypnotized. She wasn't staying in town that night though. She was heading to see her parents and I was out of luck.
After her training she moved to my shift and we worked together. We had great chemistry together. Lots of laughs, lunches, and flirting.
One Friday morning we had been talking of going to play tennis after work. So one hot July morning we went to her apartments and played a set of tennis. It was SO hot. We were exhausted and went into her apartment for some air conditioning.
While in her apartment we went into her bedroom to get a towel. She has a long wooden bench in there that I thought looked odd. She said she liked it and kept it wherever she lived. I sat on it with a leg on each side of the bench. She then sat the same way only inches from me. I looked down at her breasts and noticed that her nipples were sticking out of her sports bra and could easily be seen in her sweat soaked sleeveless shirt. I quickly noticed that she had noticed what I was looking at. I was slightly embarrassed and she asked, "What are you looking at?" I responded (and I couldn't believe I said it), "You have been hiding those things from me." Her mouth came open and I continued "Your nipples look incredible and my mouth is watering." I knew that she was self conscious of her small breasts and the statement must have been magic. Right then she started to pull her shirt out of her sweat pants while saying, "How about a better look."
Now I have never been this close to a woman and I was pitching a major tent in my shorts. I reached over and placed my hand in the small of her back and pulled her close right after her shirt cleared her head. I felt her hair flow down and hit my face. With my other hand I reached around and undid her bra with ease (which I am still amazed of to this day). As the bra cleared her arms, she leaned back against my hand that was on her back. Like this I could feast my eyes on her breasts. They were small but very round and firm. But the amazing thing that made me almost explode in my shorts were her nipples stood out about an inch from her breasts. They were puffy and about big around as a quarter. I leaned over and took her left one into my mouth. I lightly sucked and flicked my tongue over it while my mouth never left the nipple. I then released it and kissed it gently while repeating the same exercise with the other nipple. After that she pushed my chest back. My part of the bench was against the wall and I leaned back against it. She ran her fingers down my chest to the elastic waistband of my shorts. With one quick swoosh she moved my shorts and underwear down below my hard dick. It sprang up and pointed right at her. Now my dick is not the longest (only about 7 inches). But it is very thick and today it was the hardest it has ever been. She paused at the sight of it and commented, "Wow! Look what you have been hiding from me." We both chuckled together. Right after the chuckle we kissed for the first time with my hand at the base of the back of her head and our lips meeting. The kiss quickly developed into mouth open, tongue twisting dance. At that time her hand went down and caressed my penis. I jerked back slightly. She asked if I was ok and I said, "Yes. Just be gentle." She stroked it about three times and I couldn't hold back. I thrust my hips forward at the first surge of my orgasm. The first spurt shot up over her shoulder. She looked shocked but didn't stop stroking (and I was glad she didn't). I spurted a second time straight up between us and we both watched as it apexed as we both were looking at each other. It then descended down and landed on her hand that was stroking me. The third went right up onto her right breast. The rest of my contractions were weaker but I must have gone about 10 times. She slowed down the stroking and started to rub her thumb over the head of my dick. I quickly jerked back out of her grasp and said, "Ooh, I am sensitive."