I was a shy guy in high school and I never dated until well after graduation. I also suffered from a distinct lack of "game". My conversation turned wooden in bars and other social venues thus impeding my ability to hook up.
During the summer after my freshman year of college I was lucky and landed an internship at a local T.V. station. One of the anchors for whom I worked was a thirty-six year old blonde named Linda. She was about two years out from a divorce that had hit her self esteem really hard. I was unaware of that at the time but I occasionally flirted with her while we worked. Though I was tongue tied in bars, at work I could function socially. It even got to the point where I would touch her regularly. She would complain of a stiff neck or shoulders and I would giver her a back massage while she sat at her desk. Though not a big deal to most guys this was as close to action as I ever saw.
Linda was average looking, for a news anchor that is. In my opinion most female talking heads are just a twist of fate away from being porn stars. She usually wore well tailored Liz Claiborne suits and she had a great body.
Every now and then I would walk Linda out to her car when we both left for the evening. During one of these walks to her car she said that she wanted me to come over to her house the next week so that she could cook me dinner. I was pretty surprised as I really did not think she was interested but told her I would definitely be there.
Next week Friday found me pulling into Linda's driveway. I was not yet twenty-one so a bottle of wine was out but I did at least bring her flowers. When the door opened she was smiling brightly. A form fitting, one piece blue corduroy jumpsuit tightly covered her body. It accentuated her curves nicely and though it covered almost everything I thought that it was pretty sexy. She was wearing more makeup than she ever wore at the office and a pair of five-inch, white pumps pushed her ass up nicely.
It turned out that she could cook and after a really good dinner we sat in her family room and talked. At some point I thought I heard my cue to pack it in and I made a move to go.
She grasped my hand and while pulling me up from the couch said, "Before you go why don't you give me a massage. Let's go to the living room where there is more room and we can spread out on the floor."
I had no idea if this was going to lead anywhere, or not, but I was not about to pass up an opportunity.
Linda started out by lying face down on the floor. I was unsure of what to do and took several steps back and forth.
"Just straddle me sweetie." she said with an innocent smile.
So I did. I sat on her ass and proceeded to rub her back, shoulders and neck. After about fifteen minutes I moved down and began massaging her legs as well. I started with her calves and moved up. I was close to her ass and was about to jump back to her neck when she said, "Oooh yea, get my ass too."
I started kneading her ass and this generated a series of sexiest moans I had yet heard come out of a real woman. I eventually moved up her back and shoulders but worked over her entire body about three more times, lingering at her ass each time.
"God, that was good." She said as she rose up on her elbow and turned, partially facing me. "Let me return the favor. Help me up." She commanded and I took her hand, helping her to stand. She was now facing me, only inches away. Her voice was very soft now. "Your turn, lie down Steve."
She started out by straddling me much the same way I had started out on her. After my back and shoulders she slid down and began working my ass. She nudged my legs apart and I felt her hand and nails graze my crotch. I had to stifle an involuntary desire to jump at her touch. I had been too nervous to be hard up until now but suddenly I had a raging hard-on.
After a while she stopped and moved to the side. "Roll over" she said softly.
I did and she gripped both of my ankles and began messaging up the length of my legs. When she got to my thighs instead of messaging she was running her long nails over the denim of my jeans. This transmitted the most amazing sensation. Slowly she began tracing the outline of my cock with her nails.
I was excited and at the same time terrified I would do something to derail what I though might be happening. I completely froze.
Linda had been looking at my crotch but she shifted her gaze and our eyes met. She was softly biting her lip and looked like she was trying to decide something. She stopped biting her lip and broke our stare.
The sensation of my zipper going down reverberated through my body and it seemed like the noise filled the room. I was young, very naive and the first thing that went through my mind is that I was not wearing underwear and I hoped this would not shock her. God I was an idiot.
She extracted my hard cock and I inhaled sharply. This caused Linda to look up and once again our eyes met. While still looking at me she brought her left foot up and placed it just outside my right thigh. Her weight was now supported by her right knee and left leg. Slowly she lowered her head until her mouth was less than an inch from the end of my cock. I could actually feel her breath. She held here for second, broke eye contact and slowly engulfed my cock. The sensation was almost as amazing as the sight of this hot thirty six year old going down on me. Linda had seemed like such the girl next door type I had never imagined what was now happening. She was actually deep throating me, her lips coming up against my denim fly. She had a death grip on my thighs and I could feel each of her nails as they dug into my jeans.
She stopped for a moment, "This is your first blow job, isn't it Steve?" she asked.
Breathily I managed, "Yes, and I am going to come really soon here."
She laughed and said, "I am sure that you are. I have been thinking about swallowing your come since the moment I saw your ass in these jeans. I know that this is your first time and I want you to really let go. Put both of your hands on my head and when you need to come just force it down my throat. I love to be manhandled."
I was blown away. It was not how I had expected the evening to unfold.
Linda then shifted so that she was kneeling in between my outstretched legs. This time she maintained eye contact as she impaled her mouth on my cock. Soon I felt the telltale signs of come rising and I gently placed my hands on her head. As I started to come I took her at her word and forced her head down so that my cock was deep in her throat. As I came I released her and forced her down three more times.
"God that was good. I really, really like oral sex." She said with a very innocent looking smile as she sat up on her heels.
This was all new to me and I was out of my element. "Thank you. Should I return the favor?" I regretted it the second it was out of my mouth but it was too late.
