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.
She just burst into laughter and said “Steve, have you even kissed a girl before tonight? I mean really kissed a girl?”
I blanched, which gave her the answer before I even had a chance to speak.
“That’s what I thought. You are such a sweet, sweet young man.” As she said this she leaned forward and caressed my cheek.
“What I want,” She paused and ran her hand down my face, chest and back onto my cock, “is your virginity. Tonight. Now, as a matter of fact.” with that she stood and pulled me to my feet. As she led me to her bedroom she maintained a firm grip on my hand. She frequently looked back at me with the most beguiling news anchor smile she possessed. Right before we got to her room she looked down at my crotch and smiled again.
She turned and faced me. In her spike heels she was as tall as I was. She put her cool, smooth hands on my neck and pulled my face into hers. She kissed me softly at first and then opened her mouth. As our kiss deepened my hands slid down her back to her tight ass. I figured I had already been there so I gripped her ass hard. Immediately she moaned into my mouth and I felt her right leg slide up my thigh. She took her left hand off of my neck, slid down my arm, grabbed my hand and brought it up to her right breast. Instinctively I squeezed and again she moaned into my mouth as our deep osculation continued.
Linda lowered her foot back to the floor and both her hands moved from my thighs up to my chest. We broke our kiss. Linda’s green eyes had a wild look to them. Her hands were now on her top and she unbuttoned her top button. Suddenly she ripped her top open sending the remaining buttons flying. Her breasts stood out prominently, cupped by the white shelf bra that had until now been hidden under that jumpsuit. Other than a couple of titty bars this was the first time I had seen the real thing up close. They were a beautifully shaped pair of pert C-cups. It was a cool night and her nipples were erect and inviting. Linda saw that my attention had been diverted from the moment she had ripped her top open. “Do it. Suck them. Suck them hard, I want you to and God knows you want to.” as she said this she placed her left hand at the back of my neck and pulled me into her chest.
I gripped her petite body tightly at her waist and latched on to her left breast. As I sucked on her tits her body melted against mine. Linda’s right hand tightly squeezed my ass cheeks. Her left was behind my head pulling my head in tighter against her chest. “Harder, suck them harder.” she hissed.
I responded and she moaned and shucked off her top. I came up for air and she shoved the rest of her jumpsuit down to her ankles. She supported herself with her left hand on my shoulder as she stepped out of her clothes. Roughly she kicked them to the side before coming up against me for another kiss. The far wall was covered by a mirrored set of closet doors and I caught a glimpse of her as we kissed. God she looked good. Her strawberry blond hair cascaded over her shoulders, partially obscuring her large hoop earrings. I could feel her nipples pressing against my silk shirt and saw my hands on her heart shaped ass. She was still wearing the shelf bra, some white butt floss and those wicked looking white stilettos, one of which was raised in the classic female kissing pose. Linda began stripping me as we continued my first deep kiss. First she unbuckled my belt, opened my pants and shoved them down to the floor. I stepped out of them and we both moved toward her bed as we kissed. Suddenly she spun us around, broke the kiss and shoved me hard onto her bed. Slowly Linda got on all fours and crawled on top of me. “We’re going to fuck now Steven.” she said as she reached behind and grabbed my hardening cock.
“I don’t have any condoms and……” I began to stupidly blurt out before Linda covered my mouth with hers and kissed me deeply.
She then pulled slightly away, “Relax, I am protected. I don’t want you to wear a condom. I want to feel you come inside of me. Don’t hold try to hold back.” she said as she slowly guided my dick into her. Her eyes closed partially as she gently lowered herself onto me. I could not believe how good it felt when her ass was finally resting against my crotch, my dick buried to the hilt inside of her. She leaned forward and came off of me. Back and forth, faster and faster she was rode me. I started to move my hips in time with hers, meeting her thrusts with my own. “You feel sooo good. That’s it FUCK ME. Try and HURT me with your FUCKING cock.” she said as she rode me. It was the first time I had ever heard her even use the word fuck. Her dirty talk and her obvious lust was a real turn on. I was kind of shocked that I could cause a woman to talk, act and feel this way. She was getting louder and louder, “DO IT! FUCK ME MOTHERFUCKER! HARDER!” she was not quite shouting but it was loud and it was hastening my orgasm.
After only about ten thrusts I again felt the telltale sign of come starting to rise up my shaft. “Arggg, God Linda, I am going to come again.”
“Oh God! I am coming too! Don’t stop! Don’t stop! I want to feel you blow your load in me. Are you going to come for me? Are you?” she asked as she rode me harder and harder.
I was still too stunned to really match her in the dirt talk department and I think all I managed were a couple of weak ass “Yeses”.
Linda bottomed out on me, stopped thrusting and rolled us over so that I was on top of her. “Pound me! Drive your fucking cock deep into my tight pussy!” she said as she both crossed her legs and pulled them forward toward her chest tightening up her pussy.
She was underneath me now and I started to fuck her, slowly at first but then picking up to our original rhythm. Moments after switching to this new position I again felt the come beginning to rise. “God Linda, here I come.” was about the most I was able to squeeze out as I began shooting twenty years of pent up come into her.
“Oh God Yes! Fill me. Call me a bitch!” she said.
I had been right on the line and this started to push me over but Linda was now just about screaming at me. “DO IT! CALL ME YOUR BITCH! DO IT!”
As the come started to flow I finally started to loosen up a little and complied; “God yes you are one fucking hot bitch< />! I have wanted to fuck you from the first time I saw you on the news! ARGG! I shot my load into her and collapsed, spent and finally relieved of my virginal blue balls.
We started kissing again and ended up fucking twice more that night.
It was the start of an on again off again relationship that would last almost twelve years and give me an education that shy boys do not get in either high school or college.
