When I was a junior in college, I got a part-time job doing computer work at a small consulting firm. It was a friendly, informal group - the founder, a handful of consultants, the office secretary, and me. The secretary, Patty, quickly became the object of many of my fantasies. She was in her early 40's, with short chestnut brown hair, green eyes, maybe 5'4", and slim, but voluptuously curvy. She was divorced and the mother of a teenage boy. We hit it off well, and quickly became friendly.
A little bit about myself - I was six feet tall, slim to the point of skinny, brown hair, blue eyes. I was very shy, and had no self-confidence around girls. I had dated some, and wasn't technically a virgin - I had had some very nice make-out and foreplay experiences, and even a couple fumbling tries at intercourse - but they were dark, scary, quickly-over experiences and didn't do anything to boost my lacking self-confidence. Many of my fantasies were about being "shown the ropes" by an older, more experienced woman, and Patty fit my fantasy perfectly.
In the course of our working relationship, we learned more about each other. She would ask about my love life, and I would lament what I felt to be my lack of charm and social skills. She would reassure me that I was smart and handsome and that there had to be plenty of girls who would be happy to be with me, which was nice to hear. She would complain about her lack of a love life, and I would always be stunned that there weren't men lined up for her.
I really had no thought that anything would happen between us. She was totally "out of my league". And I had heard her say on more than one occasion that she would never get involved in an office romance. And that was fine with me - working in close proximity to her provided plenty of fuel for my very active imagination. The tight sweaters she wore in the winter showed off her full round breasts perfectly, and some of the sun-dresses she wore in the summer were so clingy and tastefully low-cut that it was all I could do not to stare slack-jawed.
I know she knew how much I admired her body, and I think she appreciated the attention. I tried not to stare openly, but I always took advantage of any opportunities I could get to look without being noticed. My favorite times were when I had to help her troubleshoot a problem at her desk and she would be wearing something low-cut. She would be sitting at her desk, and I would be standing behind her trying to determine what was wrong - and getting the best view I possibly could down her blouse. She had to be a D-cup, and I would just stare at those ample breasts and dream of exploring them with my hands and my tongue.
My twenty-first birthday was a Friday in June. The rest of the guys were at a client in another state, so it was just Patty and me. There was a celebration planned for after they got back next week, but Patty insisted that the two of us celebrate on my actual birthday. We ordered a pizza and had jug wine in plastic cups, which was the usual birthday celebration. As it was a summer Friday afternoon with the bosses away, we were in no hurry to get back to work, so we kicked off our shoes, talked some more, and drank a few more cups of wine. She was wearing one of the sun-dresses that had me forever pushing the envelope of how much I could stare without getting caught.
She was telling a story about a relationship that hadn't worked out, and I think the wine made me careless - I was just mesmerized by how her breasts moved whenever she shifted positions. I realized she had stopped talking and I looked up and met her eye - I was caught! My heart jumped into my throat, and I'm sure the look on my face was pure panic. I expected her to be angry, but instead she gave a little smile of amusement. I was still expecting doom to fall, but she stood up, extended her hand, and said, "Come with me." I took her hand, and she led me into the boss's office, sat on the couch and drew me beside her. I started to apologize, but she put a finger to my lips to stop me.
"I see how you look at me, and I'm flattered. You're a sweet boy."
She took me in her arms and drew my face to hers for a kiss, once lightly, then again more passionately. I felt her mouth open and her tongue slid into my mouth, finding mine. She broke the kiss and looked at me with a smile. She laid halfway back and drew me to her. This time I kissed her, and with urgency. I was trying to drink in this sexy woman with all my senses.
I think I would have kissed her forever and never taken it any farther, but thankfully she had other ideas. She took my hand and placed it on her breast. My god, I thought I had died and gone to heaven. I rubbed and squeezed her breast through the thin dress, and I heard her moan into my mouth. I could feel her nipple harden under my touch, and I wanted nothing more in the world than to suck them. Her hands were running over my back and chest, first over, and then under my shirt.
She broke the kiss and lay back a little farther, smiling and unbuttoning the top button of her dress. I could now see her powder-blue lacy bra, and when she undid the next button I could see the full swell of her breasts and her dark nipples poking out. I was totally mesmerized as she slowly revealed herself to me. When she undid the last button, she stood up and let the dress slide off her shoulders, I could see that she had on matching blue low-cut lacy panties. I could see the dark triangle of her pubic bush, and I could smell her arousal.
She took my hand and stood me up, and we kissed again, deeply and urgently. My hands moved to the clasp of her bra, but she whispered, "Wait just a minute. Let me undress you first."
She took my shirt up over my head and off, then moved close enough to rub her lacy breasts against my bare chest. It was an incredible feeling and an incredible sight. Then she whispered, "Now take my bra off".
I undid the clasp and slid the straps down her shoulders. She stepped back, and it fell to the floor. She cupped her breasts in her hands, smiled at me, and asked, "You like?"
I was too stunned to answer and just nodded my head dumbly. They were everything I had imagined over the past months - big, round, and full, with dark-red nipples that stuck out at least half an inch. I was aching to touch her, but I guess I was still waiting for her permission. She motioned for me to sit down, and then she straddled me on the couch, kissing me deeply while my hands finally found their way to those big breasts. I took one in each hand, feeling their weight and their softness. I rolled her nipples between my thumb and finger and heard a moan from deep in her throat. She presented her neck to me, so I kissed and sucked it while my hands continued squeezing.
She moved up on me, and her breasts were now in my face. "Go ahead and suck them sweetie. I know that's what you've been dreaming of."
She couldn't have been more right. I licked and sucked one breast and then the other. I couldn't get enough of those big hard nipples, and I sucked them with all my energy. Patty was going crazy, holding my head to her breast and telling me how good it felt. She was also dry humping me through the layers of clothes, which was becoming uncomfortable.
Suddenly she stood up and backed away from me. My face must have shown my disappointment, because she laughed, "Don't worry, we're not done." She told me to stand up and came into my arms, kissing me softly and letting me feel her breasts pressed against my chest. Then she sat down and motioned me to stand in front of her. She kissed my chest and stomach, undoing my belt and unbuttoning my pants. Unzipping me, she let my pants fall to my ankles, and I stepped out of them. Needless to say, at this point my cock was as hard as steel and was throbbing for release.
I stood in front of her as she stroked me through my briefs. I knew from pre-teen comparisons with some of the neighborhood guys that I was somewhat larger than average (or at least the average of the neighborhood guys), but I was nervous about having the proper equipment to satisfy a woman. I needn't have worried. As she slid my briefs down over my hips and off, she literally gasped. "My god, who knew you were hiding that all this time?"
She cupped my balls with one hand while the other stroked my shaft from the base up to the head, then back down. Then, looking me in the eye, she licked slowly up and down the shaft. Then she licked the underside from my balls all the say up to the head, circling the head with her tongue but still not taking me in her mouth. She did the same thing again, but this time she closed her lips around the head and sucked it in. She rolled her tongue around it then took in as much as she could. I felt like I had been plugged into an electric socket, and she had to know I couldn't hold off much longer. I moaned "Oh, Patty!" and she bobbed her head up and down a couple more times quickly, then wrapped her soft tits around my cock. I came like I've never come before, spurt after spurt of my hot cum splashing onto her breasts.
I was afraid she might be upset with me for not lasting longer, but of course she understood. I watched as she sensuously massaged my cum into her breasts and belly. Then she asked me to sit, and stood in front of me. She brought my hands to her hips, and I took the hint, sliding her panties down and off.
She was naked in front of me, and so beautiful. She had a thick brown bush, and I could see that she was very wet. I hesitated, and she whispered, "Touch me." I stroked her belly, then downward, running my fingers through her bush. She lay down beside me and put one knee up so I could have a better view. She spread her legs a little, and I could see her pussy lips start to open. I traced her lips with my index finger, then slid it inside her. She was warm and wet and it slid right in. I slid it around and then traced up to her clit, circling it quickly. She closed her eyes and pulled on her nipples as I explored her with my fingers.
The best thing about being 21 is the recovery time. I was so turned on by exploring her body that my cock was coming back to life. She noticed, and she smiled and moaned "unbelievable". She drew me up into a deep tongue kiss and spread her legs wide. I could feel the heat of her pussy against the shaft of my cock.
As incredible as this had been, the thought of what was about to happen had me a little scared. I'd been to this point before and things had gone badly, and I had doubts about whether or not I could satisfy a "real woman". I wanted so badly to feel like a real man. And I didn't want to disappoint her.
I'm sure my face betrayed all these thoughts. She held my face in her hands and whispered, "Relax, lover, I want to show you what real lovemaking is like."
She took my cock firmly in one hand and rubbed my head around her entrance, getting me lubed and positioned at her entrance. She moved her hips and the head of my cock slid inside her. We both moaned out loud as she moved her hips again and the entire length of my cock disappeared into her pussy. I felt like I'd been struck by lightning. She wrapped her legs around me and I thrust forward into her. I tentatively withdrew partly and slid back into her, fireworks going off in my brain. She could feel my hesitation and whispered "Don't worry, baby, you're not going to hurt me. Give it to me good."
That was all I needed to hear. I thrust into her tight wet pussy again and again. The feel of my cock sliding into her pussy until I was balls deep was the most incredible thing I'd ever experienced. I kissed her urgently, the thrusts of my tongue into her mouth matching the thrusts of my cock into her pussy.
She shifted position and said, "Let's try something else." She sat me up on the couch and straddled me, taking my cock in her hand and lowering herself down onto me. I thrust upward as she sat down on me and we both groaned out loud. She was in control now, moving on me first with quick short strokes, then with slow deep strokes. She would feed one breast and then the other into my mouth, telling me how much she loved having her nipples sucked. She could feel when I would start to get close, as she'd slow down to a maddening pace. I tried to drink in every sensation - the look of ecstasy on her face, the moans of pleasure when my cock hit bottom inside her, the way her breasts bounced as she rode me, the smell of her pussy on my fingers.
Finally she could tell by my grunting that I was reaching the point of no return. I grabbed her hips and thrust up into her as she bounced frantically up and down on my throbbing cock. She screamed in orgasm as I shot my load into her hot pussy. She kissed me again and again, telling me what a good lover I was, as I felt waves of satiation and happiness wash over me.
I truly felt like I became a man that day. I'd like to say that we stayed lovers, but it didn't happen. It was a magic moment, but she felt it would have made work uncomfortable, especially with the difference in our ages. I was disappointed but understood, and she moved out of town a short while later. But I'll always be grateful to her and will never forget my birthday present.