It happened two years ago, when my daughter graduated from high school. I had thrown a party for her and some of her friends on the night before she was to go away for a week at the Jersey shore, my graduation present. The shore trip is fairly common for grads around here. As the celebration was winding up, I mentioned that I was going to be stuck cleaning up the mess the next day by myself while she and her buddies would be off enjoying themselves. She just laughed and said that's life.
"Sometimes you get lucky, sometimes you don't. Tomorrow's my lucky day, not yours, I guess!" she teased.
"Well, that's gratitude," I joked, "for all my hard work. Kids today!"
Smiling she stepped forward and gave me a hug. "Love ya, Mom." Then almost as an afterthought, "If you're serious about needing help, I'll see if Tommy's doing anything tomorrow, he'll probably be glad to help."
Tommy was from the neighborhood, a nice 19 year old kid; I'd hired him before to cut grass and do odd jobs in previous summers. When I asked if he wasn't going away with the rest of the gang, she explained that since me had graduated the year before, he really wasn't part of the gang anymore, besides he was saving his money for the fall when he was going away to college. Smart kid I thought to myself. Then Lucy told me he kind of stuck to himself most times, and despite the fact that he was a nice guy and well liked, he didn't socialize much.
"No girlfriends?" I asked, because he wasn't a bad looking kid and well mannered.
"No, none, not that a few weren't interested."
"Don't think so, I think he likes girls, but he's maybe a little afraid of us, you know, the shy type."
With that she left, I saw her walk over to Tommy and begin talking. A few minutes later Tommy came over to me.
"Lucy said you might need some help in the morning, cleaning up. I'd be glad to help."
I told him it really wasn't that bad, but if he was free I'd be glad to pay him for his time. He assured me that would not be necessary.
"You paid for the party; it's the least I can do. Think of it as my way of paying back." He was that kind of a guy.
He came by the next morning to help, even though the mess wasn't as bad as it had seemed the previous night. I really hadn't needed any help, but I liked having someone to talk to while I worked, and I was curious about what Lucy had said about him at the party. He didn't seem to be the type who would have problems dealing with the opposite sex. As I said, he wasn't bad looking, but also neat, well spoken, polite, and smart. He seemed almost too good to be true. I still hadn't ruled out gay. After we stored the folding tables and chairs in the garage, hosed off the patio, and loaded the dishwasher, I decided it was time for a break. It was a hot morning, so we went into the kitchen where I got out a pitcher of iced tea and poured a couple of glasses. We sat at the table and talked while we cooled off. At first the conversation was pretty general; how did it feel to be out of high school, what college was he going to go, what was he going to study, and things of that nature. Then I slid in the question that was bothering me.
"Any girlfriends, Tommy?", I asked innocently, already knowing the answer.
He paused before answering, then "No, not really, at least not the way you mean it. I guess it's like that old saying, I've friends who are girls, but no girlfriends."
"Well, how can that be, you seem like the type that they'd flock to. You uncomfortable around them or something like that?"
"No, not exactly." He paused, looking at his glass as if there was an answer there. Then he looked at me, "I get along fine until I get by a girl that I really like, then I turn into a kind of idiot."
"How so?" I asked, deciding to press the issue.
"I get nervous, I guess. You know. I can't think straight and wind up making a fool of myself." He shrugged his shoulders slightly. It was beginning to make sense now, no confidence. He'd probably been rejected a couple of times when he was younger and never got over it: what a shame.
"Well, you have no problem talking with me, so I guess that means you don't like me?"
His head dropped for a moment before he realized I was just teasing him. Then he looked at me again and smiled, "There's no good answer to that. If I agree I insult you and if I disagree I come off looking like a 19 year old horn dog on a MILF hunt."
"That's a good answer!" There's nothing at all wrong with this guy, I thought to myself, nothing that his first woman won't fix. But, if he's this shy, it could be a long time before he gets lucky. Then the obvious answer came to me, I could be that first one. At his age I doubt if he could turn down a sure thing, and if he did back out, just being offered would probably be a boost to his ego. At his age, a 36 year old may have seemed like an old lady, but I was not an unattractive old lady, I figured he'd go for it. But how to go about it. I decided on the direct approach.
I got up and walked around the table and stood in front of his chair, looking down at him. "Stand up, Tommy." I said calmly, even though my heart was racing. He looked up as if he thought I was angry about the MILF remark, nothing could be farther from the truth. In fact, that was what gave me the idea; lucky him, lucky me, lucky us. He rose up nervously and stood in front of me. I reached up with one hand behind his neck and pulled his head down gently and kissed him lightly on the lips. Then with our lips inches apart I asked quietly, "Do you really think I'm a MILF?"
He didn't answer and I didn't care. It was on to the next step. Sliding my other arm around his back while I leaned against him, I pulled him tightly to me. Then I kissed him again, this time hard with my lips slightly parted. He kissed back but his lips were closed, no matter, he'd probably never kissed anyone before. I stiffened up my tongue and slowly pushed it into his mouth. His reaction was immediate and drastic: it was as if every muscle in his body tightened up at once, his own tongue came alive and began caressing mine, and I felt his dick hardening, pressing against my abdomen. I also felt myself starting to get wet; this was going to be fun. We stayed like that for several moments, lips locked, me grinding my hips against him, but I became concerned that he would cum in his pants if we stayed like that for too long. A dry hump wasn't what he needed or what I wanted. At this point I wanted a good fucking as bad as he needed one. I was really getting hot and I wanted this guy in me.
I broke the kiss and stepped back. Then, taking his hand I led him into the bedroom. It was cool in there; I'd left the air conditioner on low that morning and now I hoped it would cool Tommy off a bit as I'd like to get a little foreplay in before he went plowing into me. The bed wasn't made, but who was going to notice, besides, we were going to mess it up anyway. I thought about using condoms, being sexually active I keep some in my dresser, but if he'd never been kissed, then he'd never been laid so he was safe. Screw the rubbers. I figured his first time he should get the full treatment; let him fuck me "bare back", let him feel what it's like to cum in a woman not into a latex tube. We sat on the edge of the bed and I pulled his arm around my shoulders and faced him.
"I want this, honey, I want you. Just do as I say and it will be good. Good for both of us, OK?" He nodded in response. "Don't be nervous, relax and just let it happen."
With that I kissed him passionately while caressing his cheek hoping to give the throbbing hard on that I'd been grinding against in the kitchen time to chill a bit. Premature ejaculation is a bummer under any circumstances, but for a first timer with low self-esteem it could be disastrous. It seemed to be working as his breathing had become much more normal than it had been and his face was no longer flushed. That's it, I thought to myself, go slow sweetheart, relax and it will work out fine. Dealing with a horny first timer and making it more than a fast fuck was proving to be no small task.
While we kissed his hands started roaming over my body, it went to the usual places; feeling my tits through the bra, my ass, my inner thighs. Even though he was kind of awkward about it, it was really starting to turn me on big time. My pussy began to get wetter and stomach muscles were tightening as I got that tingly feeling that I get when my body is getting ready for a good screwing. When our lips parted I pushed him off me as gently as I could, I didn't want to do anything to discourage him. He sat and watched hungrily as I pulled my T-shirt over my head and tossed it on the floor. Then I reached behind my back unhooking my bra which joined the shirt on the floor. His eyes almost bugged out of his head as he looked at my naked tits. I am not large breasted, but I'm not flat chested either, and one of the benefits of having smaller tits is that they hold their shape well with a minimum of sagging, and mine are no exception. I imagine to him they looked like a million dollars. When I held out my arms to him he began first massaging them with his hands then kissing them, his tongue stroking my nipples, sending waves of pleasure through me. I lay back on the bed pulling him with me where he continued to work on my tits, occasionally moving up to kiss my neck and throat which I liked. He was learning quick. I took hold of his wrist and pushed it down my body, forcing the hand into my sweatpants and under my panties to my waiting pussy. I spread my thighs as far apart as I could to give him free access to my wet crack. My hand then slid over his and my middle finger guided his to my stiff little clitoris. My hips gave a quick small upward jerk when he pressed on it.
"That's it sweetie," I whispered breathlessly, "right there, the key to this; rub it, stroke it, what fucking ever, but that's what is going to get me off. Feel around, stick your finger in me if you want, but always come back to this."
He was a quick learner all right, and he took me at my word, bringing me closer and closer to an orgasm as his fingers alternately massaged and probed me. I kept thinking if a guy can make a woman cum the first time he ever screwed one it had to make him feel good, I know I was feeling great. I also figured it was time to lose the pants; it would be clumsy since I didn't want to interrupt him. Luckily I had kicked of my sneakers when we first came into the room so they were no problem. I arched my back, raising my ass off the bed and hooked my thumbs in the waist bands of the pants and panties and pushed them both down my thighs at once. Turns out I did interrupt him, I'd forgotten this was the first time he'd ever seen a cunt before, let alone one he was going get to fuck.