Not many people can believe that I was 20 years old before I lost my virginity. I couldn’t believe it either, and I got increasingly nervous as my teenage years passed by one by one without me getting laid. It wasn’t that I was unattractive or unlikable I was just really shy, which sometimes made people think that I was a stuck-up bitch. Guys never really approached me, and I was completely incapable of pursuing them.
I worked at a clothing store one summer to help put myself through college, and when a group of us from work would go out after our shift was over, I was totally fine and at ease. But if I was ever left alone with a guy—especially if it was Adam, whom I had the biggest crush on—I would morph into a social reject. Adam was two years older than me, and I’d had a crush on him since I was a sophomore in high school. He was always really nice to me, but didn’t seem to think of me romantically. We worked a couple of shifts a week together, and somehow I always found myself around closing time having these very erotic fantasies involving the two of us in one of the dressing rooms.
I had convinced myself that Adam was the perfect guy to take my virginity the only problem was that I was scared shitless, since I had no experience with the opposite sex. I mean, I got my first kiss when I was 18, and the guy didn’t even try to feel me up! I felt completely hopeless, and was sure I would die a virgin. Then one evening my boss called me at home to ask if I could work an extra shift for one of the girls who was out sick.
Earlier that evening my parents had gone out to dinner, leaving me at home with their wine collection. I knew that one missing bottle would go undetected, so I helped myself to some good cabernet, hoping to make myself feel better about my pathetic social life. When my cell phone rang and I saw that it was my boss, Tommy, I got a little nervous, hoping the wine wouldn’t make me slur my words too badly.
Tommy was so far out of my league that it had never even occurred to me to have a crush on him. He was about 10 years older than I was, and was probably the sexiest man I had ever met. All the girls at work gossiped about how hot he was, but I don’t think any of them thought they had a chance. As far as we knew he was single, but he never talked about his personal life at work.
“Hey, Allie,” he said when I answered. “Sorry to bother you at home, but I was wondering if you could do me a favor.”
“Sure,” I replied.
“Megan can’t come in to work on Thursday, so I was hoping you would be able to pick up her shift,” he told me.
I knew I had nothing to do on Thursday night. Just like most nights. I let out a big sigh as I informed him that I was available.
“Is everything okay, Allie?” he asked then. “You don’t sound like your usual cheery self.”
Already two glasses into my bottle of wine and feeling a good deal less inhibited than usual, I confessed to Tommy that I was really depressed about my social life.
“Why?” he asked me. “You’re such a great girl, and you have so much going for you.”
I knew he was trying to cheer me up, but I was just so sick and tired of hearing what a great person I was, while still feeling like the most undesirable girl on earth. “Thanks, Tommy,” I said, “but a pep talk isn’t exactly what I need.”
“So what is it that you need, Allie?” he inquired. Now I might not have known much about sex or even dating, but the tone of Tommy’s voice was unmistakable—he was totally flirting with me. I had no idea how to respond, though, so I just stayed silent. But that didn’t seem to deter him, and he asked again, “What is it, Allie? What is it that you need?”
I guess the combination of the wine and my increasing excitement level made me throw caution to the winds. “I need to learn how to be with a guy, Tommy, okay?” I blurted out. “I’ve never done anything more than just kiss one.”
There was a few seconds of silence, and I figured that I had completely misunderstood his question, and would now have to quit my job out of sheer embarrassment, since I could surely never face Tommy again. But when he finally spoke, I could actually hear him smiling. “It sounds like you just need a good teacher, Allie,” he said. “Would you like me to teach you?”
I felt my pussy start to tingle. I couldn’t think of anything I wanted more than for Tommy to teach me everything I needed to know about sex! “Yes, Tommy,” I answered boldly. “Yes, I would love for you to teach me.”
“Good,” he said. “Wear something sexy and be at my house in half an hour.” He then gave me directions to his place and told me not to be nervous, that we were going to have a great time.
Not be nervous? Easier said than done! I had waited 20 years for this, and now I was about to get naked with the most unlikely person imaginable. Unlikely, but so fucking hot! Nervous or not, I couldn’t wait to get over there. I really couldn’t believe that this was about to happen, but I decided not to think too much about it, and to focus instead on what I was going to wear for him. I chose a bra-and-panty set that I had bought especially for such an occasion, if it ever arrived. The bra was made of red lace, the cups sitting low enough on my breasts to show part of my nipples, while the G-string was not much more than a string of pearls that were supposed to sit between my pussy lips.
I slipped the G-string on and immediately found myself getting turned on by the cool pearls rubbing themselves against my clit, as well as my slit and ass. When I had bought the set a few months earlier, I hadn’t even let myself try it on I wanted to wait until someone else was going to take it off me, and now it was going to be my boss!
I decided to wear my favorite summer dress—a sexy black number that stopped at mid-thigh—and a pair of black heels that made me feel like a stripper. I was so nervous that it seemed to take forever to get ready, but I finally managed to get in my car “” after leaving my parents a note saying I was spending the night at my best friend Jill’s house “” and drive over to Tommy’s place. I knew there was no going back now, and that I was about to experience things I had only fantasized about. I could only hope that my nerves and inexperience wouldn’t ruin everything.
I walked up to Tommy’s front door and gave it a light knock. Tommy opened the door within a few seconds and stood in front of me, looking hotter than I had ever seen him. He was about an inch short of six feet tall and fairly muscular, with dark brown hair and the kind of hazel eyes that only about one in a million people have. I felt my legs start to shake as he invited me in.
“Thanks for coming, Allie,” he said, as if I had just shown up at his birthday party or something. He was so cool and calm that I felt completely awkward, with no idea what to do first.
He told me to make myself comfortable on the couch in the living room while he went into the kitchen. He came back out with two glasses of wine and sat next to me on the couch. “Nothing has to happen if you don’t want it to, Allie,” he assured me, and handed me a glass.
We clinked our glasses together and each took a sip, mine much larger than his. All I could think of was how different he seemed now from when he was at work, and I let out a little giggle as I recalled how he had reprimanded me one day for being late.
“What’s so funny?” he asked, and I reminded him of how he’d scolded me the week before. “And that’s funny?” he asked, with a grin on his face.
Feeling bold now, I said, “No. What’s funny is how I told a couple of the girls at work that I wished you had spanked me instead.” I felt myself blush at that point, but I didn’t care anymore all I could think about was how amazing it was to be with him like this.
He raised his eyebrows. “Do you like it when I scold you, Allie?” he murmured. “How about when I boss you around?” I took another sip of my wine and just made a little sound in my throat for reply. “I’m sorry, I didn’t hear you, Allie. Speak louder, please,” he instructed.
I could already feel the warmth starting between my legs. “Yes, Tommy,’ I told him. “I like it when you boss me around.”
“Good,” he said, “now I want you to show me your tits. Very slowly. I want you to put on a nice little show for me.”
My dress was the kind that I could slide right off my shoulders and push down. I did that now, slowly letting the fabric reveal my skin, and I went even slower when I got near my tits. I watched as Tommy followed my dress with his eyes, and I could see he was pleased when I exposed my lace-covered breasts. The top of my areolae were visible over the top of the bra, and my nipples were so hard they were trying to poke through the lace that shielded them from his sight.
I stopped with the dress just below my breasts, and watched as Tommy took in my firm mounds. “Very nice, Allie,” he said. “You’re very good at doing what you’re told. Now why don’t you peel your bra down past those nipples and let me see what they look like.”
Again I did as he instructed, and exposed my nipples to him. My breasts are a C-cup and very firm, and my nipples are dark pink and very thick, almost like pencil erasers. Tommy seemed to like them all right, and he reached out to touch them as they became visible. “Wow, Allie, your tits are fucking amazing!” he exclaimed. “Has no one ever touched them before?”
“Just me,” I replied, which was totally true. I sat there with my bra hanging below my tits and watched as my boss rubbed my nipples between his fingers. After a few minutes of playing with them, he suddenly directed me to straddle his lap. I climbed on top of him, with my dress still half on, and faced him.
“I want these right in front of me so I can see what I’m doing to them as closely as possible,” he said. He continued to rub my nipples, squeezing them lightly from time to time, and making me very horny in the process. I started to rub my pussy against his crotch, and I could feel his cock growing underneath me. “Does this feel good, Allie?” he asked. “Do you like it when I squeeze your nipples?”
“Yes,” I moaned. “It feels incredible.” After all those years of playing with my own tits, it felt so much better to have someone else doing it for me. Then he pulled me toward him, lifted my breasts from underneath and raised one of my nipples to his mouth. I thought I would come right then and there. I looked down and watched as his mouth started sucking on my nipple, gently tugging on it with his teeth. He alternated between my breasts, sucking on each of them equally. I could feel how moist my pussy was, and I was getting really turned on, feeling the pearls of my G-string rubbing over my clit. I knew I would come if I kept gyrating on Tommy’s lap while he sucked on my tits.
Now his hands went underneath my dress and he grabbed my ass cheeks, grinding me harder against him. My nipples were hard and throbbing from all the sucking, and I was right on the brink of coming when Tommy suddenly stopped.
“Of all the things I’m going to teach you tonight,” he told me, “this one might be the most important.”
“What?” I whimpered, thinking I had done something wrong.
“How to delay someone’s orgasm, so that when you finally do let them come, it’s the most unbelievable feeling they’ve ever had,” he answered.
Holy shit, I thought, this was going to be even better than I expected! He then told me to take the rest of my dress off, along with my bra. I stood up and did as I was told, leaving me in only my pearl G-string.
“Would you like to learn how to give a blowjob next, Allie?” Tommy asked.
I was so eager to learn how to suck dick that I didn’t even care that my pussy felt like it was going to explode. “Yes,” I said, “I’ll do anything to learn.”
“Well, all you have to do is kneel in front of me and put my cock in your mouth,” he said. I knelt in front of him as he unzipped his pants and took his cock out for me. I had never even seen a real live cock before, and now I was about to put my mouth around one.
“I don’t know about other guys,” Tommy said, “but I like it when just the head of my cock gets sucked on first. Why don’t you start with just the head, Allie.” And with that he slipped his meat between my lips.
I sucked on his helmet and really enjoyed the taste of his precome. I licked and sucked on the head of his cock until he told me I could take some more of his manhood in my mouth. I swallowed another inch of him, and then a couple more, until I was about halfway down his shaft. His cock was very long and pretty thick, and I wasn’t sure if I was going to be able to take in all of it. Tommy kept telling me what a great job I was doing as he reached down and cupped my breasts, rubbing my very sensitive nipples between his fingers. I really loved sucking his cock, and kept trying very hard to get all the way down to the base of it.
When his cock was almost touching the back of my throat, he told me that it might take a few more lessons for me to be able to deep-throat him. I nodded my head in agreement while still sucking on his amazing piece of meat, never wanting it to leave my mouth. But that wish wasn’t granted, as he informed me that I had done such a great job sucking dick that it was now time to move on to a new lesson. I reluctantly let him slide his cock out of my mouth as he got up and led me to his bedroom.
He told me to lie on his bed on my back, and to close my eyes. I did so, and heard him removing his clothes and letting them drop to the floor. I kept my eyes closed the entire time, even though I was dying to see him naked. I almost opened them when I heard him take something out of a drawer, but I squeezed them shut, wanting to be a good student. Then I felt him kneel next to me on the bed as he lifted my head up and tied something around it, covering my eyes. A blindfold!
“I want you to concentrate on the feeling of what I’m doing to you,” he whispered in my ear. Then I felt him move down to the foot of the bed, and felt his hands on my legs as he spread them open. I still wore my G-string, and he said something about how hot it was to see the pearls covered in my wetness. He started moving the string of pearls so that they rubbed against my clit and pussy hole, further drenching them in my juices. I was moaning and groaning with each touch on my clit, and I was really happy that I had decided to wear that particular G-string.
Not being able to see really heightened my senses, and I almost jumped when I felt his breath on my pussy. Tommy told me to relax, and assured me that I was going to love what he was about to do to my cunt. And he was so right!
The moment I felt his tongue on my pussy I knew I had picked the right person to teach me everything I needed to learn about sex. I honestly had never thought it would be this incredible! I lay there moaning as he licked my pussy, moving the pearls out of the way so he could get better access. He licked and sucked on my clit for a few minutes while he finger-fucked me, but then went back to feast on my entire pussy, sticking his tongue inside me as far as it would go. “You taste amazing, Allie,” he told me. “I don’t think I’ve ever eaten virgin pussy before.”
“Please don’t stop, Tommy,” I begged him, and he didn’t. He nibbled on my clit until I was about to come, then moved down to tongue-fuck my opening again. He continued doing this until I wanted to come so badly that I was begging him to let me explode all over his face. I was writhing around and trying to rub myself into his mouth so that I could have my first orgasm with a man. He was driving me crazy with his tongue, his lips and his teeth. I wasn’t sure how much longer I could last when he told me to grab my tits and play with them for him, and he would finally let me come.
My hands went immediately to my tits and I pinched my nipples between my fingers, trying to give him a good show. I could tell from the sounds he was making that he was enjoying it. My body rocked back and forth as I squeezed my nipples harder, and he continued to devour my cunt as I finally came, drenching his masterful tongue with my juices, screaming and moaning so loud that I was sure I would wake his neighbors.
“Now for your final lesson,” Tommy said. He removed my blindfold as he positioned himself between my legs. “Are you ready for this, Allie?” he asked.
“Oh God, yes!” I panted, and with that he slid his cock inside me as far as it would go and took my virginity.
Finally I had a cock inside me! And Tommy fucked me so good, alternating between being slow and gentle and fucking me so hard that my tits shook up and down. He fucked me missionary-style, doggie-style and on our sides, and finally he guided his cock inside me as I straddled him. It felt amazing to be on top of him as he reached up to play with my tits. I even had another orgasm while I was riding him.
I never wanted to stop fucking him, and I continued bucking up and down on his cock until he flipped me over on my back and found my opening again. This time he thrust so hard and moaned so loudly that I knew he was about to come. “Your pussy is going to make me come, Allie,” he grunted. “Are you ready for it?”
“Yes!” I screamed. “I’m dying to have your come inside me!” We fucked as hard as we could for about 20 more seconds until he finally unloaded himself in my pussy.
We collapsed, completely exhausted, and slept for several hours. When we woke up we repeated what we had just done, and we continued to fuck for the rest of the summer. And that fall, when I went back to school, I found I didn’t have any more trouble with the opposite sex. I guess all I needed was to get the awkwardness out of my system. And I owe it all to Tommy—the best boss a girl has ever had!
