From Virgin To Stud My Evolution

In the summer between my Freshman and Sophomore college years I lost my virginity. I know, a little later than most. But I was an exceedingly shy guy. In high school I was fairly short and wore thick glasses. And a nerd, great at math, not so good with girls. I put on some additional height my last year of high school and first year of college. Also got rid of the glasses. Improvements to be sure but I was still painfully shy.

I worked a summer job as a helper with an HVAC company. The lead tech guy took me on service calls, teaching me the basics. My world changed on one assignment.

Bill, my boss, said we had to do an annual maintenance check at this gal's house. "Let me tell you, she's a real looker. Too old for you but just right for me," he said with a laugh. She was indeed a beautiful, sexy woman, probably mid-thirties. Bill and I went about our business and finished up in about an hour. "Would you guys like some ice tea," Melinda asked. Bill lost no time in accepting. "Who's your new guy?" "This is Tom. He's working for us this summer."

"Bet you got girls hanging all around you," she directed her attention to me. "Not really," I stammered.

We finished our drinks and headed back to the shop.

******

"Tom, you remember that annual check we did Monday. You know, the good looking gal?"

"Yeah, the one you liked."

"Little it did for me. Anyway she says the furnace is making a vibration and wants it checked out. She asked for you."

"Me? Why me?"

"Beats me. I offered to go but she insisted on you. Maybe after your hot bod."

"Yeah, sure. OK, when do you want me to go?"

"She said this afternoon, after 3. Then you can go home after you finish."

Melinda met me at the door. "Thanks for coming, Tom. It's really not much of a problem but since I just paid for the maintenance I wanted it checked out."

I turned on the blower and could hear a rattle from the furnace in the basement. A glass was sitting on the furnace top. I picked up the glass and the rattle went away. "Silly me, I guess I left it there after you guys had your drinks. Now that you're here, stay for a few minutes. Tell me about yourself," as she fixed two ice teas.

We sipped our drinks as I told my life history. What little there was.

"I need a few things fixed around here. Loose cabinet knobs, that sort of thing. Would you like to do some work for me? When you're not working at the HVAC place?"

"I suppose but it would have to be on Saturdays. I do things with my family on Sunday. How much would you pay?"

"I think maybe $15 per hour. Does that sound ok?"

"Yeah, that's about what I make at the company. The extra money would come in handy. I'm saving up for a better car. Mine is on its last legs."

"Great. How about you come over this Saturday, say 10 AM and I'll make up a list of stuff to do. Figure on being here most of the day. My husband's tools are still here. You can use what you need."

Melisa had me do a bunch of minor handy-man type projects. Along the way we chatted. I wasn't tongue-tied, perhaps because she was quite a bit older than me. And she had an easy-going manner. She asked me to plan on doing more next Saturday.

Saturday I was back, doing some repairs on patio furniture. The sun was warm and by mid-afternoon I was sweating. "You seem really hot, Tom. Come over here in the shade and have some ice tea. We can chat."

Melisa was married for fourteen years and currently separated. Her husband now lives in another city and they would likely be getting a divorce. Things just didn't work out. "It was my fault. He was a good guy but just not too good in bed. I love sex. Good sex. So I found other guys to help out. He knew I was playing around but turned a blind eye for a while. But it ended when he came home and found me with two guys in our bed.

"Tell me about your girlfriend. Or do you have more than one?"

"I don't have one. Somehow I have never met anyone who liked me that way."

"You're still a virgin? How old are you?"

I blushed and nodded. "Nineteen".

"Honey, let me tell you. You are a very good looking guy. Any girl that passes you by is a fool. You're not gay are you?" "No!" I replied indignantly.

"It's a hot day. You know, we can use the pool. My husband left behind some clothes when he moved out. I was about to toss them out. Let me check if his swim suits are still here."

She came back with one pair, similar to a speedo type. "He took all of his trunks but there was this. I doubt it fit him anymore but it might fit you. You can change in the cabana over there. I'll go inside and put on my suit." The suit was a tight fit. Maybe it had shrunk or maybe her husband was smaller than me. I had an embarrassing bulge.

"What are you doing in there?" Melisa called to me. "Come on out." Well, here goes, I thought, as I exited the cabana with a very red face. "Oh, my, Tom. You are quite the hunk! If my husband had looked like that I would have stayed married to him. Come over here."

I was both mortified and proud. I had a big cock that barely fit in the tight suit. I stood red-faced in front of Melisa. "Turn around, Tom. I want to see your butt. Very nice, tight buns. Now turn back to me," as I stared at the tiny suit she had put on. Very sexy!

Melisa stood up and placed a hand on my crotch, which made my cock start to grow. It was becoming very uncomfortable in the tight suit. "Poor baby, am I making matters worse? Here, let me fix it," as she pulled the front of my suit down over my cock and balls.

"God, Tom, you have a beautiful cock. Pull the suit down the rest of the way. How big does it get?" "About 8 or 9 inches, I guess." Actually I had measured it many times. It was 8 ¾" and about 6 ½" in circumference. I now was standing proud in front of Melisa. She took my cock in her hand and stroked it, bringing it to full size.

Melisa pulled me over to the chaise lounge. "Stretch out here, I want to suck your cock." Picture this: Shy me, a virgin, getting my cock sucked by a good looking older woman in a tiny bikini. Not that I had anything to compare it to but she sure knew what to do. I lasted only three or four minutes before shooting off into her mouth.

"Honey, what a load. You must have been saving it up for a long time. Was that your first blow job?" "Yes. It felt wonderful. Thanks so much. I was going to warn you I was going to come but everything happened so fast."

"Don't worry. I love to suck cock and always swallow. You have the best cock I have ever played with. And so much cum.

"I'd like to have more fun with you, but I have to get ready for a dinner date. Come next Saturday and we can do more. OK?"

Saturday took forever. "Hi, Tom. I have some work for you to do. Ready to get started?" Not what I was expecting and I must have looked disappointed. "Poor boy, don't worry. You have just the tool for this work." She took me by the hand and led me to her bedroom.

"I want you to fuck me. I know it's your first time so I'll tell you what I like."

She peeled off her bikini and stretched out on the bed. I had never seen a nude woman before and couldn't help staring. I quickly pulled my clothes off, my cock popping up. "Lay down beside me," she directed as she reached down for my cock. "Oh, this is going to be fun. You have the biggest, hardest cock I have ever handled. Baby, it's really going to fill up my pussy."

She took my hand and moved it to her pussy. "Feel around, Tom. Explore my pussy. Take a finger and put it between the lips. Now slide it up and down. Good. Good. Now find my pussy hole. Yes, there. Push your finger in, slowly. Now use your finger like a little cock. Fuck me with your finger. Very good. Feel how wet I'm getting." While I was finger-fucking my first pussy, Melisa was stroking my cock. My cock was leaking pre-cum and she spread it around my cock head.

"OK, Tom, get between my legs. She took my cock and positioned it between her lips, moving it up and down the slit. "Feels good, doesn't it?" "Feels great." "OK, you do it the same way. Up and down." "Feel where my pussy hole is. Yes, there. Push your cock head in. Stop. Just the head. Now back out. In again. Keep doing that."

"Melisa, I'm going to come. Oh, damn, here it comes," as I spurted between her lips. I was so embarrassed. I didn't even get my cock inside. What a loser, I thought.

"That was a good first time, Tom. Most guys would just shove it in. You had remarkable restraint," she consoled me. "Come on, let's get a drink and in a few minutes we can do more."

She pulled me out of bed and led me, nude, to the pool-side bar. "How about a rum and coke?' "Sure, fine."

We stood by the little bar sipping the drinks. Melisa was older but in really good shape.

Apparently reading my thoughts she explained: "I'm 35 and work hard to keep my figure. I run three miles a day and work out in my gym. I look pretty good, don't I?" "You look terrific."

"Do you like my breasts? Not as big as many other women. But they're still perky," she fished for a complement. "Would you like to touch them?

"Oops, cold hands! Go ahead, massage them. Now play with the nipples."

I had almost forgotten I was nude until she called my attention to my rising cock. "See, I told you we would have more fun." A few minutes later with my cock at full measure we went back to bed.

"OK, Tom. First I want you to rub your cock up and down my slit, like before. Yes. Now find my pussy hole and push in your cock head. Good. Now back out. And in. Now push in a little deeper. Now back out. Keep going, you're doing fine."

She reached down and felt my cock. "You're only half way in and already filling me up. OK, push. Oh, baby, you have the greatest cock. Now pull almost out, now back in, deep. Keep going."

A few minutes later I could feel the pressure growing. "I'm getting close!" Melisa moaned and grabbed my ass cheeks, pulling me into her. I felt her pussy muscles twitching and gripping my cock, causing me to explode. I stayed in her for another minute until I felt my cock shrink.

I hoped I hadn't come too soon. "Tom, that was terrific! I doubt any guy has done better his first time," Melisa said. "You made me come! Congratulations." After taking a shower together we sat by the pool and sipped another drink. "Tom, I told you I like sex. I got an early start.

"I adored my two older brothers. They said I could be their girlfriend when I grew up. Later I came to realize how good looking and sexy they were. The day after my eighteenth birthday they seduced me. I wanted it too. Almost every night one or the other, sometimes both, would come into my bedroom and fuck me. I loved being their girlfriend and loved what we did together.

"I'm pretty sure mom knew something was going on. She took me to our doctor for birth control pills. I'm sure glad she did.

"My brothers taught me to suck cock. They pumped out lots of cum. To this day I love having a hard cock spurt into my mouth. A few months after we started they took me to a party. That night six guys fucked me. I loved the attention and I loved the sex. But mostly my brothers kept me to themselves. Maybe they were worried since we were siblings.

"More likely they just wanted a ready fuck. Needless to say I became very proficient in satisfying them. We did all kinds of positions. They would double-team me. One in my mouth, one in my pussy. Their cocks were good size but smaller than yours. With some difficulty I could take them in my ass. Never really cared for ass fucking. But I did like it when one was in my ass and one in my pussy.

"They also liked to play with each other. I liked to watch.

"A year later my brothers left, one back to college, the other to take a job in Chicago. I started dating and became real popular with the guys, as you can imagine. But I got tired of breaking in new guys. Tired of their fumbling around, quick releases. Present company excepted. The worst was the bragging afterwards to their friends. Not you, I hope."

"No way."

"Good. Anyway now I was in college. Older guys knew more and were better at it. I settled down mostly to one guy at a time. I also started worrying about my reputation and became much more discrete. In my senior year I met a guy that had long term possibilities. Good looking, smart. And his family had money. Lots of it.

"We dated through my senior year and got married after graduation. His parents set us up in this house. Bill started as a junior executive in his father's business. I'm not sure I was in love with him but he was a really good catch. Too bad he wasn't very good in bed.

"I soon got bored and started playing around. He found out. For financial reasons we haven't gotten a divorce but he moved out two years ago.

"So that's my story."

By comparison my sex life could be summarized in two words: jerking off.

The next Saturday Melisa took me shopping for some clothes. She said I needed a better wardrobe. Next we went to lunch and she coached me on ordering in a nice restaurant. Then back to her house for sex, which was great. Later we went out to dinner, again with coaching on proper etiquette in a fancy restaurant. All part, she said, to round me out as a stud.

The next Saturday we headed to the mall to do some more shopping. "Tom, I know you're a shy guy. Probably the hardest thing for you is starting a conversation with someone. Am I right?" "Yeah, I don't know what to say, so I usually don't say anything."

"Well, the trick is to pick out something that a person has or is doing. It can be almost anything. And then comment to that person. Here, let's get in line to checkout. See the woman in front of us. What might you say to her?"

"Hum, I don't know. What?"

"Well she has some balloons and some other party stuff. Maybe a birthday. How about, 'Looks like someone's going to a birthday party'? Go on, try it when we get there."

"Looks like someone's having a birthday party," I said to the woman as we waited in line.

"Yes, my daughter. She's going to be ten tomorrow," she responded with a big smile.

"Going to have lots of friends over?" I adlibbed.

"Too many," she said with a laugh. "Well, hope she has a good time." "Thank you."

As we walked away from the checkout, Melisa said "see, you didn't know that woman from Adam but you created a conversation. Now just imagine she was some sweet young thing buying the same type items. Would have worked just as well.

"Let's go into this store. I see some girls more your age. OK, see the one looking at shirts? Go over there and ask her something. Maybe which shirt you should buy."

I walked over to the shirt rack and pulled two shirts from the rack and then glanced at the girl now standing beside me. "Which of these two colors do you like better," I asked. She looked at me, smiled, and said "I like the blue one. For you?" "Yes." "Then I would get the red." she offered with a brilliant smile. I thank her as I put the blue shirt back on the rack.

As we left the Mall, I thanked her for her suggestions. "I'll work on it," I promised. "You'll do fine. Now let's head home, I'm horny."

Every Saturday was a new adventure. Melisa showed me various positions. My first time was missionary position. Then we switched to doggy which we both like better. Next she climbed on top and fucked me both cowgirl and reverse cowgirl. I found it more difficult to come with those positions. We fucked in the shower and with her bent over the kitchen table. We fucked on the pool deck. We did a lot of fucking.

"Honey, you ready for some graduate studies?"

"Oh, and what does that mean?"

"You'll see," as she teased me.

Like most Saturdays together we started in the shower, fooling around and doing a little fucking. Moving to the bed I licked down her body and made love to her pussy with my tongue. I had learned what she liked and she came in a few minutes.

She turned over and I rubbed my cock head up and down her pussy lips and then gradually slid into her warm tunnel. We leisurely fucked for at least ten minutes before we both came.

"That was so nice, Tom. You have become a very sensitive lover. I just love how you make me feel."

She reached down and massaged my wilting cock. "Now I want you to do something else. Please eat my pussy again."

"Now?" "Yes, I want you to do this for me. You've tasted your cum before when we kissed after I sucked you."

I wasn't sure that I wanted to do this but would give it a try. Scooting down between her legs I spread her lips apart with my fingers. Her pussy was glistening with our combined juices. With further encouragement from Melisa I stuck my tongue between her lips.

It tasted ok, not really much different than when I ate her out. I continued licking up and down her slit. She pulled her lips apart so I could go deeper. Still tasted ok.

"Tom, I'm going to push out some of your cum. There, see it?" Creamy white cum oozed from her pussy hole. "Taste it, Tom. Come on."

Using the tip of my tongue I lapped away. She pushed more into my mouth.

Suddenly she pulled my head into her crotch, mashing my mouth on her pussy. "Oh ..... Oh .... Oh God. So good! So good!" she exclaimed as she climaxed. She released my head and slumped in the bed.

"Tom, that was the absolute best I have ever experienced. I can't thank you enough. Thank you for doing it. Was it ok?"

"Yeah, I guess. Not quite what I expected but if you really like it, that's ok."

Eating what she called creampie became a regular addition to our love making. I was proud of my growing skill. Melisa told me I would have plenty of girls in my bed. I hoped so.

*****

The next adventure came two weeks later.

"Tom, I told you that way back when my brothers fucked me. They liked to do anal and I went along but it really wasn't my thing. Most women don't care for it either. Our nerves are in our pussies and clits. But guys are different."

"How so?"

"Gay bottoms like to be fucked in the ass because it feels good. Guys have prostates. It's situated in front of the rectum. If it is massaged, say by a guy sticking his cock in, it can feel really good. Turn over and let me demonstrate."

Melisa pushed a lubricated finger into my butt. "How's that feel?"

"OK, a little weird, but ok."

"Now I'm going to find your prostate," as she replaced her little finger with her index finger. "There, can you feel what I'm doing?"

"Yeah, it's making me horny." Melisa reached in front and massaged my growing cock as she rubbed my prostate with her finger. "Melisa, that's going to make me come," I warned moments before I squirted into her hand.

"Wow, that happened so fast. Just because you massaged my prostate."

"Ask any guy bottom. They'll tell you. What do you think?"

"Well, it did make me come. But it happened so fast, not like the slow steady buildup when we fuck. I like fucking you much better."

We moved to the pool, still nude. Fortunately, Melisa's house was secluded with a high fence.

"Well, Tom, how does it feel to be fucked in the ass?"

"What do you mean?"

"It may have only been my finger, but it could have been a skinny cock. Would have done the same thing. Except you might have felt cum squirt into you."

"Quit teasing me, Melisa. You should know by now that I'm not gay."

"Well, I'm trying to make a point. Sex should be fun. Most straight guys won't let a woman touch their ass. It's a guy thing. Even if it were to feel good. And yet I gave you a climax. Using just my finger. You're a good sport and willing to try stuff."

We went out for an early dinner. Back at her place we had rum and cokes and talked some more. "Here's what I want to do," Melisa started. "I have a small dildo which I'm going to slide into your ass. Not much bigger than my finger and I guarantee it won't hurt. After you loosen up I'll put in a butt-plug."

"What's that?"