From Virgin to Stud, My Evolution

It's a rubbery dildo that has ridges and is made so it will stay in. It will massage your prostate like my finger did. Then you are going to fuck me. The sensations from our fucking plus the prostate massage should give you a mind-blowing climax. Want to try it?"

"I don't know. That sounds really weird."

"Come on, Tom. I did it to one guy I used to date. He said it was the most intense sex he had ever had."

Another rum and coke and I was persuaded to give it a try. Melisa slowly penetrated me with the little dildo. "Feel ok, Tom?" "Yeah, about like your finger but tighter."

She stroked the dildo in and out for several minutes. "OK, let's try the butt-plug."

The ridges were bigger than the dildo and Melisa had to gradually work it into my ass. "There, it's in all the way. You doing ok?"

"I guess. Feels really weird, like I need to take a crap. But it doesn't hurt. Now what?"

"Turn over, I'm going to suck your cock. When it's hard you fuck me."

I pushed my cock into her doggy style. With each thrust I could feel the butt plug move slightly in and out, rubbing my prostate. Within only a few minutes I exploded into Melisa. I rolled off and collapsed.

"Oh, boy, that must have been good. You haven't come so quickly or hard since your first time. Now eat my pussy. Eat your creampie."

"Give me a minute. I need to catch my breath."

Later we talked.

"Where did you ever get the idea about butt-plugs?"

"From watching my brothers. They had a lot of fun together.

"Tom, most women would be shocked about creampie eating and prostate massaging. Far too exotic and beyond anything they have ever experienced. But I can guarantee you that those who aren't put-off will be most exciting lovers. You are something special. Great body, great cock, great personality, and now great experience. Probably more experience than any other 20-yr old around.

"Your summer tutorial is almost over. Time for you to think about school. And those cute girls. But remember, don't scare the wits out of some sweet, inexperienced girl. Anyway, that's my advice to you.

"But we still have next Saturday. Save up all that cum, don't jerk off, and we will spend the day in bed."

Melisa made it clear our fun was over. She said I needed to date girls my age. I parted with deep regret and thanks. I was still fundamentally a pretty shy guy but at least I knew I could perform if given the chance.

******

During my college sophomore year I practiced making small talk with people like Melisa showed me. It worked pretty good. I used to be tongue-tied, searching for a clever introduction. Now I looked for something, almost anything, that could be a topic. My confidence in social situations was slowly improving.

I met and dated several girls in my classes. I didn't try to push any of them into bed and by end of the school year had sex with only two. Jill was the very first girl my age I fucked. She currently had two guys she regularly saw but wanted to give me a try. Her sexual experiences, although somewhat extensive, were rather mundane from my new perspective. A warm-up blowjob and missionary position. Over the next several months I added doggy position and pussy eating. She loved both and thought I was the greatest.

The second girl, Nancy, lost her virginity to her long-time boyfriend last summer. He now attended another university 800 miles away. She missed him and was saving herself. It took several platonic dates before I bedded her. She was short on experience but exciting in bed. I showed her how to properly suck cock. She loved my pussy eating. I didn't feel pressured to perform which added to my enjoyment. She planned to reconnect with her boyfriend at spring break. His gain, my loss.

I had even more fun my last two years of college. Jill had put out the word in her sorority that I was really good in bed. I was invited to all their parties and almost never failed to hook up. The girls loved that I ate their pussies. Many girls said their guys wouldn't go down on them. Or if they did, for just a minute or two as warmup. I was the only one who would bring them to climax with just my tongue.

One time I went for it and ate my creampie, the first time since Melisa. The girl thrashed around, mashed my mouth to her pussy, and very forcibly came. We hooked up several more times. I was pretty sure she told her girlfriends.

I worried about what others would think. Eating creampie is not common and some girls might think it's a gay thing. Eventually I decided that an experienced tongue was as important as a decent cock.

One girl was rather aggressive in getting me into bed. Her name was Carol. "Tom, I love sex and like lots of different cocks. You fucked one of my friends. She told me you have a big cock and know how to use it." I anticipated a really good time but was disappointed in her passiveness. I worked hard with my tongue and cock and was unable to bring her to climax.

"Thanks, Tom. That was fun." I was surprised since I considered our sex a failure. But not wanting to disappoint we met again that weekend. We showered together and I briefly fucked her before moving to the bed. Using my tongue as expertly as I could I ate her pussy. She seemed to enjoy it but still didn't climaxed. She was very passive.

I was about to mount her doggy style when I had an idea: Let her ride me. I laid down and pulled her on top, facing me. "Grab my cock and push it into your pussy." She started to rock up and down and I added to the motion, my cock doing long strokes. She picked up the rhythm.

"Oh God. Oh." She mashed down on me and climaxed. "Thank you, thank you, thank you," she exclaimed as she enveloped my cock with her slippery pussy. "That was my very first climax. I didn't think I could ever have one. Thank you. That was wonderful!"

Other than providing a stiff cock I had contributed very little but was nonetheless very pleased for her. A couple of days later I ate her pussy to climax and then she again successfully rode me cowgirl style. Carol went on to date some guy in her class. She later confided that she now was having regular climaxes.

I bedded about a dozen girls during college. If some other guys could be believed that was only a modest total. But I tried to satisfy each one as I became more aware of the nuances of love-making.

*****

Upon graduation I took a job as a junior data analyst at a large media company. The guys in my group took me out for drinks as a welcome.

"Have you met Mary yet?" one of the guys asked. The others laughed. "No, whose she?"

"Mary works the next level up. She makes a point of meeting all the new guys."

"Yeah, she's quite a fox," another guy added with a laugh. "Most of us have 'met' her."

I said I didn't understand.

"Mary fucks every new guy that's hired unless he's downright ugly or gay. Your time is coming. Oh, maybe sooner than you think," he added as a slender brunette approached our table.

"You're the new guy? What's your name?" "Tom, Tom Randall."

"Nice to meet you, Tom. My name's Mary Miller. I work in Production."

"Come join me at my table over there so we can talk," as she took my hand. I looked back at the guys and they gave me thumbs up.

Mary asked me what school I went to and if I had a girlfriend. In turn she gave me a short version of herself: single, 23 years old, hired two years ago.

"What did the guys tell you about me?" "Not much, just that you worked one floor up and were good looking."

"Did they tell you I check out all the new guys? You're good looking. How about us having some fun together."

"Fun, like sex?" "Yeah, you're not gay or something?" "Nope. When?" "How about now. We can go to my place."

I had responded with confidence but deep down wondered if I would be good enough. This girl had been around. The word would probably be out if I performed poorly. I needed to try my very best.

Half an hour later we were in bed together. "Oh, honey, that's a man-sized cock you got there. I sure hope you know how to use it. You ready?"

"Yeah, but we have time. How about I eat your pussy first?" "Go for it, stud."

I drew upon all my experiences to bring her to a strong climax after some ten minutes of muff diving. Not missing a beat, I asked her to roll over onto her tummy. Positioning my cock between her pussy lips I started rubbing up and down. Her pussy was dripping as I pushed the head in and then pulled back out, in and out, just using the head.

"God, that feels so good. Shove that big cock into me."

On the next stroke I penetrated half way and then bottomed out.

"Oh, baby, your cock is so big. Filling me up. Fuck me."

I set up a steady thrusting and reached under her to play with her clitoris. I was getting close but was trying to time my release with hers. She beat me by half a minute. Her pussy was gaping as I pulled out my cock.

"Damn, Tom, you're really good. You have a magic tongue and a huge cock. And you know how to use it. Thanks. It was great."

"Oh, we're not done yet," I responded. "Is your cock already recovered?" she asked with incredibility as she reached for my cock.

"No, a few more minutes. But my tongue is ready." "What do you mean?"

"I'm going to eat your pussy again. Creampie and all. Spread your legs."

Her engorged pussy was still gaping from my cock. I decided a freshly fucked pussy is the sexiest thing in the world. I touched her lips with the tip of my tongue.

"God, you're something else. No one has ever done that to me. One of my girlfriends asked her guy to do it but he refused. OK, if that's what you want. Go to it."

I lapped away for some ten minutes and she used her pussy muscles to squeeze out my cum. "Show me. Show me your tongue," she implored. I stuck out my tongue covered with cum and then swallowed.

"I have never met anyone like you. Would you like to fuck me again?" she asked as she fondled my still limp cock. "Come up here and let me suck it. Now we both have tasted your cum."

A few minutes later she mounted me and we had a leisurely fuck.

"Tom, where did you ever learn to satisfy a woman like that?"

I explained that I was a very shy virgin of twenty when I met an older woman who taught me how to make love. Mary continued to praise my performance.

"This is a one-time thing, Tom. But after I spread the word you will have plenty of pussy.

I had passed the test!

Mary was true to her word. The next day a cute blond stopped by and introduced herself. Over the next week two more girls said hello. The guys in my group decided my test run with Mary must have gone well. Very well.

I had a few dates. But in spite of the romantic opportunities I needed to concentrate on my new job. I had high goals and needed to make my mark as quickly as possible. The guys in my group helped with insights as to the company's personality and the key people in various departments. My boss assigned me to a project team with members from several areas. It was his way of giving me exposure.

*****

A couple of months later I was assigned to another work group. One of the members was a really good looking gal, a bit older than me but well put together. One afternoon after the others had left for home she made her intentions clear. She wanted sex with me. She said she was married but liked to play around. I later learned Mary was her good friend.

I was concerned about mixing sex and work in such close proximity. Lois was persistent and I realized saying no would create as many problems as saying yes. We got together the next Friday after work.

Shes was insatiable. We started fucking in the shower. Then moved to the bed whereupon she devoured my cock. I hadn't had too many blowjobs and no deep throats. Lois knew how. Her throat gripped my cock like a warm glove. I only last a few minutes before pumping my load directly down her throat. This girl could sure suck cock.

I barely recovered before she pushed me down to her crotch. "Mary says you eat pussy like a champ. Show me."

I tried my very best. She had a beautiful pussy that was already leaking. After using my tongue I fucked her with two fingers and massaged her clit with my tongue. Then back to tongue fucking. I alternated for several minutes until she pulled my head into her crotch and came with a shudder.

"Really good, Tom. Mary said you were the best. I agree. How soon before your cock is ready again?"

"Maybe 20 or 30 minutes, maybe less if you play with it. She played and sucked and finally my cock showed some life. It wasn't completely hard when she told me to stick it. I held it for the first couple of minutes to keep it from bending as it pushed into her pussy. We fucked doggy style for some minutes and then she mounted me reverse cowgirl style.

She was the most aggressive lover I ever had. Then she sat down on my cock and used her pussy muscles to milk my cock. This was something new for me and felt terrific. Another minute and I blasted a big load deep into her pussy.

She immediately turned around and planted her gaping pussy on my mouth. I licked and probed and sucked as she squirmed above me. I was almost smothered by her pussy. My cum was dripping into my mouth. She came with a series of moans and rolled off me, panting.

"God, that was great," she exclaimed. "Mary said you would do a creampie. Thanks. You're a good sport."

We showered together and went out to dinner. I was ready to go back and fuck some more but she said she needed to get home. Her husband would be expecting her.

"Tom, have you ever been in a threesome?" "No. What do you mean?"

"Once before my husband and I invited another guy into our bed. I had the best time. Two guys eating and fucking me. Would you be interested?"

"I don't think so. When I think of a threesome I think of two girls and a guy. I wouldn't be comfortable with another guy."

"Well, think about it. My husband is not gay and there would not be any guy-guy stuff. Just two guys fucking the hell out of me."

Monday the team was back at work. Lois gave me a big smile when I arrived but otherwise no indication of our heated Friday fun.

Settling into my job I tried to reassess my sexual experiences. Thanks to Melisa's efforts and my subsequent efforts getting sex was becoming easier. I decided, however, that I had to keep a low profile. If management saw me as a party animal my opportunities for advance would be limited. Unlike some of my coworkers I never spoke of my sex life other than in the most general terms. Who I was dating and what we did was not anyone's business. The guys did know that Mary said I was great in bed. I was surprised to learn that my reticence added to my perceived attractiveness.

Meanwhile behind the scenes I had plenty of dates.

*****

A year went by and I received a small promotion with the department. I was regularly dating two girls with several others from time to time. Lois snagged me a couple of times. She said her husband and she were throwing a party in two weeks. Mostly people from work. Would I come? I agreed but reiterated my reluctance to a three-way.

It was a great party. They had a DJ and two bars set up. A local BBQ joint catered. Almost everyone from the group came plus another 30 or 40. Midway through the afternoon Lois hugged me and planted a big kiss on my lips. "Hey, stud. I hope you can stay later."

As the party wore down Lois's husband Greg came over. "Lois is hoping you will stay for a while. She said you really know how to fuck. I like to watch. And then join in."

I was taken aback by his candor. Well at least I knew what we did was no secret.

As the last guests were leaving Lois pulled me into the house. "Come with me. Greg will see the last people out and then join us." She led me to their bedroom and stripped. What a sexy body she was offering to me. I massaged her breasts as she felt the bulge in my pants.

"Take your clothes off," she hissed. "I'm so horny for you."

She spread her legs and I licked her dripping pussy. I heard the door open. Greg straddled her and put his cock into her mouth. She slurped away at his cock as I lapped her juices.

"Honey, I'm coming," her husband warned. "Come on, Greg, I want your cum." A moment later she clamped my head between her thighs and came with a shudder.

Her husband rolled to one side of her and I to the other. "Greg, you never come that fast. You must have been really excited. She reached down to stroke my stiff cock. "Look at Tom's cock. God, it's big. I'm sorry Greg, but it reaches places yours doesn't. Now I want him to fuck me."

She rolled onto her tummy and I positioned myself above. To my surprise Greg grabbed my cock and placed it at her pussy hole. I pushed and went balls deep in one thrust. Her pussy was gushing fluid. Greg lay beside us and watched my cock thrust in and out.

"Look at his big cock, honey. I can't believe how deep he is going. Oh, that feels so good."

I continued rhythmic thrusting for about ten minutes. We came virtually together and I rolled off, exhausted. Lois rolled over onto her back and spread her legs. "Now, honey. Come on, you said you would. Don't chicken out." Greg scooted between her legs and started licking her pussy.

"Good, Greg. Just that way. Oh, my, that feels so good." Greg lapped up my cum as she pushed it out. She thrashed around as she came with his tongue.

Afterwards Lois explained that she raved about my creampie eating and got his promise to do it. Several previous times he chickened out. "Greg, I'm so proud of you. That made me feel so good." As they cuddled together I put on my clothes and left.

Thanks for being a good sport," Lois said the next Monday at work. "I just loved having two cocks. And Greg finally ate a creampie. I've ask him to make it a regular part of our sexual fun. Maybe we could get together again soon. I have one more thing on my bucket-list: two cocks in me, ass and pussy. I know I can't get yours into my ass but Greg has done me a few times. Your cock in my pussy and his in my ass. Will you do it?"

"I don't know. Maybe you don't know but he took my cock and put it to your pussy."

"I was on my tummy and didn't see. Interesting. Did it really bother you that much?"

"Yeah, it did. It wasn't like he was playing with it. Just held it at your pussy and I pushed in."

"Greg was sharing my pussy with you. Maybe that was his way of showing you that it was ok to fuck me? Well, anyway, I had a great time. Thanks."

*****

The next Friday I was at the local bar and grill with my group buddies. Mary pulled me aside to talk.

"Tom, I have a favor to ask. My younger sister Janice is going to stay with me for a while. Trouble between our parents. Anyway I would like to introduce her to you. You're the nicest guy I know. She's very pretty and nineteen. Will you help me out?"

I wasn't sure about the match-making. Sounded like an extended blind-date. But I liked Mary and figured she wouldn't do something that would embarrass her sister. Mary arranged for us to meet and double date on Saturday.

Janice wasn't 'very pretty'. She was beautiful. Brunette like Mary, slender, nice boobs. I almost reverted back to my tongue-tied days but Mary kept the conversation going. The four of us went to a dinner show at a local playhouse. I couldn't keep my eyes off of her. I had never been in love but ...

I asked her out for the following Friday. Pizza and a movie. Nothing special except having this beautiful girl with me. Mary found her a job working at a local real estate company. I still was deeply involved with my studies. But we spent the weekends doing things together. I was pretty sure Janice was a virgin or at the least very inexperienced. I would have loved to take her to bed but was unsure how to create the moment.

"My sister told me you dated her."

"Yes, we went out once. I like her very much." "Just one time? Why?"