A Nice Guy Finishes First

Erin, Stephanie and I walked out of our class interested in the question posed by the professor – "Why do nice guy's finish last?" We were 2 months into our freshmen year at the community college in our home town. As we had tried to do all through high school, the three of us had taken the same class together. It was introductory Psychology. The professor was a middle aged lady who just liked to pose questions and get our response. The discussion for today was on the old idea of why women so often go after the "bad boys" while the "nice guys" get ignored.

I asked both of them who they would list as a nice guy. The same name came to all three of us – James Becker. He had been a friend to all three of us since Junior High. He was moderately cute, a decent athlete, pretty smart, always friendly and willing to help us out with our homework. As far as we could tell, he had never had a girlfriend in high school. He was just a little shy and seemed too afraid to approach girls for anything other than friendship. He was just very nice and never asked for anything in return for all he did for us. We came to the sad conclusion that we had pretty much taken advantage of him for years and never thought to return his kindness because he was just such a "nice guy."

Stephanie suddenly got this incredible smile. That smile had been known to produce instant hard-ons in many a guy. Well, maybe it wasn't just the smile – her blonde hair, 5' 8" trim figure with incredible D cup breasts and beautiful face may have had something to do with it. Erin and I had pretty much gotten used to the looks that always followed Stephanie. Anyways, Stephanie said, "I know exactly how we can repay James for all he's done for us. We will give him a night he will never forget! I think it is time we pushed our sexual boundaries a little farther and see how much fun the 3 of us can have with one guy!"

Over the next two weeks, we made our plans. We had the perfect opportunity to put them into action on a Friday night when my parents were going to be out of town and we would have my house all to ourselves.

About 6:30 that evening, I called James at his house. Between the 3 of us girls, I was probably the closest to James. I am pretty sure at one point in high school he had a crush on me, but was just too shy to do anything about it. While I am honest enough to admit I don't turn heads like Stephanie does, I think I am good looking too. My shoulder length hair is almost black and I have a great natural tan. I am about 5' 6" tall with a figure that has stayed in good shape from playing tennis on the high school and community college teams. I am especially proud of my breasts. While not as big as Stephanie's, I thought they were the perfect size and shape. Anyways, with my smoothest and most innocent voice, my words to James went something like this.

"Hey James, it's me, Wendy. Are you doing anything tonight? No, well Stephanie, Erin and I are at my house and we are having a slumber party since my parents are out of town. We have an assignment in our Psychology class we are working on and we really need a guy's input and perspective. Do you think you could come over and help us? You could, oh thanks. Um, now that I think about it, we aren't quite dressed right for guests. We are just doing the girl slumber party thing and lounging around in t-shirts and underwear. What, you don't mind? Well, I don't know if we would feel comfortable. Maybe, no never mind. Well, it's silly, but I was just thinking if you were dressed as casually as we were we would probably feel more comfortable. You don't mind? Ok, we will see you in a little bit wearing just your underwear and a t-shirt! Thanks James!"

When James arrived about 30 minutes later, we all met him at the door. We had each wanted the honor so we could see his face the first time he saw how we were dressed. We had done some planning to get just the effect we wanted. All 3 of us had on very skimpy thong bikini underwear that left very little uncovered. In addition, we had each picked a t-shirt that we felt would show our upper half in the best possible light.

Stephanie had on a white tank top made out of that stretchy mesh material. It was at least one size too small for her and covered her upper body like paint. The thin white material did not even begin to hide the dark aureoles and firm nipples showing beneath.

I had taken an old t-shirt and cut the bottom 2/3's off. It managed to cover my nipples, but a decent portion of the lower part of my breasts were showing where the t-shirt stopped. If I took too big a breath, the material would slip up to show a bit of the dark circle surrounding my nipples.

Erin had also taken the scissors to an old t-shirt. Erin is definitely what you would call petite. She is not quite 5' 2" with light brown hair and a body that was both slim and firm from years of gymnastics. While her breasts were smaller than mine, they fit her very nicely. She was wearing a loose t-shirt with generous portions of the sleeves and neck cut away. Leaning forward at all would give anyone standing to the side or in front of her quite an eyeful.

We put on our most innocent expressions as we watched James trying not to stare when we met him at the front door. It was almost funny to see how big his eyes got! I wish I could have seen his expression when the three of us turned around and gave him a great view of 3 beautiful butts with only a small string going right up the crack!

James was true to his word and himself wore just a t-shirt and underwear. He had on a tank top that went just past his crotch, almost hiding the light gray bikini briefs underneath.

We started off our evening of fun and exhibitionism by offering James some food and drinks we had prepared. We had practiced our moves and pulled them off to perfection. Stephanie made it a point to brush his arm several times with those incredible tits of hers. I made sure he was looking my way when I reached up to get a glass out of the cupboard – lifting my cutoff shirt well above my nipples. Erin was all around him bending over to hand him things or pick things up. One time when she bent over, I almost laughed out loud when I saw him trying to decide if he should look at her tits showing in the gaps of her shirt or her pussy lips that were starting to peek through the skinny thong bikini.

I also saw him trying to hide the growing bulge in his underwear. We had all decided ahead of time that we would not look or let on that we knew we were giving him a raging boner. But it was becoming more difficult as I realized that what we were doing was also turning me on! As I looked at Erin and Stephanie, I realized I was not alone. Stephanie's hard and thick nipples were poking out from her t-shirt so far I thought they would rip right through. I noticed Erin kept slipping her finger down for quick brushes against her clit whenever James had his eyes glued to Stephanie's tits. While I had seen both of them naked many times in the school locker room, I had never seen them like this and was surprised to see how turned on I was getting just watching them!

Once we had eaten and gotten through the small chat, it was time for phase 2 of our plans. I proceeded to let James know about our supposed class assignment.

"Thanks again for coming over James. We really needed a guys help for this assignment in our Psychology class. Right now we are studying the male personality and how sex affects a guys thoughts and actions. We have a survey that we are supposed to ask a guy. So we need to ask you some questions, both to build a profile on you and then get your input on a variety of issues regarding sex."

We knew that in order to pull this off, we had to be very nonchalant and act as if discussing these kinds of things were something we did with guys everyday. So we ignored the incredulous look on his face and just got right to the questions. We had typed up an official looking form and started to read off the questions and write down the answers.

"Let's start with your basic profile" "Age?" "19" "Height?" "6 feet, 1 inch" "Weight?" "182 pounds" "Schooling?" "Freshmen in college" "High school GPA?" "3.78" "Siblings?" "1 younger brother and 1 older sister" "Sexual orientation?" "Um…well, I like girls if that is what you mean" "Number of sexual partners?" "Well, I didn't think this would be … I mean, you have to know this kind of stuff?" "It is required for our project and the profile – it won't mean anything if we don't get accurate info." "This is embarrassing, but I haven't had sex with anyone yet." "Ok, I got that down. Now we are down to the last question for the profile. On average, how often do you masturbate each week and where do you usually do it?" "You have to know that!?" "Well I know it is a bit personal, but we need this for research. Look, if it will help, so you won't feel so singled out, how about if we all share the personal details about how we masturbate? Stephanie, do you want to go first?"

You can imagine that by this time, our nice guy James was a little flustered. Judging by the growing lump in the front of his jockey shorts (which had finally subsided a bit earlier), he was getting thoroughly excited as we got into our own masturbation details.

Stephanie started off by going into explicit details of how she liked to masturbate in the shower, usually every day. She shared with us how she liked to first take the soap and rub it all over her body. Then she would explain how much she liked to caress her tits and nipples. As she described what she does in the shower, her hands started to roam across her own body. James wasn't the only one in the room who got excited when Stephanie pinched and pulled her nipples to show what really got her off. She continued to explain how good it felt to rub her clit with one hand while pinching her nipple with the other. As she talked her other hand started to drop down in between her legs. She was moving a little ahead of our plans, so before she could go any further I interrupted to say it was my turn to share.

I very calmly explained how I usually masturbated each night in bed before going to sleep. I looked James right in the eye and held his gaze as I went into details about the various things I would use to reach an orgasm. I could see him start to tremble a bit as I told him how good it felt to use a vibrator all over my clit and in and out of my cunt. His eyes went wide as I shared how much I liked to take a long string of fake pearls, slide them all the way up one leg until they circled me and then rub them back and forth along my clit, my cunt and even my butt hole. I admitted that I didn't always reach a climax, but even when I didn't, the effort still felt great!

Now it was Erin's turn. She told us how she usually masturbated each morning during her morning stretching. Being a gymnast, she had to stay limber and each morning she would sit in front of her floor length mirror with no clothes on and go through her stretching exercises. Erin mentioned how much it turned her on each morning with her legs spread way out to look at her pussy in the mirror. She would then lay on her back, with her legs spread out in complete splits, her head up and looking in the mirror. My own pussy was aching to be touched as she explained how much she enjoyed seeing her own fingers rub her clit and extend down into her cunt. With an embarrassed grin she even shared how often she had tried to make herself cum with her own tongue – but so far, she couldn't bend quite far enough.

Once Erin finished talking, we all turned to look at James. He knew it was his turn. We also knew that like the rest of us, he was incredibly turned on. He had his hands in his lap – I wasn't sure if it was to hide his erection or give him a chance to touch it. We continued to ignore that part of his anatomy and act as if sharing the details of how we masturbated was something we did everyday. The truth was, we had never even discussed it amongst the three of us. I liked knowing that Stephanie and Erin seemed to masturbate as much as I. And replaying in my mind what they would do to climax was making me quite wet and sending shivers all the way down to my toes.

With a quiet voice, he began to share some details on what he did to masturbate. What was funny was that he did a little of what each of us did! He usually jacked off each night before going to bed by using some lotion or by laying on his stomach and rubbing his dick up and down along the bed. He would often get off in the morning when he took a shower. He seemed a little less shy as he explained how he would first point the shower head at his dick and try to hold still so he could get a strong stream hitting just the underside of the head. Next, he would usually put conditioner in his hand and jack off till he came. He also shared how much he liked looking at himself in the floor length mirror in his room when he was naked. He would look at himself from different angles and watch his dick as it slowly got harder and longer. Sometimes he would do jumping jacks and watch his dick jump up and down. Other times he might do various sit-ups or stretches while keeping his eyes glued to his boner. He would sometimes press his dick against the mirror or slap it softly from the underside. But the best, he said, was to stand in the mirror watching himself as he jacked off and the sperm went flying when he came.

In as professional a manner as I could, I thanked James for sharing those details. I had actually forgotten to keep taking notes as I got so involved listening to him describe how he jacked off, but I don't think he noticed. Now that we had gotten ourselves loose and more open to discussing the intimate details of our sex life, us girls knew we were ready for the third phase of our plan.

"We are done with the profile part of the survey and now are supposed to get more detail from you on your preferences. But some of these questions have to do with what you like to do during foreplay and sex, but since you are a virgin, you can't answer that! Now what are we supposed to do? Maybe we have to find some other guy."

I felt so bad and almost called the whole thing off when I saw the stricken look on his face when I said we would get somebody else, but I knew we still had lots of good stuff planned for him, so I continued on with our plan.

"Well, since you are here we can at least run through the questions and see what we can do. Ok, the first question is what size of woman's breast you most like to fondle – small, medium or large?"

He looked pretty dejected when he explained that he had only felt one set of breasts before when making out with a girl last year – so he didn't have any basis for comparison. This was just what we were hoping for! As if I had just thought of it I said, "Well, since between the three of us girls we have all 3 breast sizes, I guess we could let you touch us. It's either that, or we won't be able to complete this assignment tonight. Erin, Stephanie, what do you think?"

As they pretended to think about it and reluctantly agree, I noticed a little jump in the bulge in James underwear at the thought of touching our breasts.

So the three of us stood up in a line and waited for James to grope our breasts. We left our shirts on and just waited for him to start feeling us out. He very hesitantly reached down to squeeze Erin's tits first. He gently cupped first one then the other and then rubbed his fingers along her nipples. Her tits weren't large enough to get a whole handful, but I could tell they both enjoyed it as he squeezed them through her shirt.

After a minute or so he turned to me. My nipples were already hard just thinking what his hands would do. He was a little bolder this time as he filled his hand with my left breast and proceeded to massage it lightly. He avoided the nipple at first, but then caught it between two fingers and gave a little pinch. It was all I could do not to cry out with pleasure! He then moved behind me and cupped both my breasts in each hand. I loved the feel of his hard dick brushing my butt as he gripped my tits from behind, but I pretended not to notice. He was now squeezing both my breasts firmly while lightly pinching my nipples with his fingers. Unfortunately, my turn was over too soon.

He went to Stephanie next, but started from behind her and put both hands under her tits and lifted them up a bit. He tried to cover the entire breast with one hand, but they were just too big. He moved around to the front and put both hands on her left breast and began to massage more aggressively. He must have remembered what Stephanie had said she liked in the shower, because he supported the breast with one hand while pinching her nipples with the other and pulled it out quite some way. I was amazed how far they came out! Stephanie gave a little grunt and James quickly let go and apologized for hurting her. She quickly assured him that it had not hurt, but that she had enjoyed it. She gave him that amazing smile of hers and I think he almost came right then!

We all sat back down and I tried to hide the lust I was feeling as I asked James which breast size he had liked the best. He said he felt like Goldilocks and the three bears as he explained that Erin's seemed a bit too small, Stephanie's were a bit too large, but mine were just right.

I wrote his answer down and covered my surprise that he had chosen my tits over Stephanie's. Based on the looks Stephanie's tits got from guys all the time, I assumed James would pick hers. I was enjoying this more than I thought I would! Now that we had let him touch us, our plan called for us to next see if we could get him totally naked. This was great! Everything was going just as we wanted! That would soon change.

"One of the big discussion items on this topic is guys and penis size. It seems that a big part of the male ego is tied into how comfortable he feels with the size of his dick when erect. So we need to know from you how big yours is, if you like your size and if not, how big you would like it to be?"

James looked down embarrassed and didn't respond at first. Then he started to get up and kind of mumbled that he should probably go home now! I was shocked! This wasn't supposed to happen! I gently put my hand on his chest and asked him what was wrong? At first he wouldn't respond, but at last he spilled his guts.

It seems James was pretty sheltered and had only seen one time what other guys looked like with an erection – a porno movie seen at a friends house when he was 15. Apparently it was a movie on guys with massive dicks and he could not believe his was so much smaller than theirs. Even though he had read up on what was the normal size, he was never sure where exactly to measure from and was sure that he must be small compared to everyone else. Suddenly I realized why this nice guy was still a virgin. Not only was he shy and too nice to try and push himself on a girl, but he was also afraid what a girl would think of the size of his dick!

"James," I said, "I am pretty sure you don't have a thing to worry about when it comes to the size of your hard-on. I have seen it trying to get out of your underwear and it doesn't look that small to me. But to put your mind at ease, why don't you let us take a look and we will let you know how you compare to others we have seen. If you want, I could even measure it for you."

"You want me to just stand in front of the 3 of you naked while I let you stare at my dick?"

I could see he was pretty self conscious, so without saying a word I just lifted off my shirt and pulled down my underwear. I was only a foot away from him and totally naked. I gave Stephanie and Erin each a look. They both understood and proceeded to remove their tops and panties as well. Both James and I were looking at Stephanie as she peeled off that tight tank top – that was a sight to see!