Man Boobs

By bustedbyruddysat15

Has there ever been someone you knew in real life who was so close to a sexual fantasy that you couldn't believe they were actually flesh-and-blood? Well, I was lucky enough to know TWO such people: Identical twins Eva and Ava Bennett.

I've been holding off writing about them for a long time, because the memories are so painful, and writing about them is much less fun than writing "Hall of Fame" entries or posting pictures of beautiful women in bikinis. But this website is about documenting my humiliations, so I suppose I have to do it sometime.

When I was in 10th grade, I transferred to an exclusive residential academy some 200 miles away from home. While it was often stereotyped as a "nerd school," I discovered that the distribution was just like any other school: "cool" kids who were obnoxious assholes, "nerds" who were painfully socially inept losers, and a large middle. When I first came to the school, I was part of that middle, but as my personality began to show through I was quickly classified among the losers.

The fact that it was not immediately obvious that I was a nerdy loser is the only reason that Ava Bennett ever talked to me. She and her sister were identical twins, but she was the prettier and more flirtatious of the two. Both sisters had gorgeous faces, lovely dark blonde hair, and long, lithe, flexible bodies. And their legs ... oh Lord. Legs like that are all it takes to remind me why God made women.

Some of my peers believed that another girl in our class, Emily Sanderson, was the hottest, because she had pretty big boobs for a high schooler. But I've never been into boobs, so I barely gave Emily a look. No, legs have always been my fascination, and that's why Ava was always the number one hottest girl in the school for me, with Eva close behind at number 3. (Number 2 was their close friend Edie Flagg.) Ava, Eva, and Edie were all cheerleaders, and when they came to school in their cheerleading outfits, the boys' bathrooms were always full. I have a distinct memory - and I swear, this is a 100% true story - of Ava coming up to me on a day when she was dressed up (tight blouse, short skirt) and asking me for help on a math problem set. I gave her the help she needed and then excused myself, ran at top speed back to my room, and gave myself a thorough spanking. That is the only time in my life I've ever lost my sense of self-control so readily.

Anyway, after that introduction if I told you that Ava and I were friends, you'd think I was lying, but I swear to you it isn't so. We met very soon after coming to the academy, and I hadn't yet gained a reputation for loser-dom. She and her sister had come from an all-girls Catholic school, and she was very outgoing and flirtatious, with a bit of a thing for nerds. She asked me on a date (NO, REALLY, SHE DID - I SWEAR!!!) and I accepted. During the date, my lack of social skills became obvious, and she sweetly but firmly dropped me down to "friend" status. (I responded by sweetly but firmly wrapping my hand around my cock a minimum of five times a day for the next six months.)

I remained in the "friend" position for both sisters for the rest of my sophomore year. But the next year, things changed. Social circles began to reify, and the girls consolidated their positions as queen bees by dumping their nerdy buds, of which I was one.

None of the guys liked getting dismissed by their hot female friends, but as nerds they lacked the social capital to do anything about it, so they quietly retired to the privacy of their bedrooms and fantasized about what might have been. (I heard that one of the more arrogant geeks, a dude named Kenny, tried to get in Ava's face, and she responded by kicking him in the groin, but that may just have been an urban legend.)

My first hint that the girls had a dark side actually came during the first year that I knew them. Ava and I worked in the same office. One afternoon, our supervisor went home early. She left us a key and told us to clean up a back storeroom. Anyway, we got to work. Ava was dressed pretty nicely - blouse and skirt again - so I ended up doing most (read: all) of the heavy work, while she did a little bit of filing and looked after her nails. Around 4:30, her sister and Edie arrived. She technically wasn't supposed to leave until 5, but she asked me to sign her out at that time. I regretfully told her I couldn't do it. She nodded and said she understood. Then she winked at Eva and Edie. I wasn't sure what that meant, and for a second I was suspicious, but then she said, "Well, I guess I'll just have to help you get done as quickly as possible." Wow, I thought to myself, what a sweetheart.

Then she bent over to pick up a heavy box marked "FRAGILE." Now Ava was quite the athlete, a skilled gymnast and member of the cross-country and soccer teams as well as the cheerleading squad. However, the fact is that even a weak guy has more upper-body strength than a strong girl, so when I saw she was struggling I quickly told her not to bother and picked it up myself. To my surprise, it was far heavier than I expected. Also, I had been doing heavy lifting for the past hour or so, so my arms were pretty weak.

Anyway, I almost dropped it, and Ava called out, "Careful! You don't want to break it." I had no idea what "it" was, but I knew that I would get in trouble if I wasn't careful, so I balanced the weight in my arms. Realizing that I wasn't strong enough, I shifted it to over my head. That made it easier to hold up, so I looked around for a place on the upper shelf to put it down. Too late, I realized that there was no room!

I looked at the girls, who seemed to be silently giggling. It's not that funny, I thought to myself. Just then, Eva stepped forward. "Hey Man Boobs," she said, "You wanna see the new cheerleading move we've been practicing?"

With my hands above my head, my balance was fine, but I couldn't shift without the danger of dropping the box and breaking its contents. In other words, my hands were stuck in the "up" position. I couldn't protect myself. Of course, at the time I didn't think I needed to - it was only in retrospect that I realized how skillfully Ava had maneuvered me to get me right where they wanted me.

Anyway, at the time I had absolutely no idea what to do. Three super-hot hotties - the three hottest girls in my class - were standing in front of me, wearing short skirts and offering to practice a cheerleading move on me ... uh, I mean, in front of me (sorry, foreshadowing). Well, what should I have said? What would you have done in my situation?

"Uh ... okay," I replied, trying to sound "cool" and noncommittal without actually declining. Eva smiled disarmingly. "Thanks so much!" she said. "Here ..." She organized the other girls next to her, Edie on her left and Ava on her right, directly in front of me. I could feel my dick stiffen. "Ready? Okay!"

The girls whirled around, their skirts swirling in a way that brought out my full 4 inches. Then Edie, smiling brightly, did a swift and powerful front kick. Eva followed suit, also smiling. Despite my naïveté, it was now starting to dawn on me what they had in mind. Ava smiled wider that I thought humanly possible. As horrified as I was, I was also 100% aroused. She brought her knee up and made eye contact with me. Her expression did not change, but I was sure I saw a twinkle in her eye.

Then, in a flash, came the kick. Completely immobilized, I closed my eyes and flinched in preparation for the blow - a blow which did not come.

When I opened my eyes, I saw that she was holding her foot just an inch away from my boy parts. All three girls burst out laughing. Slowly, she raised her foot into my crotch. I could feel my balls being lifted up and lightly pressed against my pelvis. She did this a couple more times. The message was unmistakable: I own you. I can manipulate you. I can destroy your manhood any time I feel like it.

She lowered her leg to the ground. "Bye, Man Boobs!" she said with a smile. "Sign me out at 5, ok?" I nodded, powerless to object. Then she and her friends took off. I was in no pain, but I got no work done the rest of the evening - I was too busy jerking off.

PART 2

So yeah, enough about the good old days of 10th grade, when Ava and I were still friends. Like the rest of her nerd ex-pals, I was crushed when she stopped saying "hi" to me in the hallway and brushed me off when I tried to talk to her. However, my reaction was straight-up posing. I didn't tell anyone about her change in attitude; instead, I carried on like we were still tight, and I started making broad innuendos suggesting that we were more than friends. (I had been seen in public with her just enough times to make this - barely - possible.) Anyway, there was a common perception among the male population of my school that the twins were sluts (in reality, both were strictly observant Catholics), and I subtly encouraged this perception.

I was a lot more brash in those days, so I didn't really care about what happened if my macho bragging happened to spread beyond my circle of nerd-loser friends. That's why I made a fateful mistake one day in my biology class. The teacher was discussing identical and fraternal twins. He brought up the Bennett sisters and said that he couldn't tell them apart. He then asked if there was anyone who could tell them apart. I said that I could, which was true - I had spent enough time with them to notice subtle difference, and in any event Ava was definitely prettier. But when he asked how I told them apart, I decided to be cheeky. I was about to say, "By smell." But then, at the last second, I changed it to what I thought would be a funnier punchline: "By taste." But instead of a laugh, all I heard from the class was "Ewwww." Too late, I realized the sexual implication of what I had said.

Compounding my fate, I decided to play it up and act like I was a player by laughing naughtily. Big mistake.

Naïf that I was, I honestly didn't expect the news of my faux pas to extend beyond the walls of my biology classroom. My first indication that it had was a run-in with my nemesis, Clarence Longdick. Clarence was an annoying but genetically blessed jerk who somehow managed to get dates with every girl that I had a crush on, then turn them against me. (He ended up following me to my undergrad school, where he got a hot kinky Asian girlfriend the first semester and proceeded to have sex with her regularly for the next four years. And yes, he's still an asshole.) Anyway, later that day I passed Clarence in the hallway. He wasn't in my bio class, but I guess he had friends who were.

"Hey, I heard you said you gave head to the Bennett twins," he said to me smarmily.

I was a bit surprised that my thoughtless comment had spread so far in such a short time, but I foolishly figured it couldn't do more than enhance my "rep," so I just laughed and said, "Maybe."

I expected him to make some smarmy reply, but instead he looked genuinely concerned. "If I were you I'd stay away from them," he said. "I heard they were pretty pissed off."

"Good one, Clarence," I thought to myself. "I'm sure you want me to stay away from them - so can spend more time around them, slandering me!"

Of course, in the back of mind, it occurred to me that if Clarence had heard about it, the Bennetts probably had as well, and they probably were pissed off. But so what? It's not like we were friends anymore, and besides, what could they do to me? I no longer saw them on a regular basis, and anyway they must know that I wasn't serious, right?

I didn't give it much thought until later in the day, when I was preparing to go back to my dorm. All of a sudden, Edie approached me, smiling. This took me by surprise, because Edie and I had never really spoken. We weren't on bad terms, but we weren't on good terms either - we were just kind of indifferent. (In fact, as hot as she was, I only masturbated about her when my fantasy also included Ava and Eva.) Anyway, she pleasantly asked me to come to the weight room to help her lift something. I was instantly suspicious. First of all, as I said, Edie and I don't know each other, so why would she approach me out of the blue to ask my help? Secondly, why would she ask me, bypassing all those guys who had, you know, muscles?

I happen to be of far-above-average intelligence, but even if I were just average I could have guessed what was coming. But how exactly does a male say no to a sexy girl asking for his macho help? I had no choice. I followed her down to the deserted weight room. When I got there, Ava and Eva were waiting for me. Just as I registered their presence, Edie grabbed my right arm. Eva walked over and grabbed my left. They let me struggle for several seconds, until I gave in. Of all the differences between men and women, the only one in which men are truly superior is that they have, on average, greater upper-body strength. Well, my upper-body strength had been tested against the strength of these two very-feminine babes, and I had been the loser. (On the plus side, that little struggle remains the most intimate contact I have ever had with a female.)

Ava stood in front me, fixing me with her gaze. I was by now resigned to whatever would happen to me, but the sight of her still made a chill go down my spine (and gave me a full erection too, I might add!). She looked me straight in the eye. "Sorry, Man Boobs," she said, "but you brought this on yourself."

I nodded, realizing that she was right. "Thank you for not doing this in public," was my only reply.

She drew her leg back. Eva and Edie each held one of my arms to keep me from covering, and they each hooked a foot around one my legs to keep the target from closing. I braced for the impact. Ava leaned back into kicking stance.

BAM!!! I had been preparing for Ava's kick, but Ava hadn't moved, so I was caught completely off guard. No, it was Eva who had swiftly pivoted from her position on my left and racked me with her knee. Her cheerleading training had given her speed, power, and accuracy, and I was the recipient of all three. I was still reeling from the blow when Ava finally released her full-force front kick.

From that point onward, I pretty much lost the will to live. Ava unleashed four more blistering groin kicks before Eva had a chance to get in a second knee. They alternated like that for several minutes. Every so often, I would feel a hard punch to my 'nads from behind, and I knew that Edie was getting in on the action too.

15 minutes later, I had paid for my mistake many times over. My balls were swollen to three or four times their normal size (which, I must confess, was rather tiny). They were red, and I knew that I would be pissing blood for the next couple of weeks. I could not stand under my own power, which means that when Edie and Eva let go of me, I slumped to the ground and lay there like a sack of potatoes. I knew that it would be prudent to at least cover my crotch with my hands, but I lacked the strength. Instead I just lay on my back, looking up into three of the most beautiful faces I had ever seen.

That's when Eva said exactly the four words I was hoping not to hear: "It's not over yet."

I lost it. Whatever scrap of manhood had been holding back my tears was now gone. I sobbed like a baby.

After a couple minutes, Ava extended her arm and helped me up. "Don't worry," she said soothingly. "We're almost done. You see ... we decided to do this in private to avoid humiliating you. But we still need some proof, so it doesn't look like we let it slide."

The girls quickly and efficiently stripped me to my underwear. (Thankfully, they were too polite to say anything about my man boobs.) Edie got out a digital camera. The Bennett sisters flanked me. They did that common pose girls do where they lift up one knee - except that that knee was placed directly in my groin. As the shutter snapped, I felt the impact lift me off the ground a few inches as my jelly-bellies were mashed into my pelvis. The resulting picture - a perfect vision of emasculation - got passed around our school and even circulated on the Internet for a while. You've probably seen it, and laughed at the poor pathetic schmuck in it. Well, my friends, I am that schmuck.

PART 3

If you think that after that incident I would never speak to the Bennetts again, you've underestimated the extent to which I am a slave to the skirt. Within a few days of my near-castration, Eva and Ava were smiling and saying hi when they passed me in the hall, and even though I never dared approach them or speak to them, I felt that we had a certain level of intimacy.

Things continued like this into the following year, my senior year of high school. By this time it was 100% obvious that I was going to graduate from high school a virgin, and I had surrounded myself with similarly unlucky friends. One of my best friends was Mark Baker, a tall, reed-thin nerd with thick glasses who, even more than me, was a total horndog. Anyway, Mark, my other friends, and I would often get together and talk about which women we had talked to, which ones had smiled at us, which ones' skirts we had gotten a peek under - in other words, locker room talk, except that none of us had ever touched a woman.

It was during one of these conversations that Mark told me that Ava and Edie were sitting at his table for math class. For a long time, I had been the envy of my group of buds because I had once been friends with the Bennetts, and they still said hi to me when they passed me in the hallway. I enjoyed letting my friends think I had some kind of mojo that gave me an "in" with these goddesses - none of them, of course, knew about the weight room incident - but in fact it had been a long time since I had a conversation with either of them. Now, here was Mark, telling me that he had sat down at a table in math class and, a few minutes later, a goddess and her gorgeous best friend had joined him! I couldn't believe it. Now, if it had been my friend Ben Freeland I could have understood - Ben was widely regarded as a math genius, as I mention in this post. But Mark?! Mark was a rather poor math student. I simply could not believe that those girls were depending on him for help. But the alternative - that they found him attractive - was even more unlikely. Right? I was sure it couldn't be so, but the possibility gnawed at me. I was consumed with jealousy.

I mention all this as background for an incident that happened one day during the first semester of my senior year. I was approached out of the blue by Eva Bennett. Naturally I was pleased to see her, though my privates did ache a bit at the memories she stirred up. Anyway, she asked to speak to me alone, and I complied. Then she informed that she wanted my help in playing a trick on Mark.

"Her too??" I thought despairingly. Up until a few weeks ago, I had been the only member of my clique of friends whose existence Ava and Eva were even aware of. Now both sisters were on first-name terms with Mark, and so intimate that they were playing pranks on him? I bit my lip, hoped that my skin wasn't turning green with envy, and heard her out.

This was her plan: She told me to start a conversation with Mark. While I kept him engrossed in the conversation, she would creep up behind him and play a game of kickball (my phrasing, not hers).

I was flabbergasted. This was Eva Bennett, the sweet, friendly, Catholic-school girl I had once known? Yes, she had kneed me quite hard in the balls several times the year before, but I had deserved it for my piggishness. But a groin kick done as a practical joke??!! On my best friend?! There was only one possible answer I could give: Yes.

"Yes"? That's right. You see, the green-eyed monster had consumed me. I just couldn't wait to see my best friend doubled over in pain while a cheerleader and I high-fived and laughed at him.

Eva and I quickly made the arrangements for time and place. I lured Mark to the appointed spot and started engaging him in conversation. I don't remember the subject, but he seemed very enthusiastic about it too, and our discussion was unusually animated.

In the middle of it, I noticed Eva, wearing a short skirt, sneak around behind Mark. She gave me a big smile (which I returned, though Mark didn't notice) and a thumbs-up. As I continued to distract Mark with my sparklingly witty comments, she positioned herself behind him. Mark still didn't suspect a thing as she tensed herself and then unleashed a dynamic kick at his fun-bag. In my mind's eye I could see exactly what would happen next - the look of disbelief, the doubling over, the sheer joy in Eva's face - and I could feel my heart pounding in anticipation. Eva's shapely leg traced a perfect arc that ended in full-force contact with Mark's scrotum - and at that moment, I felt a searing pain in my genitalia!

I must have blacked out for a split second, because the next thing I knew both Mark and I were rolling on the ground, holding our privates and writhing in agony. Eva was laughing her pretty little head off, and as she did so, AVA walked over to her from behind me, also laughing, and they exchanged high-fives! WHAT THE FUCK????!!!!!

Slowly, as my brain was able to function again, I pieced together what had happened. As Eva had snuck behind Mark and kicked him, Ava must have done the same thing to me. But wait ... if she were behind me, surely Mark must have seen her, right? So then why didn't he say or do anything?

That's when the full truth sunk in. I now recalled some odd smiles and gestures Mark seemed to be giving when he talked to me - actions that seemed to be directed to someone vaguely behind me - but I didn't turn and look because I was too busy staring at Eva! Here's what must have happened: Ava had, at some point prior to my conversation with Mark, approached him with the exact same offer that Eva had made to me - except with me as the victim!!!

Let me be very clear about one thing: Mark and I were, and still are, extremely close friends. We have gone through many things together and almost always been there for each other. But we were both willing to help in getting the other humiliated and emasculated while we just stood and watched. We had both been willing to stab the other in the back for the sake of a pretty cheerleader who didn't even care about us.

As we lay on the ground, Ava took pity on us. "Don't take it personally," she said. "We just wanted to see if we could get two good buddies to turn on each other, and we chose you guys because ... well, you know." She left the termination of her phrase uncompleted: "... because you're both nerdy losers, because neither of you has anything of value between your legs, because you're both so insecure that you wouldn't dare make a complaint, because it doesn't matter if we do permanent damage to your sexual organs because both of you are going to die as virgins ..." and so on.

Eva smiled as well. "I guess it's 'chicks before dicks' for you guys!" she said, laughing.

Mark and I are still best friends - we saw each other over the past school break, and spent New Year's Eve together, in fact. But we never, ever spoke about our run-in with the Bennett twins - and we never will. While I can't speak for Mark, I think I know the reason why. You see, as I lay on the ground cupping my privates, watching two super-hot chicks in short skirts laugh and congratulate themselves on causing my pain, I couldn't help but well ... rub myself. Down there, you know. And I had what I must confess was the best orgasm of my life. I suspect that Mark did something similar. And well ... you know how classical conditioning works. Over the past several years, I have done an extremely good job of convincing myself that I'm not gay. But when my most satisfying sexual experience came in the presence of my male buddy - when I still can't look at that buddy without feeling a tingle "down there" - well, even I begin to have to have my doubts.