tagExhibitionist & VoyeurDweeb, Dwoob & Mike - A Love Story

Dweeb, Dwoob & Mike - A Love Story


I'm rather insecure. It's my looks. I don't have an hourglass figure, for example. My hips look like they belong on a man. It's called "slim hips" and women runners have them. I just call them ugly hips. My face is not especially pretty and my hair is in a permanent Jewfro, the type of tight curly hair Jews get that resembles genuine afros. On Blacks it can look attractive. On me, not so much. I'm not even Jewish, either. My name is Mary for Pete's sake. No Jew is ever named Mary.

I'm too skinny and my legs are not shapely. They resemble toothpicks, one could say. I've tried to bulk up a bit but I have the metabolism of a thoroughbred racehorse and I simply cannot put on any weight except in one place. All my body fat is in my boobs, I'm sure.

I have two good features. The first is I am lucky and have good skin. I am the iconic woman who is soft and smooth. I have the kind of female skin that men just love to stroke. My second feature is more impressive and apparently if you're a man it's a doozy. As you have guessed by now I have great boobs. That's it. My sex appeal lives and dies with my boobs. Mostly, it seems to me, it dies.

The good news is that at long last I have boyfriend. The bad news is he's a dweeb. He shares an apartment with another dweeb. I thought about calling him dweeb one and his flatmate dweeb two in a nod to The Cat in the Hat by Dr. Seuss. Instead I think of them as Dweeb (my boyfriend) and Dwoob (my boyfriend's flatmate).

I don't love Dweeb. I'm not sure I even like him. Our relationship is symbiotic. I get the status of having a boyfriend which was something I really wanted. He gets all the sex he can handle. I try to keep him happy on that score. I do all the tricks I can think of, such as moaning when we do it, calling him 'Big Boy,' giving him wonderful blowjobs, masturbating for him while he watches, letting him fuck me in the shower, and trying every position we can think of. I even gave him a copy of the Kama Sutra for his birthday. It works. He is either in love with me or too enraptured with our sex ever to give me any trouble. I'm his first and so far the only girl he's ever laid.

I've even left my comfort zone for Dweeb. He's never said it but he wants me to tease Dwoob. He wants me to drive Dwoob crazy. At his request in the mornings I wear a T shirt and panties, with no bra. My nipples poke prominently at the T shirt and my boobs have what Dweeb calls 'independent suspension' as they jiggle around when I parade around the apartment.

My panties too are sheer panties, so when I bend over Dwoob gets some pretty nice looks, I'd imagine. At one point Dweeb upped the ante by having me wear one of his T shirts which was much too big on my skinny frame. It was a V neck and it showed off an enormous amount of my braless boobs. The exposed boobs went right up to the nipple, but luckily did not include the nipples. I have long nipples and they always poke prominently when I go without a bra.

I was careful not to bend over. I knew (later verified when I bent over in front of a mirror) that my entire boobs, nipples included, would be exposed to Dwoob if I bent over. I got through the T shirt tease okay, but poor Dwoob was a mess. He had constant morning wood just from looking at all of my exposed luscious boobs.

My biggest fight with Dweeb happened when I asked him to go with me to a sample sale out in Brooklyn. It was for clothes by the designer Maria Cornejo. Her stuff is expensive. I developed the habit of going to her retail store in Manhattan from time to time just to drool and fantasize about her clothes. I never bought anything because I'm not yet rich enough.

With a sample sale though, I could compete. Sample sales offer clothes at deep discounts. Even severely marked down her clothes were pricey for me. I asked Dweeb to come with me to tell me if I looked good in various outfits, or not. I have trouble making decisions when the clothing is expensive. I figured if Dweeb said I looked good, or (better) even sexy, then I would have the courage to spend the money and to get something.

Dweeb refused to go. Worse, he said, "Oh grow up. You don't need me to choose clothes. I'm not that kind of a wimp." After a huge fight and the throwing of some pottery coffee cups, I stormed out planning to return to my rarely used postage stamp sized studio apartment in deep Brooklyn.

At one point, I noticed Dwoob was following me. He was keeping a distance, trying to be discrete, but he was definitely following me. I went to the F train, which is the one that goes to the sample sale which was in Carroll Gardens, a pleasant neighborhood of Brooklyn. Sometimes one has to wait on the platform a long time for the F train to come, and after the second M train had come and gone, I walked over to Dwoob (whose actual name was Mark). "Are you following me, Mark?" I asked him, point blank. "Or did you just have a sudden urge to take the F train?"

Perhaps I stood too close to Dwoob. My braless boobs were almost touching his chest. For whatever reason, Dwoob was flustered and had trouble speaking. I had an epiphany. "Mark," I said, "Do you want to help me out at the sample sale, seeing as how we're both heading that way?"

Dwoob nodded and forced a smile. I said, "Mark, you're a doll." I gave him a kiss on the cheek. He blushed. I had epiphany number two. Mark had never been with a woman before. The man was a virgin. I don't know how I knew that. I just knew it.

Was that really surprising? After all, I am Dweeb's (or using his given name, Joshua's) first and only sex partner. Dwoob was just one girl friend slower than Dweeb. I had an evil thought. Could I even be that evil I asked myself as a plan formed in my cute little deviant mind.

Dwoob of course had no idea what it's like at a sample sale in New York. Why would he have known? The place was packed with women, and almost no men were there. There were a few mirrors scattered about but there were no changing rooms. If a woman wanted to try something on she would simply strip down to her bra and panties and slip on an outfit.

Dwoob's eyes bugged out as women, some with dynamite bodies, were all around him. They were riffling through the racks of clothes and a significant portion of them were dressed only in bras and panties, looking for another outfit to try on. All women know how these things work and they wear non-revealing bras and panties, although some wore see through lace bras. Then there were women like me.

Dwoob did not know where to look. I'm not sure if he had ever before seen a woman dressed only in a bra and panties and his eyes were frantically going everywhere at once. I browsed the clothes waiting for him to get acclimated to the women in underwear all around him. I began to despair that he might never get acclimated. I discretely noticed he was trying to hide an erection. His erection seemed to me to be a nice reward for his having agreed to come there with me.

Finally, he appeared to be a little calm, or at least a little less nervous. He had developed a technique of studying his shoes to avoid staring at all the barely hidden boobs encased within see-through lace bras. When he looked up he quickly became mesmerized again and his erection returned. The poor guy. Then he would study his shoes some more.

I came up to him during one of his periods of the close study of his shoes. By the way, his shoes were scuffed and dirty and in my opinion required a serious shoe shine much more than a close study. Standing in front of him, I asked him to hold the five items I had chosen to try on. He did. I removed my dress. I was, I think, the only woman there who had not worn a bra to the sample sale.

Dwoob's face became bright red. I smiled at him as he stared at my boobs, finally seeing them for the first time. I asked him to hand me one of the dresses I wanted to try on. I glanced down and saw his erection had doubled in size. Suddenly I realized that Dwoob was really hung. I filed away that little factoid. Well, I guess it was a big factoid, wasn't it?

I tried on the first dress. I went through all the little modeling moves we women always do, and said, "Now remember how I look in this dress, please, Mark." Dwoob nodded. I took off the dress revealing again my naked boobs to the poor man. I wanted just to fall to my knees and take his schlong into my mouth to give him some relief. Sadly though one simply cannot do such things in public in the middle of a sample sale.

I did think about it, though. It would be an amazingly stupid thing to do with Joshua's flatmate, no matter how mad I was at Joshua just then. I tried on five outfits, each and every time showing off my boobs to Dwoob. To my surprise Dwoob gave me great advice and I ended up spending more money than I could afford but getting some great deals and some gorgeous new clothes. The sample sale accepted credit cards, thank goodness.

Afterwards we went to the nearby bakery Bien Cuit and had some rolls and a damn good espresso. I said to Dwoob, "Thanks a lot Mark for having come with me. I got some really nice clothes."

Dwoob blurted out, "Mary, you have the most beautiful boobs in the world. You looked super-hot in those clothes."

I smiled at Dwoob. After Bien Cuit I told Dwoob I was going back to my tiny studio apartment in deep Brooklyn. He looked crestfallen. I said, "Do you want to come with me? There's not much to see in my tiny apartment, but there's a nice park not too far away?"

Dwoob cheered up. "I'm glad you're coming," I said, giggling over my double entendre. I wondered if he had prematurely cum in his pants already. When we got to my apartment I decided to give him another thrill and I tried on all the outfits again, each time of necessity baring my boobs to him, and my entire body, clothed only in skimpy panties. Dwoob was going nuts.

Dwoob sat in my only arm chair while watching me try on the outfits. There was only room for the one chair. The rest of my apartment was consumed by my queen sized double bed. Most people with apartments as small as mine would have bought a sofa bed, but I hate sofa beds. I'm sure they were invented by the Marquis de Sade himself. If I sleep on a sofa bed I invariably wake the next day with a backache.

"Mark," I said, when I was about to slip on the last outfit, "You like seeing my boobs, don't you?" Not waiting for an answer I said, "Would you like to touch them, too?"

I thought Dwoob was going to faint. He could not even speak to reply. "Or perhaps you'd like to see more?" As I said that, I slipped off my panties revealing my bush to only the third man of my life. I was naked for Dwoob. I sat down on the bed and spread my legs. "Take a good look, Mark."

Dwoob came over to me and hesitantly reached out to touch my boob. Unlike my boyfriend Dweeb, Dwoob was a natural when it came to caressing my boobs. I did not even have to fake the moans. I often had to fake them with Dweeb. He was being so good with my boobs, I did not complain when his hands went south and very hesitantly circled my pussy.

Not only did I not complain, I moaned some more to encourage him. Dwoob seemed to know what to do, too, and he began to finger me sweetly and slowly. Dwoob was only the second man ever to finger me, Dweeb being the first, and it was like night and day. Dwoob got me aroused in under a minute. After five minutes I was as wet as the East River and happily moaning up a storm.

"Do you want a blowjob?" I asked Dwoob. "You've been hard for hours now. You must need some relief?" I did not want to have Dwoob's blue balls on my conscience.

Dwoob finally spoke. "I'd love one," he said.

Dwoob filled my mouth with cum literally only seconds after I began the blowjob. I'm sure it was his first blowjob ever. He surprised me that it was so fast and consequently it spilled everywhere. "Don't worry," I said. "I'll deal with it later. This is why God gave us washing machines."

Dwoob shocked me when he gently pushed me down onto my back, spread my legs and began to lick at my pussy. He clearly had no idea what he was doing. He had probably seen men do it to women on Internet porn or something. It felt nice. I quickly realized if I moaned when he stumbled onto a good spot he would stay there or return to it. I could guide him with my moans.

After around ten or more minutes of this I decided it was time for Dwoob to meet my clitoris. I dislike formal introductions so I simply took his hand and placed a finger on my clit. "Lick there, Mark. Be gentle, it's really sensitive."

Five minutes later I exploded in the most wonderful orgasm of my young life. Wow. Emboldened, Dwoob mounted me and entered me with his long schlong before I could even begin to stop him. He was completely inside me before I reacted quickly enough to protest. I definitely did not want to fuck Dwoob! I had just been trying to be nice, to show how grateful I was. That's why I gave him the blowjob. I had basically considered it a combination of a thank you blowjob and yes, truth be told, a pity blowjob. Dwoob misinterpreted! He misinterpreted big time!

On the other hand, Dwoob's cock inside me certainly felt magnificent. Well, he's already fucking me, I thought. Too late now. Might as well enjoy it! I did, too. I enjoyed every second of Dwoob's fuck. I committed it to memory. It had been my best ever fuck up to that point. That said something about Dweeb and me, I guess, and what it said wasn't good.

I knew now it was over between Dweeb and me. I could not go back after having fucked his flatmate and good friend Dwoob. They were both toast. We did however go back and I explained how Dwoob and I had ended up in bed together at my place.

Dweeb and I had the very predictable huge fight. I ended up giving Dweeb a farewell fuck, then Dwoob a farewell fuck, and then another pity fuck for the helplessly jealous, ruined, and horribly hurt Dweeb. Then I had another fuck with the highly envious Dwoob. Finally I had a fare-thee-well fuck with Dweeb and I got the hell out of there! I had never had group sex before, or maybe you'd call it a threesome? Truth be told I kind of liked it, but I have never admitted that to anyone.

I returned to Brooklyn stinking of sex with five loads of cum inside me and I took a long bath. I went out to a local pizzeria for dinner wearing one of my new outfits with no bra underneath. A man came up to me. He introduced himself. His name was Mike and he was ruggedly handsome. I was not in his league. Girls like me do not date men like him.

Mike explained that he had earlier been to the Maria Cornejo sample sale with his sister, to be nice to her, and he had noticed me. "Forgive me for being rude, miss, but you have the most gorgeous boobs I've ever seen."

"Thank you," I said, blushing. "I'm glad you like them." Well, what would you have said in my place?

"Who was that dweeb you were with? Please tell me he's not your boyfriend and that you are available," Mike said. I loved that he called him a dweeb! I liked this guy already.

"He's not my boyfriend, and he's not a Dweeb. He's a Dwoob," I said in complete deadpan.

Mike ignored what must have seemed nonsensical to him. "Are you free? Do you want to see the new Marvel movie over at the Regal Theater?" Mike asked.

"Right now?" I asked.

"Yes, right now," Mike said. We went to the movies together.

Two dates later Mike got to see my boobs again, and two a half dates later he got to see the rest of me, and two and three-quarter dates later he did what men like to do with naked women in their apartments. He was a keeper, and I used my entire playbook developed with Dweeb in order to keep him happy. It worked. As an extra benefit it also kept me good and happy.

Mike wanted to show me off and later in the summer we went to a beach where some women went topless. I was of course one of the women, exposing my breasts for the first time to an entire beach full of lecherous men. I also wore the skimpiest bikini bottom I had ever seen. I'm sure there are skimpier ones, but believe me, this one was as skimpy as I for one would ever have dared to wear.

Mike obviously enjoyed seeing all the other men lust for my body. I also enjoyed, but tried not to be obvious about it, seeing all the other men plus Mike lust for my body. That day led to two things: unbelievable sex that night with Mike, and bright red, sunburned boobs.

Things gradually escalated from there. First of all, let me say that we really hit it off. We had similar interests and similar beliefs. Mike read philosophy for relaxation and I was impressed. I read Vogue magazine and Mike was not impressed. On the other hand, I had a high paying IT job fighting hackers for a large bank, and Mike liked to brag about that to his friends. Mike was an accountant, and never in the history of the world has a girl told a girlfriend that she was dating an accountant and the girlfriend reacted, "Ooh, sexy!"

The bottom line? Mike was proud of his girlfriend, and I was his girlfriend. I was thrilled.

The flaw with Mike, if you can call it that, was his desire to tease other men with his girlfriend's body. That meant my body. I gave him the Dweeb treat of walking around within the apartment braless with a T shirt and panties on. I upped the ante by choosing a sheer T shirt so that he could see my boobs and nipples underneath the T shirt.

One day he sandbagged me by inviting one of his friends over when he knew I would be dressed in my 'teasing outfit' of a sheer T shirt and panties. He stood between me and the bedroom so I had nowhere to hide. I gave up and paraded around like that for his friend. His friend left with a hard on and a smile after a visit of an hour. I actually enjoyed it and remembered how much fun I had had teasing Dwoob. I even confessed I enjoyed it to Mike, and his whole face lit up.

Things escalated from there rather rapidly. He had me walking around the apartment dressed just in panties to tease the neighbors who could see me at night and in the early morning hours through the slits in our blinds, as they gapped quite a bit. We would make passionate love when we were sure someone had been checking out my 'luscious boobs,' as Mike liked to call them.

I lost it though when Mike sandbagged me a second time with the exact same friend who 'dropped in just by chance' when I was wearing only panties and nothing else. This was too much, to be 90% naked in front one of Mike's, and hence our, friends. I was furious. I acted out and stayed almost naked throughout his visit.

I took my revenge on Mike by sitting on the couch in such a way that Mike's friend, who was also a dweeb, could sit next to me on the couch if he dared. I called the friend Dwibe in my mind, since Dweeb and Dwoob were already taken. Mike called my bluff by encouraging Dwibe to sit next to me and my near naked body. He actually took it the final step and pushed Dwibe into the seat. I glared at Mike and he smiled.

Not only was I wearing only panties, but my panties were sheer. Only my pussy was hidden by thicker fabric and not even that well. It was embarrassing and humiliating. It also turned me on and that annoyed me even more.

Mike's smile was a mistake. Now I was really angry. "I see you like my boobs, Jimmy," I said. Jimmy was Dwibe's Christian name. "Do you want to touch them? Maybe fondle them a little?"

Dwibe looked right at Mike for guidance. I was his girl, after all. I said, "I can look after myself," I said. "My eyes and my boobs are over here, Jimmy."

I took his head and pulled his mouth down onto one of my nipples and held it there. Jimmy took the rather non-subtle hint and began slobbering all over my boobs as only a true dweeb can.

One more false move from Mike and I would have faked some moans. Fortunately, Mike changed his tune and hurriedly got Dwibe out of the apartment. We had our first fight. The make-up sex was wonderful. We should fight more, I thought to myself.

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byJBEdwards© 3 comments/ 5645 views/ 8 favorites

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