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A Tale of Two Bobs

In high school I was in love with a guy named Bob. Not exactly the name you expect at the end of that sentence, right? I thought about changing it to something else, but sometimes reality is better than fiction. Love might be a stretch in this particular situation, but that is how I felt at the tender age of fourteen, before I knew what it meant to really know someone and love them. If anything, he was my very own Ethan Hawk in Reality Bites, Christian Slater in Pump Up The Volume and Jared Leto in My So-Called Life. He was all of those things and none of them by virtue of not being a real person I could connect with, but oh boy did that not stop me from liking the hell out of him. 

The night I had my first date with the guy, he had asked out a handful of other girls before landing on me. I knew it and I didn’t give a shit. In fact, it didn’t make me feel devalued as a person even though it probably should have. I was enthralled and utterly inexperienced. My friend Alex was on a date with his best friend, another Bob, and we all sat together at the movie theatre. Don’t ask me what was playing, I don’t even think I was aware of it at the time. All I was conscious of was his presence next to mine and what would happen next. I had only kissed one boy before that night and that was the limit of my sexual experience. 

The two Bob’s sat side by side with Alex and I on either end. My Bob, for the evening, took my hand in his and placed it on his leg. I don’t think my body ever felt as tense as it did in that moment. I might have been enthralled by the guy, but I wasn’t naive either. I did know that I was only one in a string of girls he would have gladly went out with that night in the hopes of getting some action, and even though I had said yes, there was no way I was going to fall for it that easily. So, it didn’t come as a surprise that every so often his hand would slid my hand just a little bit further up his thigh. In fact, I was kind of amused by the whole thing. I let him do it, observing just how long it would take him to bring my hand to the brink. I was also trying to think of a way of getting myself out of this sticky situation. 

As you would have it neither of those things would happen. Alex’s Bob indicated that they should leave, obviously the first part of the evening was over and they had other things to do and most probably more experienced girls to play around with, but before vacating his seat my Bob turned towards me and kissed me. Let me tell you, I’ve kissed a lot of people since then and it still counts as one of the top five kisses I’ve ever experienced. Next thing I knew, he was standing in the aisle getting ready to leave and giving me his number. A number that I would remember by heart for the remainder of high school. 

Later on, the second Bob would tell me that my Bob had said I had the sweetest softest tongue he had ever kissed, but as you can imagine things didn’t exactly turn out all fairy tale like. Over the next few months, Bob number one would ask me out again and to Bob number two’s surprise I would say yes. Only to invariably find myself stood up, which didn’t stop me from feeling electricity going up my spine every time he would pay attention to me. It kind of went on like this for months, he would ignore me, then pay special attention to me like he had suddenly realized that I truly blew his mind and then something would sort of happen between us and then he would resume to ignoring me. 

Time passed, I eventually lost my virginity to someone else the summer I was fifteen, and then one that winter on a random Tuesday night, I decided I had enough of all of this pussy footing around with Bob number one and I made it my mission to get him into bed. I used the oh-so-well memorized phone number and called him from a pay phone to make things happen. Bob number two happened to be over at his house that night and he was the one to answer the phone. He teased me and sort of gave me a hard time when I asked for Bob number one, coyly asking me why I wanted to talk to him. To which my brave little soul answered “take a guess” in the kind of tone that left no room for guessing. 

I got my invitation and walked my ass over to his house on that cold winter night. I still remember what I was wearing, if you can believe it, my best friend’s light blue denim bell bottoms, doc martens, a pair of blue underwear that did not match my blue bra, a yellow t-shirt featuring a list of Diver’s excuses (the shirt deserves an explanation of its own, maybe next time) and what passed for a winter jacket. Once inside, I sat on the couch next to Bob number one while Bob number two sat on the lazy boy next to us. Even though I had already made my intentions rather clear that didn’t stop them from plying me with alcohol. 

They were quite a pair. Innuendoes and hushed messages were flying all over the place. Even the music that they played held a meaning. Two songs in particular come to mind: You Can’t Always Get What You Want by The Rolling Stones and She Asked For It by Hole. Just look up the lyrics and imagine how ridiculous the scene might have been. They played them just for me, to get the message across. Eventually, Bob number two left us alone to get more beer at the store. Bob number one and I looked at each other on the couch, waiting to see what the other would do, all we could say to each other was “what do you want to do?”, which would prompt the other to ask the exact same question. The second of third time the question bounced back to me, I simply said “How about fucking?” Three little words that probably had a lot to do with forging my reputation as a slut regardless of the fact that this would be the second time I would ever have sex. 

I think he was a little taken aback with such a direct question, but he was not one to stammer under pressure. He took my hand and led me downstairs to his bedroom. Feeling a little awkward and wanting to stay in control, I asked him if he had a condom. A redundant question in my mind at least since I knew I had one in my back pocket. Always be prepared was my motto, I paid attention in sex ed class. We walked into his bedroom, it was dark as hell in there, I could barely see the bed. We were both in our knees facing each other, kissing and pressing our bodies against one another. He had a rather large cock, and it was hard as rock, pressing against his jeans and the palm of my hand. That’s how I like to remember him. 

The rest takes a turn for the worse. I could still hear the tape that was playing upstairs, Black Sabbath’s We Sold Our Soul For Rocking Roll filtering into the room through the ceiling while I laid on my back and he turned to his side to grab a rubber from the side table and slide it down his cock. I knew that Bob number two was back because I heard him flip the tape over as his friend, my Bob slide into me. I remember he told me to slow down, because I was grinding too fast, he told me “not yet”, and while he was pounding away I couldn’t help but think “I love him, shouldn’t I be feeling something more instead of wondering why I’m not?” Soon enough though, and before I could come up with an answer he came and pulled out of me. I might have paid attention in sex ed class, but they failed to mention that you should always make sure the guy actually puts the condom on and doesn’t just pretend to. 

My thighs were wet and sticky with his cum, confused and ensure of myself, I asked him if he had put a condom on. He said he did, but the wet spot I felt on the sheet when I brushed my hand against the top of the bed told another story. Seeing I wasn’t convinced he told me “it doesn’t matter, I didn’t cum inside of you”. I might have been inexperienced, but I hadn’t cum and the juices flowing out of me weren’t mine. I left it at that, didn’t add another word. No one would get away with something like that now, but it took me a while to process what had just happened.

I pushed it all aside for the moment and followed him upstairs where he took a seat on the lazy boy and I resumed my seat on the couch with Bob number two as my partner in crime. Maybe, reading this you saw it coming before I did at the time, but it didn’t take long for the innuendoes to start up again, only this time Bob number one was making them and they were directed towards me and Bob number two. I was young and I was hammered, but I knew without a doubt what was going through their minds…

Stay tuned for A Tale of Two Bob’s: The Sequel coming to a blog near you next Sunday. 

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3 Responses

  1. Domina Doll says:

    Awesome Olga! Can’t wait for the sequel!

    Your story reminds me of this guy I had a huge crush on in Junior High. All my GFs had gone out with him and finally it came my turn. I was at his house, in his bedroom with his mother home (I guess she was used to him bringing girls home into his bedroom). I thought because she was there he would try anything one me but was wrong. Our necking lead to groping which lead to zippers unzippings and tops flying off. We were laying half-nakid under a blanket and he was hard and trying to get my pants on. Suddenly, I got cold feet and said I had to pee. Ofcourse, I had to get all dressed again and when I came back form the bathroom he was pissed.

    Not the first guy I gave blue balls to LOL. Not sure why I didn’t want to go through with it with him. He would have been my 2nd fuck, so I wasn’t a virgin. But, somehow I didn’t just want to be another notch in his belt. Afterwards, I lost respect for him and he was no longer my crush…

    This story is nothing like yours but somehow yours reminded me of him…

    • I can see why my story reminded you of him though. There’s a similar vibe. Before the night I did go through with it and have sex with him, there was a similar evening spent in his bed while his mom was home. Only I was still a virgin at the time and I was on my period. He thought I was lying and that I was just trying to cock block him or whatever. Anyway, that whole scene kind of killed the mood and I went home.

  1. April 4, 2010

    […] This post was mentioned on Twitter by dominadoll, Olga Wolstenholme. Olga Wolstenholme said: A Tale of Two Bobs […]

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