A lot of readers wanted to know what it's like to be Ally's boyfriend.
Well, my name is Roger and I am here to tell you all about it. I'll first give you an overview of what my (sex) life was like before I met Ally, then I'll share with you a very special story from the very beginning of our relationship.
I am a fucking loser; this is especially so, now that I am with Ally, but even before I met her, I was a loser by any measure. As a grown man, I spent an unhealthy amount of time whacking off, sucking cock and pleasuring other people, mostly men. I loved degrading, humiliating and depreciating myself in any way I liked and loved getting myself into as much trouble as I could while doing so, just for the fun of it. Although I was blessed with a huge cock, hardly anyone ever got to see it - certainly not a lot of women. Although I considered myself heterosexual, I was on my knees several times a day sucking and jerking off cocks. Why? Simple: men have the natural ability to separate sex from emotion, which makes them perfect for casual, degrading sex. Besides, there are a lot of things you can do with a cock that you can't do with a cunt: you can slap it in my face, shove it down my throat, shove it up my ass or when it's time to cum, deposit the warm gooey sperm right in the middle of my face with half inch accuracy.
Because I was too much of a wimp and a loser to have any kind of relationship before I met Ally, I used the services of call-girls on a semi-regular basis; although these girls had no real interest in me, I still went out of my way to make them think I was the biggest wanker and loser in the world. I always paid for an hour and told them they could leave as soon as I had cum. I rarely lasted longer than ten minutes; I always made sure my balls were filled to the brim and that I was horny as fuck. I almost never lasted long enough to actually penetrate her, let alone give her a good fuck. Usually a 30-second hand- or blowjob was more than enough to make me gush and sent her back on her way. The girls knew this and rarely took off their clothes anymore. They just stuffed a hand down my pants, gave me a few rough strokes and by the time they had undone my pants with their other hand, my cum was usually seeping out of my cock. Sometimes, when I was feeling particularly randy, I went one better yet and whacked myself off while the girl was still putting away the money; then she 'd just look at me with a sad smile on her face. Most girls would just fit me in on their way to a real client. The real pathetic thing was that I was usually horny again barely ten minutes later!
During college, I also manned a truck stop gloryhole every other Wednesday for almost seven months. I just sat there for about six hours, sucking every cock that got shoved through that hole, swallowing their slimy loads. Sometimes I'd get four or five, sometimes on busy nights, I'd get like twenty or twenty-five... black, white, big, small, thick, thin... I just put them in my mouth and sucked out their loads, no questions asked. I had a standing arrangement with Claire, the 59-year old, fat bathroom attendant; every other Wednesday between 7pm and 1am, the gloryhole was mine, in return for licking and eating her out at the end of her (and my) shift: a dreadfully unpleasant and humiliating experience. Because of all the cock-sucking I had been doing, I was usually sporting quite a boner and so more often than not I couldn't help myself and jerked myself off with Claire's fat legs wrapped around my head and her sordidly wet cunt rubbing up and down my face.
There, that ought to give you an idea of what a sad wanker I was, before I met Ally. To me, she was my salvation and the key to a new life. For her, I was the perfect victim for her fetish.
From the very beginning, Ally made it clear that she didn't want to get into any sort of physical relationship with me until she was completely ready for it. Although she had been sexually active with all of her former boyfriends (and quite soon too, from what she told me) I agreed to her terms. Although I was constantly hard and horny for her and she told me she masturbated almost non-stop when I wasn't with her, I respected her rules and didn't see any action for many months. Aside from a kiss on the cheek, occasionally on the lips and a warm cuddle, there was no touching of any kind: I was not allowed to see her private parts, touch her anywhere near her breasts, ass or crotch. In the fourth month of our 'going steady', our entire relationship and its future would be defined by a single incident. It was a Friday evening and Ally had been hanging around my place, my one bedroom studio apartment; studying officially, but she had spent more time in front of the TV than her books. By the end of the afternoon, there was a ring at the door. Answering the door's intercom, I learned that it was some guy looking for Ally and so I passed her on.
"Hello. Who? Nick who? Oh right. How are you? Come on up, I am in 12B. I'll buzz you in."
When she hung up the horn, she turned to me and said: "It's Nick, an old boyfriend. Can you open the door, I've gotta go freshen up."
About a minute later, there was a knock at the door. I went to open it and greeted this giant, muscular guy, who looked like he could have doubled for Stallone. I showed him into the living room, got him a beer and after we sat down, he said that he had gotten this address from Ally's parents. He was organizing some sort of high school reunion and was gathering information anyway he could; he seemed like a pretty decent fellow. Just when I thought that he was going to be a minor inconvenience, Ally walked back into the living room... I couldn't believe it: before she was wearing jeans and a t-shirt; now - after she'd gone 'freshen up' she was wearing one of her shortest black skirts, a white halter top which clearly showed her black bra underneath and about 50% of her tummy and some black stockings. My cock jumped in my pants and I knew this meant trouble. To make matters worse, after they greeted one another with a short hug, she sat down on the couch next to him, but not next to me. Nick ended up in between us and was forced to look at one of us, instead of both of us; it should come as no surprise that I quickly felt like the fifth wheel.
After about half an hour of them talking and laughing while they reminisced, only occasionally including me into the joke/conversation, I got up and said: "Another beer Nick?"
"Sure." he replied.
"And while you go and get that, I'll show Nick around the apartment." Ally said, getting up. Now, my apartment wasn't all that big; a proper tour, even with a history lesson of the entire block included, shouldn't have lasted more than three minutes at most. Still, after seven minutes they still hadn't returned; for some reason, they were lingering in the bathroom. I could hear whispering and giggling, but I couldn't make anything out. Finally, after a solid ten minutes, they walked back in, Nick first.
"Cozy little apartment." he said as he walked back towards the couch; meanwhile I could see Ally casually throwing a black bra on the dinner table as she passed by it on her way back to the couch. One glance at her top and I realized it was the bra she'd been wearing up until now! Her nipples, for some reason fully erect, were piercing through her white top like pencil erasers. She smiled wickedly as she caught me staring at her tits, now bouncing freely in her white top.
Why had she taken off her bra? Had she done so in front of him? He had probably seen them before... but had he seen them now, when Ally was supposed to be mine? Had he touched them?
All these questions and so many more rushed through my mind as my fat cock throbbed in my pants.
I did my best to stay cool about it, but truth be told I didn't quite know how to act. A few minutes later, the conversation went about Nick's car; Ally was amazed at how he was still driving the same car, and after yapping about his sports car for another couple of minutes, Nick said: "Look, I have to go get something from the car anyway; if you want, you can come and took a look at the old gal, for old time's sake."
Ally jumped at the chance and the two of them walked out to Nick's car; once again, it took them forever to get back... it must have been at least fifteen minutes before they reappeared. Ally walked in first and threw a pair of black panties and some black stockings on the dinner table, right next to her bra. As she was no longer wearing stockings, it was pretty clear that under her white top and her short black skirt, she was basically naked. Then she threw Nick's boxers - at least I assumed it were his, they certainly weren't mine - on the dinner table as well. Once again, my cock jumped in my pants: what had they been doing? Even if I imagined the most favorable scenario, there was no way Nick could have taken his boxers off without taking off his pants and that meant...
"Ally, can I talk to you for a minute?" I asked.
"Not now Roger, Nick has our high school graduation ceremony on tape."
"Can I put this in your vcr?" Nick asked, already heading towards it.
"Uhm sure." I said.