How do you handle it when your ex-girlfriend tells you that her brother wants to date you? I was beyond shocked by this, but at the same time it was both an exciting and a scary thing that I felt. Jessica and I were dating just under a year, but it really wasn't going anywhere, and I always felt like I was being pulled around on a string by her. Guessing I was the beta in the relationship, as whatever we did, it was always what Jess wanted or didn't want. She did let me screw her a few times, maybe five times in about a year. She lived at home and never once spent the night at my apartment. It was great sex for me, but I'm not sure it moved her needle one way or the other. I was just happy to get lucky now and then, so, as often is the case with girls and beta guys, it's easy to dump them. And dump me she did, but nicely, you know, the "friend zone" kinda thing.
Jess and I were still friendly when we ran into each other. I'll admit, it was unsettling when she told me of her brother's interest in me when we had coffee together that day after class. I'd met Chris several times over at her house, but he was older by about five years and Jess never said anything about him being gay.
Again, being a beta and being told by your ex-girlfriend that her gay brother wants to date you is sobering. Maybe it's humiliating, because she's insinuating that you are not manly enough for a hottie like her, but she views you as a queer? If my self-confidence with women was low before she told me this, it was then crushed under foot like a tossed cigarette butt.
My response was a total "deer in the headlights" look and I was unable to answer as a jumble of thoughts and apprehension floored me. I think she really, really enjoyed telling me this about her brother and found pleasure in my squirming discomfort. Think about it. I was allowed to have sex with her those few times, driving me crazy with sexual excitement, but it did not do much for her. I loved seeing her naked, playing with her pretty little titties, licking her pussy and screwing her, but I was not good enough for her, yet she thought I would be perfect for her gay brother.
"Can I have Chris call you?" she asked.
As she asked this, I was still having trouble grasping the enormity of what she was talking about. The strange thing was that when she asked that, I got a huge hard on. It's not like I consciously thought about being gay, but with Jess making it seem okay, that changed my life, then and there.
Like any guy, well I'm guessing us beta guys, the thought of wondering what it would be like to have sex with another guy has passed our minds more than just once. Sure, in formative years, there was some fooling around with guys, but nothing to turn me gay.
So having it laid out for you to try, without having to think too much about it and then chickening out, not having to make a conscious the effort to seek a gay encounter on your own, where you'd worry about it or feel guilty about it, then maybe it was meant to be with Jessica asking me about this.
When I mumbled out a shy "okay", Jess lit up, grabbed my arm and said, "this is so exciting". I guess I felt flattered, like a girl, with Chris wanting to call me. So many things were going through my mind.
When I got back to my apartment, I went straight to my bed and took off my clothes. The tingly feeling in my penis, made it harder than it ever had been. I pulled out a stack of old Playboys and Penthouses that I got at a flea market. If I jacked off to hottie naked women, then maybe I was not gay after all. Not really sure how to explain this, but there was one girl in one of the Penthouses that I loved more than any of the other girls. She was slender with beautiful, perfect little titties, a lot like Jessica, not the overly huge ugly breasts like many of the other women. She seemed sweeter and nice, not a skank like a lot of the other women in some girlie mags. I had been masturbating to this pretty girl in Penthouse long before I started dating Jessica.
I felt so nervous, naughty and guilty jacking off to this girl in the magazine yet knowing I had accepted to go on a gay date with Jess's brother. It was like "what are you doing?", "what were you thinking?", "why did you tell Jess 'Okay' to date her brother?" Yet the thought that her brother was interested in me made my penis as hard as it ever had been. Then I remembered something. One of the few times that I ever screwed Jessica, a couple of weeks ago, she had left a pair of her panties on the floor after we screwed, forgot them and never asked for them back. I just stuck them in the back of my dresser and didn't think much of it. It was not like I was going to have the nerve or the opportunity to see if she wanted them back.
These panties were just simple cotton string bikini panties with little flowers on them. I'd never given them a second thought, guessing that I was too much of a pussy to 'molest' her underwear. My penis was so fucking hard when I pulled them out. The whole conundrum of Jess and her brother, me jacking off to the girlie magazines and now sneaking her panties made my arousal as naughty and exciting, higher than I had ever been in sexual stimulation. That was until I made the mistake and took a whiff of the soiled panel of her panties. It still had a rather noticeable scent of her femininity.
By the time I crawled back in bed and pulled the panties up my legs over my aching erection, time stood still, there naked on top of my bed. My penis had never been that hard and I had never felt that level of arousal pulsating through my penis and my mind. Then, from time standing still, to everything spinning in a whirlwind of excitement, I masturbated fiercely to the naughty sensation of wearing Jess's panties, looking at the naked girl in the magazine and the die cast that I was going to be asked on a gay date with another guy. What if Chris called while I was jacking off?
Wearing Jessica's panties while I jacked off made me feel gay. It was the connection that she thought I should date her brother and be gay, this emasculated me in my mind by putting on her panties. Feeling the loveliness wearing her panties on my stiff, excited penis as I masturbated wildly to the sensation, was a pretty good indication of me embracing gayness. Literally, I was bucking and flailing as I jacked off, urging arousal, pleasure and relief from my penis as I huffed and moaned, ejaculating brisk jets of semen all over my tummy and chest, some cum even reaching under my chin. It took a while to come down from this high and back to reality, a reality that I was sopped with semen all over myself and the reality that I still had to deal with my acceptance of crossing over into homosexuality.
My penis still tingled as it softened, and I tried to take stock in the wetness and scent of semen all over myself and how was I going to handle it if Chris called. I took the panties off, and with them I absentmindedly sopped up the semen that had puddled upon my body. When I took a quick whiff of the damp semen on the panties, I felt like a pervert as the tangy scent of semen reminded me that I had just masturbated wearing my ex-girlfriend's panties and that she thought it was "exciting" that I agreed to 'go gay' and date her brother.
