Jessica's Brother

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.

There really was quite a bit of dread hanging over me from agreeing to date Chris and the embarrassment that I had just jacked off in her panties. But none of that prevented me, not even two hours later, from taking off my clothes, pulling out the girlie magazines and the damp semen-soaked panties. The scent of damp semen on the panties sent my arousal as high as it was from the earlier masturbation, only sooner. Now it was an obsession. I quickly found another slender hottie in a Playboy; the girls in Playboy were classier, and sexy, less crude, but the spreads were also shorter. None of that mattered, it was the scent of the semen on the panties and the anticipation that I was going gay, dating another guy, that peaked my arousal.

My penis was so fucking hard, I was embarrassed and ashamed that I was jacking off again to the aroma of Jessica's semen-soaked panties knowing that the next time I had sex with another person it would likely be gay sex with another guy. This was an obsessive, frantic masturbation, like I couldn't help myself, not being able to control my urges. Shouldn't have to admit it, but guessing that being a beta, something in your psychological makeup wills you to be a chronic, compulsive masturbator and women pick up on that, leading to an endless cycle of masturbation and less than meaningful relationships. It was not as if I could stop right then with my hard dick in my hand, the scent of damp semen in my nostrils and an as yet, unknown horizon of homosexuality blocking out everything else.

Jacking off with this myriad of emotions and stimuli, I set the panties aside for a moment and began to finger myself with my other hand. This was another pleasure that scared me, especially when I succumbed to my urges and put a lubricated taper candle or round brush handle up my butt while masturbating. Can't tell you when or why that started, but I enjoyed it so much, that I rarely did it out of shame. But that didn't mean I didn't enjoy it. I had some mind-boggling ejaculations with something like that up my butt, yet as soon as I ejaculated, I tried to ignore that I even did it. Now I was too close to cumming to find something for up my butt, so fingering myself and jacking off would have to do.

Not even sure this second beat off session took any longer, might have been quicker as I was so aroused by what was going on in my mind and my body. When I pulled on the damp panties up over my aching, embarrassed penis, the way they felt, damp and naughty, I jacked off so hard it nearly hurt as I splashed myself again with my semen. Was not quite as much semen as before but the ejaculation was every bit as powerful and exciting, though I came back to earth quicker and was many times more ashamed of myself as I took off the panties and sopped up the semen with them once again.

Then, as the day wore on, the anticipation and anxiety ate at me. Would Chris call? When would he call? What would he say? What would I say? What would he tell Jessica? Why did I tell Jess that it was 'okay' to date her brother? Would I chicken out? I could just not answer the phone and be a real pussy about it. What if he didn't call today or tomorrow or in three days and I'd be in agony not knowing? What if he called when I was with someone and couldn't talk?

Just then, in the early evening, as I was driving myself crazy with anxiety, the phone did ring. I froze. A chilling shiver of fear ran down my spine as I reached for my phone.

"Hello," I answered, trying to maintain.

"Hi Bobby, this is Chris," he spoke. "I know this is awkward. Guessing Jessica spoke to you?"

"Yes, she told me this morning," I said trying to sound composed, which I wasn't.

"I hope you're okay with this. I've always thought you were very nice and now it seems okay to try and get to know you," he went on. "Jessica's loss is our gain," Chris told me, trying to break the ice and get around the fact of me dating Jess.

"I'm not sure exactly what to say or how to handle this, but I am flattered," I told Chris.

Deep down, I was flattered that someone was interested in me, even if it was another guy. Truth of the matter was, that if Jessica was a hottie, and she was, then Chris was every bit as hot on the masculine side - six one, 185, dark eyes and short hair, clean cut and athletic. Maybe he was attracted to skinny shorter guys like my five foot eight, 145.

"We can take it slow; I want you to be okay with this. If you're not, just say so, I understand, and we can let it go. We can still be friends," Chris told me.

"I'm glad you called," I told him.

What I didn't tell him was that my penis was so fucking hard talking to him. It was strange that I was more excited about the prospect of hooking up with him than all the times with Jess and the constant doubt I had about where I stood in my relationship with her.

"Jess told me to wait three days before calling you to make you sweat it out, to see if you'd chicken out. I think I'm better for you than she was. She can be such a bitch to the guys she dates. Playing with their heads is sport with her."

"Talking with you seems much easier and natural than it did with her," I said, my penis incredibly hard at the thought of seeing him naked and him seeing me naked. "I'm okay with you calling. I was scared and shocked at first. Now it seems exciting."

It was exciting. We made arrangements to meet for pizza at a place by the campus on Friday night. By the time we got off the phone, I had but one mission, to beat off again. During my time dating Jessica, I admit that I jacked off as much as when I wasn't dating anyone.

She gave it up so little and was such a tease holding me at bay, that my masturbation habits remained unchanged. Now I was preparing to beat off for the third time that day, not uncommon in my world.

While yes, I was a masturbator, I wasn't well versed on gay porn. I'd always skip by quickly if any gay stuff showed up on the sites I'd wank too. Didn't want to mess up my phone or laptop with junk, so I was content with girlie magazines for the most part, though I'd have to admit I loved teen girls in porn videos. I tried not to like it, but there was a video with two teen guys and a girl in a bikini by the pool. It was hot seeing her take off her top and the boys playing with her breasts as she rubbed their cocks through their trunks. They went inside and while they mainly played with her, but I didn't look away when they played with each other's cocks, kissed each other or took turns sucking each other's cocks. And in the Penthouse's, it was common to see guys with big hard cocks cumming on chicks, so that made it okay to look.

In bed with my laptop, the gay porn was way too over the top hard core. Big hairy muscular guys having sex was not doing anything for me. When I clicked a "twink" link, then a light went on. I identified with slender, smooth, hairless young men kissing and sucking cock. I was slender, smooth and mostly hairless. It all looked so natural and loving, it gave me a charge. The whole day was a blur from the moment Jess told me about her brother's interest in me. Now I was masturbating for the third time because of what she told me and now setting up a gay date with another guy, Chris. I had denied myself permission to view gay porn; now that it was out in the open, I allowed myself to enjoy it. I couldn't believe that I had denied myself for so long it was giving me such a thrill.

Images and videos of boys having sex with each other was fascinating. Maybe I was gay the whole time and did not realize it. Seeing boys kiss as they screwed missionary style really sent me. This gave me permission to grab that slender taper candle and some Vaseline. When I saw some pics of a fem boy in panties having sex with a more masculine boy, I knew why jacking off in Jessica's panties felt so good. Jessica's cute string bikini panties were still slightly damp from the semen discharges I sopped up with them from my previous two masturbations I had earlier. It was now okay to take a heady sniff of the damp semen on Jess's panties. Fucking really loved that erotic scent of damp semen on girly panties. I set the lubricated taper candle on the nightstand and pulled on the slightly damp semen-soaked panties once more, gawd they felt incredible.

Relishing the sensation of the panties on my penis and the implication that I was gay, made my penis incredibly hard and exited. The endorphins of sex and arousal were exploding within my mind and body now that I accepted that I was "going gay". This was a more relaxed, sensuous masturbation than the frantic two earlier beat offs, and I submersed myself into a wonderland of gay twink porn, with the added element of Jess's panties hugging my penis. Taking off the panties, I took another long whiff of their damp semen scent and perhaps what little of Jess's pussy aroma remained.

Spreading my legs and lifting up my bottom, I inserted the greased tapered candle up my butt. It felt so chilling and naughty, yet so right as the twin stimulation of something violating my butt and me stroking my penis urging me on. I wondered what it would be like if Chris screwed me. Inside my arousal, I had zero interest in screwing another guy, but the thought of getting screwed myself, especially with the sensation of something now up my butt, made this masturbation fabulous. I was writhing all over the bed in arousal I was so horny. By the time I ejaculated, my mind was going high speed fantasy about being gay with Chris.

Naturally, I was a little nervous meeting Chriss at the pizza shop, but there was no anxiety, just curiosity. I had showered and shaved and wore something that I felt comfortable in. We had pizza and beer with polite small talk and for me, the anticipation that I was on a 'date' with another guy. No one else knew that we were on a date, just two guys having beer and pizza, right? I knew. After eating, we went to a nearby game arcade and played some air hockey. Chris and I enjoyed the competition, and I took four games out of seven. Up to this point there had been no contact touching each other.

There was a park nearby and we walked around, saying little as it was getting dark. When Chris took my hand, I knew. I knew the sensation was more relaxed and exciting than how I felt with Jess. She made me feel like she was just putting up with me, that there was something always more important around than me being with her. It was beyond exciting holding hands with Chris, I got a hard on the minute we joined hands. Chris led me to a tree behind a park bench. I couldn't believe what was happening, I was kissing another guy. Kissing Jessica's brother, wow, I was in a daze.

It was a fabulous feeling that I never thought about it happening and never knew it would turn me on so much. Wasn't being gay just about sucking cock and such? Oh, fuck, this was so hot. It was so new, so taboo, so erotic, two guys kissing after dark behind a tree in the park. We were both so hard, groping each other as we were kissing, feeling each other's hard ons. It was frantic, breathless making out, magnetic, like we'd been waiting all our lives for this, so glad to be connecting. When the first round of kisses finally broke, we were still nuzzling faces together, hot breath in ears and necks.

"You're so hot," Chris told me. "I've wanted you for so long."

Wow. That made me even harder as a new round of kissing, necking and groping began. Feeling his cock through his jeans was amazing and it made my own so very hard. We held each other in wonderment when Chris asked me if I wanted to meet him at his place. Once we got there, after some initial kissing right inside the door, we took turns peeing and ended up on the couch, holding hands and grinning. Chris fired up a bowl after pouring some wine as this surreal gay date continued. Getting high always made me so horny. It was just a few days ago that Jess broke it to me that Chris wanted to go out with me, I had no idea I'd be in this situation. But I fucking loved it, I loved how exciting being gay with another guy made me feel. We couldn't keep our hands off each other and continued kissing and feeling each other's cocks through our pants. I climbed on top of him, kissing him, nuzzling faces together, aroused and horny beyond anything I ever felt with Jessica.

"We don't have to go slow," I told Chris as I rubbed his cock through his jeans.

I bit him on the ear, and he whispered, "I want you". That's all it took as he pulled me up, we kissed madly by the couch, and he led me to his bedroom. In a frantic rush, we kissed and helped each other out of our clothes. We stood naked by the bed, kissing and pulling on each other's massively hard erections. Climbing into bed naked with another guy was the most exciting sexual thing I had ever done. Male scent on male scent. Male skin on male skin. Two hard cocks pressing into each other's bodies as we rolled around, nuzzling, kissing each other madly, stroking pulling touching cocks in wild breathless abandon. When I slipped Chris's beautiful hard cock between my lips and started sucking his cock, I knew I was gay. It tasted so fucking good and the sensation it gave my own penis was driving me mad with homosexual lust. Fuck Jessica, bitch. This was so much hotter, so much more passionate than one minute I spent naked with her.