Well, She Finally Asked Me... Ch. 03

JAY: Wow. I love hearing this.

ME: Again, it happened so fast. His hand on my penis felt so good. I had always jacked off a lot at home and had been given hand jobs by girls, even had screwed a couple of girls. I started cumming all over his hand. I was barely done cumming when I thought I tasted his semen in my mouth. I tried to pull away, but he held my head with both hands keeping me there till I took it all. I had cum in my mouth and cum in my hair from his hand when he finally let go.

JAY: I'm so hard hearing about this. A boy always has to start somewhere. Then what happened?

ME: He told me he'd have to wash his sister's panties before she got back. But then he told me to put on another pair of her panties and we got high again. Walking around in front of him wearing only his sister's panties was so exciting, so naughty to be doing this with another guy. I loved that feeling of showing off my penis in his sister's panties. We looked at girlie magazines some more and he had me jack him off. Playing with his cock fascinated me. I was so hard again, after I made him cum, I jacked off in front of him. He told me nobody finds out or "everyone knows you are a queer." That night when I got home, I jacked off again because my penis was so hard thinking about what I did with him.

JAY: Fuck, that's hot. And? Was that the only time?

ME: No. I came back the next night and we did it again. He got me high again and I couldn't wait to wear his sister's panties and suck his cock. It made me harder than I'd ever been. That second night he was very nice to me, he just told me he knew I'd like it and "let's just have fun". Same thing that second night, I sucked him off and he didn't have to hold my head when he came. I knew what was expected of me and wanted to please him. Plus, wearing his sister's panties as I sucked his cock made me so fucking hard, I didn't care what I was doing. I jacked myself off as I sucked him off. I just had to taste his semen again sucking him off this second night, I was curious from the night before how it felt, making him ejaculate in my mouth. He came so hard when he came in my mouth, moaning and panting. Doing this made me so hard it was exciting to experience it again; we jacked each other off again later, it was so hot.

JAY: I could jack off right now, I'm so hard.

ME: Me too.

JAY: So then what?

ME: Since we both lived at home it was difficult to hook up like it was that time with everyone out of the house. Didn't stop me from sucking Johnny's cock some more. We'd drive out into the country, and I'd suck him off in his car. He stole some of his sister's panties from the back of her drawer that he said she'd never miss, she had so many. When I hung out with Alex, he had no idea I had been sucking his brother's cock and when I saw his hottie sister, it gave me a hard on knowing that I sucked off Johnny wearing her panties. That fall I went away to college with my secret.

JAY: If you tell me anymore, I might cum. Go ahead if you like, I love hearing about your sex life.

ME: Well, college is hard if you don't study and apply yourself and I'd always been a good student, so I did very well. Girls were hot and flirted with me. I dated a few and screwed a few, that was exciting.

JAY: What about your "secret"?

ME: By the second semester, I had the urge but didn't know how to go about it. Saw a personal ad in the college newspaper about a gay student needing help with his studies. I contacted him and told him I wasn't gay but kinda let him know I could help him out with other things besides his studies. We hooked up a few times and I kept it at that -- I sucked him off two different times but kept my clothes on. Then I felt strange, like maybe I was weird and maybe I wasn't gay. Tried not to let it bother me and just went on with school and dating girls and tried to ignore it.

JAY: Are you gay?

ME: Most likely, but I don't obsess over it.

With that we ended our chat that night and agreed to chat again soon. I was so fucking hard telling Jay all this and with Katie asleep, I pulled out a pair of panties I had hidden and had an incredibly pleasurable masturbation. When I felt gay and jacked off wearing a pair of panties as I fantasized and masturbated, it always took me to that secret place that began with Johnny. On Saturday, Katie came onto me again and we screwed. Like I'd ever turn her down. As we made love, all I could do was fantasize about the prospect of hooking up with Jay and doing very gay things with him.

With Katie being more affectionate of late, I felt a little guilty about possibly having a gay affair with Jay. ....but not so guilty that I didn't lick her pussy clean after ejaculating into her and jacking off again in front of her in my post coitus glow. Things with Jay moved along slower than I wanted them to. Maybe that was a good thing for me to be better sorted out with Katie. We had full intercourse three out of the for weekends since she saw me have sex with Kevin. Maybe I should just cool it, I thought, and not obsess about my secret that I was a closet homosexual in so many ways. It was no longer a totally a secret, and I was part way out of the closet.

Then with Katie, all of a sudden there was a change, like someone said something to her about me and she was less open, less affectionate and less sexual with me. On our usual sex day, Saturday she ignored me for sex or a hand job, we went weeks with nothing, no hand job, no screwing. She wouldn't even talk about it, so I knew something was up. I didn't press, but I was having a hard time processing being married and knowing she was having issues with my sexuality. I had a few emails with Jay but nothing dramatic or overly sexual; he was busy and had been out of town. Our acknowledgement of a renewed chat finally came to pass late one evening and Jay was very happy to connect.

JAY: Well, hello! My apologies for being out of touch. I haven't forgotten about you.

ME: Me neither.

JAY: How are things? I loved hearing what you told me so far about your life. Would you like to pick up where you left off?

ME: Things are okay. The wife has been a little chilly lately.

JAY: What's going on?

ME: Not sure. She might be having issues with my sexuality.

JAY: Does she know you might be gay?

ME: Well, that is a long story I won't get into now. She's a great gal and wonderful person, but her desire for sex and mine are at the opposite end of the spectrum. I'll tie it into my sex journey a little later.

JAY: But she knows?

ME: She's seen it. She coaxed it out of me if I'd ever sucked cock. Then she said she was okay with it if she saw me with another guy.

JAY: Women are curious when they find these things out. Go on.

ME: I told you that in college I sucked a guy off a few times but was having conflict I might be gay. With school and girls, I kind of let my secret cock sucking stay hidden, so it was way far back in my mind. I only had that one guy early in college until my last year. At times I would think about it and knew I'd have no issues sucking cock again. Then something unexpected happened, a jock I knew started hitting on me. At first, he may have been joking, but he was an assertive Alpha type, and I was obviously a beta. He did the "hey, buddy, suck my cock" routine that guys joke to other guys about. When I said "sure" and looked him straight in the eyes, it caught him off guard. We went to his apartment off campus. He was more nervous than I was. He sat on his couch, and I pulled down his sweatpants and started playing with his cock. I was very excited and hard.

JAY: Wow.

ME: It was kind of crazy, both of us had girlfriends and what we were doing was a little taboo. His cock was nice, and I pulled on it, making it very hard before I pressed my face into it. When I sunk my mouth over his cock, he squirmed and moaned and ran his fingers through my hair, saying, "fuck yeah". I was back in the place that I was with Johnny, sucking off another guy. I fucking loved sucking this guy's cock. He loved it too. When he came in my mouth, there was no doubt I was an expert cocksucker. It was a little awkward after he came, he was embarrassed and sent me on my way, but he got my phone number. I jacked off so hard when I got home that day. When I screwed my girlfriend, all I could think about was sucking cock. I got together with with this jock at least ten times before I graduated. He'd call me up and tell me to come over. That's all I ever did with him, suck his cock, he never touched me. I fell in love with his cock, loved sucking him off so much.

JAY: You're going to fall in love with my cock, Bobby.

ME: Quit teasing me.

JAY: Not teasing, just telling that you will love my cock, it's so hard for you with everything you are teIling me. I love hearing your story, go on.

ME: Well, after that it was a long time before I sucked off another guy, a couple of years. I had a roommate in an apartment, and I was working nights, and my roommate was working days. He had a hot girlfriend who left her panties in the bathroom when she stayed over. My roommate caught me jacking off in her panties and figured I was a fairy when he told me to suck his cock. He was a jerk and found it amusing that he could get me to suck his cock after that first time. He always called me a fag or a homo. I didn't live in the apartment much longer after that. Guess I was a little aimless at this time though I landed a good job and was still dating girls.

JAY: All these times you were sucking off guys, they never reciprocated or touched you?

ME: Up to this point, no. Only Johnny, in the beginning. As time went on, I would have anonymous one-time encounters sucking cock with guys I found online. Sometimes I would jack off in front of the guy after sucking him off. A couple of times a guy would help me out and give me a hand job, but no intimate contact with a guy. I always felt so dirty and ashamed of myself after sucking off a guy. I was very confused and did not want to be gay. But I loved sucking cock, it always got me off.

JAY: What changed? You're married now and seems like you really think you might be gay?

ME: Both tie in together. I saw an online ad with a guy being very direct, saying he loves guys in panties and it will make us both very happy. With him mentioning about hooking up with panties, it really appealed to me, and my guy/guy contact changed with this guy, Dan. Up to this point I was just a closet cocksucker, no other contact with guys other than sucking them off. Dan was divorced, had a nice house and invited me over to 'dress up' for him. It was surreal, laid out and waiting for me in his master bedroom he had a spaghetti strap slip dress, an array of panties, stockings, high heels, a wig, makeup in the bathroom. He told me to shower and shave, take my time and make myself at home. This was a new experience for me. I loved being in panties sucking Johnny's cock, but no one ever had any interest in me other than me getting them off.

JAY: Some men find effeminate males very desirable. I do.

ME: Like I said, it was surreal, being allowed to make myself pretty for another guy. I shaved my legs and underarms; I didn't really have much body hair anyway. Putting on stockings and panties and the dress felt divine, I was shaking with anticipation. Once I put on the wig and a little lipstick, I couldn't believe the transformation. My penis ached it was so hard being fully dressed like a woman. He'd asked me my shoe size before I came over, which I thought was odd, but once I slid into a pair of high heel strappy sandals in my stockinged feet I knew why. Not sure anything felt so sensuous and sexy. Timidly, I sauntered out to him in the living room. He was drinking a cocktail, watching TV. He stood up, admiring me, said nothing and then he kissed me. I had never kissed another man before.

JAY: You'd never kissed another man?

ME: Never. All I ever had done was suck cock. I knew the sensation of feeling feminine wearing panties and sucking cock, but nothing more.

JAY: You'd never been naked with another guy and fooled around?

ME: Nope. Guess ever since Johnny had me suck his cock; I was programmed to be the guy who sucked off other guys. I tried to get intimate with Johnny once and he pushed me away and told me to just suck his cock.

JAY: And what happened when Dan kissed you?

ME: OMG, it was like fireworks were going off inside me. Being in a dress, heels, panties and a wig and being kissed, being the girl, being desired as feminine, it was a sensation so wonderful I thought I would lose my mind. Kissing him as he fondled me through the dress was driving me crazy. When he snuck his hands inside my panties and fondled my penis it felt so good, I'd rarely had a guy touch me before.

JAY: Lovely...

ME: Instinctively, I dropped to my knees and tried to open his pants. He stopped me, pulled me up and said, "let's go make love, sweetie". We went to his bedroom, and I helped him out of his clothes, and we were all over each other. It was so erotic. I guess I was not expecting what happened, I just thought I was going to go over to his place, put on panties and suck his cock. This was so much better. We kissed madly, hungrily, passionately like lovers. It was a strange and wonderful experience kissing and being with a naked man.

JAY: Did you enjoy it?

ME: Enjoy it? It was about the most exciting sex I had ever had. I ended up in bed with me just wearing panties, stockings and high heels. He pulled off the wig and told me I was the loveliest homosexual he had ever seen. We sucked on each other's cocks, I never had another guy suck my cock, it was wonderful, so different than a girl doing it.

JAY: What happened? Did he try to penetrate you.

ME: He was so kind and loving. I jacked off as I sucked him off. When he came in my mouth, I ejaculated all over myself. And then he lovingly licked up all my semen and fed it back to me kissing me. It was like a dream. I spent the night with him in his bed, I felt like I was his girlfriend. He didn't try to screw me right away, we just had wonderful sex all weekend. His cock was always hard for me.

JAY: My cock is hard for you Bobby.

ME: Stop teasing. You have no idea how much I want to act the same towards you as I did with Dan. I'm not even sure you like effeminate acting guys like me.

JAY: Let me tell you this, Bobby. I was married once also and beta boys like you are the reason I am divorced. I love hearing about you and Dan. Did he ever try to screw you?

ME: Like I said, it was surreal. It was a culmination of my closet cock sucking to have only been sucking guys off but never having full sex with them. With Dan, it was a sexual dream world, he made me feel so sexual and desired, it was so new and intoxicating. We spent the whole weekend together; Friday night, all of Saturday and most of Sunday. I was in panties and lingerie the whole time, even tried on some of his ex-wife's dresses.

JAY: And he didn't try to screw you?

ME: He told me he wanted to, but he was very kind and not pushy. He made it fun. With me acting like a fairy fag, it was fun. He loved kissing me and playing with my penis. He called me his girlfriend. I had never had another guy lick my balls and penis, suck my cock. It felt so good. When he licked my tight hole, I'm not sure anything had ever felt so good. I squirmed as his warm wet tongue invaded my tender butthole; it made me lose my mind. He pressed his cock against my hole, but I told him to stop, that I was not ready. He was cool about it and said to let me know when I was ready, that I would really like it. I was so horny from him licking my butt that I sucked him off like a wild child. It was like I could not get enough of the taste of his cock and the taste of his semen. After he came in my mouth, I was so fucking hard being naked in bed with him, all I had on was stockings and a half camisole. Dan started masturbating me and then he pulled out a vibrator and said, "let's try this". He lubed it up and slowly worked it up my butt.

JAY: Did you like that?

ME: It felt strange, but it felt fantastic. He let me push it in and out as he jacked me off. It was embarrassing how good it felt when I came.

JAY: Bobby, I so hard hearing all this. I still can't figure out how you married a beautiful woman, yet you sound pretty gay to me.

ME: I'll try to explain. After that first weekend with Dan, I was a nervous wreck. I was freaking out that I was gay and all the ramifications about that after being viewed as straight by everyone my whole life.

JAY: What happened to you and Dan?

ME: He invited me over the next weekend, but I was nervous about turning gay. It was one thing to be gay, but to be a femme fairy princess for another guy, that's not something you want other people to know. And a fair amount of people that I knew spoke very disparagingly about gay and trans people. I had always done a good job staying well hidden in the closet. I did go back over to Dan's that weekend and it was every bit as exciting as the first weekend. Dan was so fun to be with and he made me feel special to be femme and gay, it was a whole new world. No sex I had ever experienced was as exciting as it was with Dan. It was beyond thrilling. The minute I got in the door we were all over each other and I was in panties kissing him and sucking his cock. Just being able to have our private sex world in the closet made any sex with a girl or me sucking off guys seem tame. I was acting like such a fairy.

JAY: I don't understand then, about you and your wife. Everything you have told me make you seem flat out gay.

ME: Maybe I am, I guess. But it's not easy being perceived as straight all your life and coming to grips with it. I've never once thought about coming out, except maybe lately. Still, being a closet homosexual is an exciting secret to have, especially when the sex was so great that Dan and I were having.

JAY: So, what happened? What changed?

ME: You asked if Dan ever screwed me, yes, he did. The first few times it started out a little painful and I had him stop. I'd taken one of his vibrators home with me and practiced with it jacking off. By the third time he tried to screw me, it was fantastic. I'd always felt so feminine wearing panties and sucking cock but by this time I really was becoming his girlfriend. He made love to me like I was a girl, and his cock was always so hard for me whether I was sucking it, or he was fucking me. Maybe it was too much, too soon and he was so infatuated with me and was really coming on strong. He started telling me "I love you," I was beginning to get scared that I really was gay and might be outed. I'd been spending every weekend with him for about two months, sometimes I'd even go over after work during the week and suck him off. I loved sucking his cock so much. Maybe doing that was leading him on.

JAY: And?

ME: As much as I loved the sex, I was conflicted about the romance part and didn't want to face the fact I might be gay. I told him one weekend that I couldn't come over just to see what it was like not being his girl. Dan was crushed, and I was a wreck of guilt the whole weekend. I made it up to him the next weekend and the sex was beyond fantastic, except....on Sunday morning after we had just made wonderful love with him fucking the daylights out of me, he gave me a "promise ring". He asked me to move in with him and that I should quit my job, that he had enough money to take care of me.

JAY: Many men would love to have a "boy wife". Pretty nice thought in my book. And then what happened?

ME: Well, as much as I loved the sex, it literally scared me straight and I broke it off with him. And as fate would have it, I had known Katie from before my time with Dan. I think I asked her out once before being with Dan, but she turned me down, but was nice about it. After I broke up with Dan, I ran into Katie a few times and she was very nice to me, I wasn't expecting that at all. Out of the blue, I asked her out and she accepted. She made a silly comment like "I'm so glad, I was afraid you might be gay." She had no idea. It started slowly but we dated for over two years before I asked her to marry me. The sex started out slowly as well, it was several months before she let me screw her. Not like with guys who go straight to the chase....