Under the Gaze of the Sirens 04: The Gay Chat Line

Emasculation tales continue. A very strange love affair?

It was not all that long ago. The gay chat line, you call in to hook up for phone sex or real hook ups if the other guy was close enough. I was living with a straight roommate in a funky old apartment building. Our apartment was on the ground floor, but it had a basement with a rec room, bathroom and two bedrooms where I stayed in one and my roommate lived upstairs on the ground floor in the master bedroom. I always had girlfriends off and on after my divorce, but sex with other guys was easier yet not always that satisfying for anonymous sex.

My sex drive was off the charts, and I would call the chat line any hour of the day even if my roommate was home. One night it was about six pm and I hooked up a chat with a guy and he asked where I was in town (this was in Denver, a big city). I told him Littleton and he asked if I wanted to meet him at a bar a few blocks from me. We met after I walked over, and we talked a little bit in the bar. He seemed like a nice guy; I invited him over and he drove me home. The basement apartment where I lived had a door to an outdoor breezeway leading to a common laundry room. I told this guy, Dave, to go around there and I'd let him in, so my straight roommate who was home would not know about us hooking up.

Right after I let this guy in from the outside basement door, I got a phone call from Deb, my girlfriend. Well, she used to be my girlfriend, but after we broke up, she'd brush me off every time I'd try to contact her. I had not heard from her in many, many months. This was an irony as we had been apart for quite some time though I always sent out feelers to her, I never heard back from her. So, right as I sneak a guy I'm hooking up with into my room, she calls? Yeah, a little weird. The guy was cool about it and waited nearly fifteen minutes till I finally got off the phone with Deb. Then we immediately joined and started kissing. A gay hook up is often a frenzy of arousal in the excitement of discovering a new homosexual lover, and with Dave it was just one of those magical moments. We stopped our hungry gay kisses long enough to disrobe. After all the unfulfilling, strange, sometimes forced, sometimes scary anonymous gay encounters I had done up to this point, this turned out to be one of the best gay hookups in my life.

During this encounter I had with Dave at that old apartment, it was very sensuous, we kissed and nuzzled; it was electric, and we really hit it off with each other. We rolled around naked kissing and playing with each other's cocks, we sucked on each other's cocks till he lay back and I took him in my mouth. In quiet determination I went down on him as he was sprawled across my bed. With his cock in my mouth, I lovingly sucked him off till he ejaculated in my mouth. I sucked down every drop of semen from his cock, then bathed his cock and balls with my mouth and tongue. It was the best blow job I had ever given anyone. He was cool, handsome with short dark hair and he really dug me, said I was hot. I was so horny and hard and hadn't cum yet. Dave and I just kissed, nuzzled and whispered loving things for quite some time, he loved my cock and sucked on my cock some more. Must have been about an hour of this since I had sucked him off and he was hard again as we frotted and played with each other's cocks. I put a condom on him and climbed on top of him and he pretty much slid right in. We fucked with me on top kissing him till he came again, and I finally came.

As he was dressing and getting ready to leave, I had some lingerie catalogs laying on the floor, I told him I wanted to be like that for him. Dave smiled and told me I was a doll, a dreamboat. He said he thought I was a hot guy just as I am but was cool and understood if I wanted to act femme around him. Told me that femme guys are sexy and are the most sensuous lovers. He was happy to give me his phone number and from there my life began to change. I felt like a teenage girl when Dave and I started dating.

Every time we saw each other it was a wonderful rush to be together. Dating another guy was an exciting secret I hid from my straight roommate, from my family, from my friends and coworkers. After being married and dating girls all my life it was a wonderful world of discovery, dating another guy. It was the most exciting relationship I had ever had with anyone; I was smitten with the stimulation of having a steady, romantic relationship with another guy. It was beyond exciting; I was hard all the time when I was not around him and when I was able to show up at his place, fireworks went off the moment I walked in his door.

The fact I could meet Dave at his place and not have to hide it from my straight roommate made it easy and fun for me. Sometimes if we both had the afternoon off, I'd be over at Dave's, he'd be naked in bed waiting for me as I would let myself in and take my clothes off next to his bed and climb in bed with him. Being naked and hard in bed with him was more exciting than any sex I ever had with a girl. Dave and I kissed like the sex crazed lovers we were; rubbing, frotting, pulling on each other's cocks, sucking cock, homosexual sixty-nine. His cock was nice, big, awesome helmet head, always hard for me. I loved sucking his big hairy cock, could not believe what a cock sucker I had become, how much I loved sucking dick, Dave's dick, and sucking him off, making him cum in my mouth.

I was addicted to his cock, a fag for his cock. Dave told me he was not sure anyone had ever sucked his cock as better than me. It was decadently delicious gay sex, two very horny handsome guys naked in bed all the time, never tiring of getting each other off. Truth be known I was naturally a bottom and with Dave telling me he was clean, and I was the only guy he was seeing, this made bareback sex with him incredible. I loved getting fucked, I was such a willing, horny, insatiable bottom for cock. We really got along well and had lots of fun together besides the incredible gay sex, it was bordering on romance. I had no idea how fucking wonderful it was having a steady gay boyfriend.

My gayness with Dave blossomed and I began to act out with him what I always felt inside, being faggy and effeminate. Being his gay boyfriend gave me an incredible sense of femininity, so much so, that not too much to Dave's surprise I started wearing panties and stockings to bed with him. Becoming more and more effeminate, it was not uncommon for me to wear panties and a bra or bustier along with high heels and lipstick and makeup. The sensation it gave me, being free to be girly and act feminine, accelerated my sense of gayness. Jokingly, Dave told me I fucked like a girl. I loved spreading my legs and getting fucked like a girl. Dave would lick my boy pussy before fucking me, sending me into fits of excruciating pleasure as his tongue molested my tender tight hole.

In my straight life at work and with my roommate I tried to maintain and not let it show how faggy I had become. I'd spend the night over at Dave's two or three nights a week and my roommate eventually asked if I had a girlfriend. Lying, I told him I was seeing a divorced gal on the other side of town. Then an event happened that would change everything and change it for the better. The apartment building that I was living in was being sold and since our apartment was the original caretakers/manager's apartment we were getting kicked out so the new owners could live there. It was kind of a hectic time, and I told my straight roommate I had found a place to live, and he was on his own.

My old roommate had no need to know that Dave had asked me to move in with him. Dave and I were ecstatic. Dave had been out for a long time, he did not flaunt it, but he had no issues with people knowing he was gay. As I had always been in the closet, it was a big change for me, but a change that really became me. I loved being gay, I loved having a boyfriend and loved living gay with him, loved having people know we were a gay couple. I was not over the top effeminate in public but just did what came naturally in androgynous clothing, pierced ears, jewelry, even sometimes putting on subtle makeup with eyeshadow, rouge, light lip gloss. I got my nipples pierced.

There was no doubt who was the feminine one in the relationship. Dave's sister Jen would come over and I'd be shy and demure, holding hands with Dave. One big life event was meeting his mom. We had been living together for not even six months when Dave told me it was time to meet his mom. In terms of relationship dynamics, meeting someone's mother means things are serious in a relationship. It was heaven meeting his mom, she was so nice to us, and it really cemented the bond between Dave and me.

Another big event was going to the Gay Pride Parade with Dave. It was intoxicating for me for many reasons, but one reason was Deb. I had called her one day out of the blue and unlike every other time since the last time we broke up, she answered the phone. She seemed very happy to hear from me, thrilled to hear from me. Then I got up the nerve to tell her I was gay, when she told me "Yes, I know, I've always known you'd be gay." We had a long talk and she said she was so proud of me for coming out. I tingled inside telling her this, it was one of the most exciting feelings ever, telling an ex-girlfriend that I was gay. She was the first person I ever came out to. It was one of those things that even though I was always madly in love with her, for some reason it never seemed to work, our relationship.

Maybe I should tell you about me and Deb. She was a hottie, skinny blond, with tiny breasts and while she did not wear a lot of makeup, she always did her eyes dark with long lashes. Deb came off as a heavy metal chick and always turned heads whenever we went out. Our relationship was strange, she always kept me at arm's length, always in the dark. Screwing her was heaven but it took an act of congress to get her clothes off and into bed. She was barmaid at a restaurant and how I ever scored with her is still a mystery, but I was persistent and eventually got lucky with her. Sex with her was divine, but again I had to work for it. She lived with her dad, and he worked at an auto dealership, so I'd go over to her place in the afternoons.

I'd go over wanting to get laid and she'd make me watch her iron her work blouses and such, often just wearing a long shirt and panties, talking to me about mindless stuff the whole time. Sometimes she'd give it up, other times just tease me all afternoon then send me along with no pussy. When I did get lucky, it was fucking insane good sex. Somewhere along the line she subtly emasculated me. All these mind games and holding me at arm's length for sex, and some of her psycho bitch hissy fits left my head spinning. In the middle of all this she talked hypothetically about us being married and what that would be like. I'd had never even broached the subject with her. But the sex. Her blond hair, slender lithe body with small breasts, lovely legs, perfect little ass, tasty tight pussy was the best I had ever had. Even though I know I'm gay now, she was the hottest and I had fucked quite a number of hotties in my life. It was fucking the best sex I ever had in my life despite all the hurdles, hoops and mind games I had to jump through.

There was more to the emasculation than the verbal and non-verbal withholding of sex. Deb would bring cotton thongs to bed when we did get in bed for sex. These were men's thongs, but very thin cotton thongs in bright colors; cyan teal, bright yellow, bright red. If my roommate would have seen me in one, he would have thought they were panties. Needless to say, they made my dick very hard, they felt like panties on me. Deb loved feeling my penis through the thongs, it made me so hard and made us fuck like rabid dogs. She'd finger my asshole as we fucked to make me go spastic inside her for incredible ejaculations. Deb gave my penis a pet name, "Slippy", and she'd say how pretty 'he' looked as she rubbed 'him' through the bright colored, thin cotton thongs.

Could she tell something about me that I never told her? That once when I was married and my wife was out of town, I put on a pair of my wife's panties under my jeans and went to a gay bar and picked up a guy? Or when I lived in a house with a girl roommate and a guy roommate, I would sneak into the girl's room when she was not around and sneak a pair of that girl's lovely panties to masturbate in?

Deb was such a hottie she could do as she pleased with any man. Deb saw something in me, of what was there in my psychological make up. She knew by subtly emasculating me with touches of femininization she would know if I really was man enough for her. I wasn't. We broke up three times. Each time I felt less sure of myself around women. I was a handsome, boyish guy. I had scored with Deb, most guys never got to first base with her. I was so confused and lovesick; it just was not a normal, rational relationship.

After the last breakup I had sunk into compulsive masturbation. My straight roommate was a slacker, a jerk. He had literally hundreds of Playboys and Penthouse magazines in his room, piled high, all over the place, spilling out his closet also. We were good friends, so it was never a problem that I could borrow any magazine at any time. It was unspoken, I never 'borrowed' them when he was around, but he knew. There was a lot of masturbation going on with both me and my roommate, though we never, ever, masturbated in each other's presence. I masturbated a lot in the time after Deb before meeting Dave. In some of the Penthouse magazines there were letters from readers about sexual exploits, occasionally there would be a letter about guy-on-guy sex. Those letters would turn me on the most and I learned by the magazine cover, which ones had the guy-on-guy sex letters, they were always my favorite to read and masturbate to.

After the last breakup with Deb, I gave into my longings and started calling the gay chat lines. I'd had sex with guys before Deb, but now after the last breakup, having sex with guys was all I could do. I was a flop with women, no connection at all, no ability to sway them, they had no interest in me, it was almost like they knew. Most of the anonymous gay encounters I had were shabby and unfulfilling. Sometimes my roommate would spend the night at his girlfriend's place, and I'd bring a guy over or I'd go out and hook up with a guy. In the time after Deb before I met Dave, there were dozens upon dozens of encounters that I had with other guys, mostly unfulfilling. Then I met Dave, and it really was magic.

So, getting back to Deb, I invited her to the Pride Parade with me and Dave and she said she wanted to go with us. Other girls who were gay or bi would surely have lesbian feelings towards Deb, but she had none, she thought lesbians were weird. But she thought guys being gay together was amusing. Dave and I as a couple would talk about our incredible first night together. In inviting Deb to the gay pride parade with us, I told Dave it was Deb who called that first night we hooked up. I was unsure if I should tell Deb about the night of her call. She seemed more interested in me now that I came out as gay to her, not in a sexual way, but fascinated by it, almost like the stereotypical girl with a gay guy friend. It was fabulous meeting her there at the gay pride parade, I really did not think she'd show up. Honestly, it was a little awkward being there with her seeing me and Dave hold hands and kiss in public.

Just having her there with us made my sensation of gayness soar. There was a little guilt and shame inside me, not shame that I came out as gay. It was a shame that she was so hot, with me having been so madly in love with her for so long and I was no longer her boyfriend. Shame that I was not man enough to be her boyfriend anymore but femme enough to be the boyfriend of a hot guy like Dave. In some ways it validated me coming out, being there with Dave in the acknowledgement that we were a gay couple, like there was no turning back now, especially with Deb seeing it with her own eyes. Whatever uncertainty and shame swirling inside me was more than counteracted by the exhilaration I felt holding hands with Dave in public, that tingly feeling showing the world you are gay.

Deb always looked hot, being there with us at the pride parade was no exception. She wore frayed denim shorts and a pink bandeau stretch bikini top under a white blouse unbuttoned enough to see a little of her pink bikini top. It made me wonder if she wore the bright pink bandeau top because of me telling her I was gay. I wore loose jeans and sandals with a loose fitting bright yellow tank top, it was actually an oversized girls' tank top and it was easy to see my bare, hairless chest. It felt rather stimulating that it showed off my pierced nipples. Maybe it was a little too gay to have done this, but I painted my toes pink, wanting the world to see how gay I really was.

Again, not knowing if Deb was going to show up with her to see my toes, there was no turning back now. Dave wore shorts and a tee shirt and just looked like regular guy, a regular guy holding hands with his femme faggy boyfriend, much to Deb's amusement. The parade was fun, and Deb squealed in delight many times seeing so many different gay tropes. Her favorite were the drag queens. One 'girl' in particular was stunning, not like the over-the-top flaming drag queens but just a very pretty boy in a dress, that really, if you didn't know better, you'd have no idea the 'she' was indeed a 'he'. Deb whispered, "you should be like her" and gave my hand a squeeze.

After the parade the three of us went out to a late lunch. I must say it was quite different being out with my boyfriend having lunch with my ex-girlfriend. I had gone to the restroom and when I got back Dave and Deb were in an animated conversation laughing and having fun. Jokingly, I asked:

"Talking about me?"

"Of course, we are silly," Deb replied. "You're so cute and so fun to tease. Who knows what we've been talking about."

Deb got up to use the restroom. Dave gave me a quick kiss and patted my leg as I sat back down, and he whispered "you're a doll. I love you so much. She is a hottie and I am impressed. You are so much better off with me. She's nothing but trouble, she's a doozy."

I always thought she was borderline crazy, but she was such a hottie and I always had wanted her so bad that I fooled myself that it would work. Just like I fooled myself I was straight, so when after meeting and moving in with Dave I was never happier sexually or emotionally. Getting back to Deb, and I hate bringing her up so much, but I really think it needs to be said about her being somewhat whack and how that ties in with me accepting that I am gay.

Anyway, in between the second and third breakup, Deb and I were at my house at the time and the roommate girl (who I had snuck her panties) and the other guy had both moved out, so I had the place to myself. Deb and I had been drinking and we had been apart easily six months before getting back together this time. She asked and I should have lied, but she pried me and like an idiot I told her I had been with other girls during the breakup. She went into a rage and was uncontrollable as we argued. It was really insane and out of frustration I picked her up, she was kicking and screaming, surprised the neighbors didn't call the cops. So, I carried her out the screen door in front and set her in the yard to let her cool down. I just sat her there and headed back to the house.

Turning around, I looked at her and she was in a fetal position not making any sound. Going back to check on her I knelt to see if she was okay when she flew up at me and bit me on the arm. This was no 'love nibble'. She bit into my arm as hard as she could and would not let go, it was fucking insane. I would never hurt or hit her, so it took forever to get her to release my arm from her bite. Finally, she did, and I had teeth marks in my arm for over a week. Well, with all the "you fucking bastard's" and "how could you's" thrown at me plus the bite, this second union did not last very long.