Friday, January 18, 2008

Deeper Needs

Terri was always understanding and supportive of my desires to wear lingerie. Every morning as we dressed for work, we’d put on our pantyhose together. We’d wear each other’s things. There was one shared panty drawer. She was fine with me wearing lingerie while we had sex. We engaged in many fantasies involving me putting on women’s underwear.

An example was her as the clerk in a lingerie store helping me try on bras and panties in the fitting room. At first, she's a bit put off by having a man trying on the delicates, but she's trying to be professional. The fit of the panties wasn’t quite right, and she dutifully fellated me to get my erection to go down. All in the interest of a proper fit, you understand.

Still my need for humiliation involved fantasies such as getting caught trying on panties and being punished for the act by being forced to put on a bra and pantyhose and heels; then being butt-plugged and made to suck a dildo while being verbally degraded. It’s that whole shame thing. Terri was a good actress, but she was never going to be a dominatrix, even a soft one.

At the same time, her needs weren’t being met by a sissy who was a lousy fuck. Most of us are, after all. Let’s face it: while real men are focusing on the feel of pussy and making a woman feel good, we’re busy fantasizing about bras and panties and hose (oh my!). We can’t get it up if we’re not fantasizing or engaging in sissy behavior. That’s the plight of sissies.

So over time, she started to look elsewhere for real sex, and as I look back, I can’t blame her. She would be out late with some lame excuse while I was home dressing up and jacking off.

We had discussed the possibility of a three-way, and she was open to the possibility. I had confessed to her that I wanted to suck cock, and that didn’t bother her. I hadn’t told her that I had done it once before we met. What a wonderful memory that was.

In a crazy moment five years earlier, I picked up two women in a bar. I knew one of them was a very passable transvestite. I was pretty drunk. I invited them to my apartment, and we started having some fun. The TV was just beautiful with long, slender, pantyhose covered legs.

I showed them that I was wearing pantyhose and a bra. The TV and I started feeling each other up. The woman sat on the bed while I knelt in front of the TV. I felt up her legs and pantyhose and started to rub her crotch.

The woman said, "I think he wants what you have up there." She pulled down her pantyhose and panties and revealed a beautiful 8" cock. Now this was a dick any woman would enjoy pleasuring. I was delighted to hold it and stroke it, and in short order, I put it in my mouth. It was wonderful feeling it slide in and out of my mouth while hearing his feminine voice moan. Before long, I was sucking cock like a whore, my head bobbing up and down while I kept a good grip on the shaft stroking it. I was making shameless slurping noises. What a sissy cocksucker!! He didn't cum, but I wanted him to. I felt wonderfully feminine and submissive doing this as the woman looked on. She didn't really humiliate me, but she was encouraging and saying things like, "That's right, suck that big cock!"

I never sucked another real one, but ever since then I've enjoyed the sensation of my lips wrapped around a dildo and my tongue licking its head especially at the command of a dominant woman. Of course, it's also a lot safer than the real thing. There's just something absolutely overpowering about a woman holding a huge dildo between her legs ordering me to suck her cock for her amusement.

I can understand how women can sometimes achieve orgasm from giving head. At times I’ve worked myself into such a frenzy that I’ve gotten lost into a pseudo-orgasm of my own. Eating cum is particularly emasculating. It’s something I often find difficult to do on my own unless a woman is ordering to do it. Girls laughing at me while I'm licking it up makes it especially humiliating and erotic.

Oh... I’ve digressed, haven’t I? Like I said, Terri never knew about my cocksucking experience, and we never had that three-way. I couldn’t handle the fact that she was sleeping with another guy.

Today, I have cuckold fantasies. I wonder now what it would have been like if I could have stayed on as her sissy maid. Maybe she could have talked her lover into letting me suck his cock while she looked on. Then they could have ordered me into the corner to sit quietly while he fucked her good, they way she really needed it. He could show me how it's done. Then while I’d sit there in jaw-dropped awe while she screamed in ecstasy, at least I’d have the pleasure of knowing that the dick that was giving her such a noisy orgasm, I got hard for her with my own sissy mouth.

So Terri and I split up. It was mostly amicable, although we argued over some clothes. “No, those were my panties!”

Only a sissy boy would argue over a pair of panties.


Anonymous said...

So why didn't he cum? Was he too drunk? Were you? Did you just need more practice? How did you feel being unable to satisfy him? You talk about what SHE said, what did the TV say? Did he ultimately get off? Did you? Did she? How?

Janine the Sissy said...

Fantastic blog, really got me going. I just love hearing about sissy humiliation. I do love to be told what to wear and how to act, by men, TV's or ladies.
Keep up the good work,

Little Pantyboy said...

Jamielin, I'm not sure why he didn't cum. He might have been too drunk or maybe I wasn't persistent enough. Like I said, I was pretty drunk. He didn't really have much to say but moan while I sucked and licked. He was evidently liking what I was doing, but was remaining pretty passive the whole time.

Nobody ultimately got off. I got off alone after they left sometime later. I do wish he had cum for me. That cock was so beautiful.

The TV and I talked a little because I was so fascinated with how good she looked. Her legs in particular were so long and silky. Her trick was to wear two pairs of pantyhose. I didn't come on to the woman at all.

They were both a bit mysterious. If I had to guess, I'd say they were just a couple who got off with him being out in drag and her watching him with other men. This scene was probably a switch for them because he probably did the sucking in most of these situations. Although, it must have been quite a sight watching her boyfriend/husband in drag with another guy sucking his cock.

Janine, I too love to have women calling the shots, telling me what to do. I've been in a number of sessions with dominatrixes, and it's such a turn-on for me.

Thanks for your comments!

vicki said...

when me and my mistress split up we argued over panties, she introduced me to permanant pantie wearing and we shared the same pantie draw. there were a few pairs that were designated mistress only panties that i was forbiden to wear, and a few that were sissy panties that she ordered me to wear at times. she had a bit of a pantie fetish too so when we split we had over 170 pairs of panties, there were a few heated dissucsions over who got what pair lol. still today 10 years after our split i still wear panties 24/7 and do not own any male undies, so id like to thank her for that x