This story is about a woman humiliating a man. It includes crossdressing and cuckolding.
After a heartbreaking divorce I wasted a a few years in mourning, reflecting on all the things that had gone wrong in the relationship. What had started as an equal-sided affair turned into a female dominated one. Basically, her pussy ruled.
Finally pulling myself out of a sea of self-pity I began dating again, meeting a nice lady. Kathy is a tall woman, very nice boobs, with a pretty smile and clear skin. Usually, my eyes gravitate toward the ass, but with Kathy, it was her face, her chest and her legs.
To my surprise, we seemed to hit it off. Maybe this time, I thought, I had found true love. The only concern I had was keeping the grim aspects of the past hidden.
But as we continued seeing each other, the fear that the past would rear its ugly head and reveal my true character haunted me. Flaws in my personality have contributed to my downfall in maintaining a relationship and I was afraid my real self would show itself once again and ruin everything.
What was I worried about? Well, there a few things. The first is I have an almost uncontrollable oral fixation to the extent my mouth and tongue become the primary sexual organs. When I'm in bed I can't seem to stop licking, sucking and tongueing.
The second problem is my need to get frilly. Despite being too big and too manly I am unable to resist dressing up in sexy female garments. I can't keep my hands and body off of scanty panties, nylons, mini-skirts, corsets, and any kind of lingerie. Satins, silks, and soft material send chills of excitement through me every time I put them on. Make-up and high heels add to the sensation and my craving to crossdress takes over. Obviously, I have to work hard to try to keep this perversion hidden from my girlfriends.
The third problem involves a particular embarrassing personal deficiency. Down south, my male appendage is a bit on the small size, ok, more than a bit, and to add insult to injury, the little guy tends to shoot off fairly quickly whenever he gets excites which is quite often.
So far, every woman I've been with has eventually tired of my pathetic attempts and found the need to enjoy larger, more satisfying equipment, usually while we're still going together.
And finally, I seem to gravitate into a submissive role with my lovers. And if that's not bad enough, while submitting to my girlfriends, I have this insatiable need to be debased, humiliated, enslaved and cuckolded, traits for some reason are not generally appreciated by many women.
Not surprisingly, these depraved qualities seem to lead invariably to one inevitable conclusion. I always lose the girl, sometimes helping her out finding a better substitute.
The first fetish, loving oral sex isn't a much of problem with women, in fact, this particular obsession of mine is the main reason, other than money, women stay with me in the first place. Lots of women are used to the guy jumping on them, pounding away, and rolling over and going to sleep.
Not me. I spent hours finding artful ways to please the woman with my mouth, my tongue and my fingers. Oral orgasms are my speciality, especially when I don't require reciprocation.
It's the other three kinks that always cause the difficulties with the gentler sex.
When you're slightly different than other men it's difficult to find someone who understands, especially a man's need to dress like a woman. Whenever I'm finally caught it has led to disastrous results, usually a lot of screaming then one of us moving out.
And, needless to say, trying to explain to a woman that you get off on being humiliated is a tricky undertaking. Most women don't understand it. They find the thought of a man desiring humiliation disgusting. Usually just the confession leads to a brutal and final breakup with my sense of pride flushed down the toilet. Some would say that that resul is exactly what I crave. They may be right.
The story of how I got this way is told in other tales. My wife, or I should say, my ex-wife led me down this path of depravity, but I have to admit I was more than a willing victim. Now, after a messy divorce, I vowed to leave all my quirks behind.
It didn't work out that way.
The first girlfriend after my divorce, Kathy, learned quickly how easy it was to get me to return to my old habits.
The first step was easy. As I was a sucker for oral sex all of my relationships soon got sort of one-sided. When the lady realized I loved going down on her and would gladly do it over and over, and when she got tired, she discovered I didn't expect her to reciprocate she became comfortable with getting hers without worrying about mine.
Kathy and I dated for a few weeks and everything went along in the usual way, kissing, hugging, and a grope or two. After a few expensive nights at the finest restaurants, she said we could go all the way.
Back home, I slowly stripped her of unneccessary garments then spent an hour or so licking, sucking, and teasing every part of her smooth and delicious body. After three orgasms and finally sated, she allowed me to mount and ride until I climaxed. The first time I managed to last a good half-a-minute, a record for me.
The combination of oral skills and fancy dates had an effect. Kathy enjoyed my tongue and she liked the money I spent on her, so she allowed us to become a couple. Sure we fucked but not before I spent a lot of time between her legs, pleasuring her with many lickings and multiple orgasms. I was proud of the way I made her cum from my oral abilities.
Every night it was the same. My head betwen her thighs until she had her fill of mutiple orgasms, then, when it came to my turn she would just lay there on her back, almost bored. To her credit, she seemed to tolerate my quick, short thrustings. Her casual, unresponsiveness to my penetration was a far cry from the passionate groans my tongue evoked. The fact she didn't seem to get excited by my love-making only added fuel to my masochistic side. Recognizing she was not pleasured by my penetration caused me to get more excited and cum quicker.
Knowing she preferred my mouth to my cock didn't bother me. Frankly, I was used to it and it had been so long since I had been allowed to fuck someone I was grateful she allowed me to penetrate her hot body.
Things were going smoothly until one weekend on vacation. Arriving in a small, out-of-the-way town on the ocean, she discovered she had forgotten to bring our stash of contraceptives. This was a problem because she would not let me near her precious pussy with an unclad penis. She was not willing to take a chance on getting pregnant.
"Damn it," she said as she snuck under the covers.
"What is it?"
"I left the box of condoms at home."
I got a glimpse of her naked form just before she disappeared beneath the sheet. Seeing her sexy body had already caused the little guy to awaken and proudly strut his four inches.
"I could go get some." I didn't want to beg, but I was getting close.
"No, it's too late now, nothing will be open."
Scooting next to her, I reached out and caressed her thigh. Her skin felt soft and smooth. My tongue ran across my lips.
"Even though we can't do it," she said, "you can have your fun if you want."
It was interesting how licking her had become my fun. She was the one getting the pleasure, but we had both gotten accustomed to her pleasure being mine that it was easy to go along with her reasoning.
My hand covered one of her rather ample breasts and I squeezed gently. Her nipple sprang to attention as I played with it and she leaned back on the pillow with her eyes closed.
My lips circled her other nipple and bit softly. She moaned. My tongue circled around the breast, my teeth nipping gently and my tongue flicking.
After a full five minutes on each breast I worked my way south, pausing to tickle her belly button with my probing tongue.
As I ventured farther, I felt the sheet cover my head as she settled in. I was her toy, being used for her satisfaction. There was a calmness that settled over my mind and I felt that this was where I belonged.
My head rested between her thighs and I explored the area where the legs met, licking the sweat that settled there. My tongue snaked up and toyed with her clit, rousing it then slipping away to lick other spots. Once in a while my tongue slipped inside to taste her juices, then I would tease her clit once again. The art of teasing became my goal.
Using all the skill I had, I slowly caressed, tactfully licked, and gently sucked her clit. Pausing as I felt her orgasm near, I moved down and with all the adoration I could muster, I mouthed her pussy before penetrating it with my long tongue as far as I could reach. Her juices coated my appreciative appendage.
Finally, unable to withstand my oral attacks any longer, Kathy arched her back and yanked my head deep into her cavern.
She came fiercely, yanking on my hair as she did. The pain only added to my pleasure.
As she floated down from her climax I remained glued to her pussy, licking gently on her little button. This was a special treat to me as I always enjoyed the aftermath of her intense climax, soothing her with gentle caresses of my tongue.
Scooting up alongside her I held her tenderly, cuddling with her body against mine. My little guy pressed against her thigh, anxious for a little attention.
For a moment, I entertained the thought she might return the favor and go down on me, giving me some release in a way I have never experienced. Kathy, as well as many other girlfriends, had never given me a blowjob. My little fellow thought this might be a good time to start.
Kissing her shoulder, I stroked her breast, teasing the nipple by rubbing it between my fingertips. My hand left her breast and traveled south. Kathy is especially sensitive on the inner side of her thighs so I zeroed there with my fondling.
It seemed to be working as she moaned in response to my caresses. While I was forming the words to ask her to return the favor she reached out and grabbed my head, pushing it down. She didn't stop shoving until I was back at the shrine.
Oh well, I thought, maybe if I please her again she will return the favor.
