I had a Domme many years ago with whom I shared a rather unique relationship. We met on a BDSM chat site, and began our relationship by exchanging filthy fantasies. She was going through a tough time in life, and used our fantasy role play as an escape. She was recently separated from an unhappy marriage that had ground her down emotionally, and resulted in her becoming quite overweight. They split after her husband left her for a younger, fitter woman. She worked a dead-end job that didn't value her intellect. Her weight, low self-esteem, and long list of fetishes left her feeling confined to online relationships, and that no man would want her in real life. Her imagination was stunningly perverse, and she was quite articulate, and her mind made her appearance irrelevant to me. We would one-handed type to each other long into the night about our deepest, unrealized fantasies. Our online exchange slowly turned to talk of real life adventures.
The expectations were brutally honest. She needed an outlet to her frustrations. She wanted a plaything to use and abuse, to boost her ego. She wanted to feel powerful in one aspect of her life. I wanted to be pushed out of my comfort zone, and forced to explore my bisexuality. I wanted to be used without climax, and sent home to jerk off and think about what I'd done.
Our first "date" was fiery. I'll write about it another time, but believe me when I tell you that she ravaged me. Repeatedly. For 8 hours. I was the first man she'd had since she married, years ago, and my young, fit body was hers to do as she pleased, with regard only to her own pleasure. My orgasms were banned, and my cock was not welcome inside her.
We had regular sessions in the same vein, and her confidence grew. She took other partners - vanilla mostly - to fuck her like I wasn't allowed to. Above all, she became obsessed with watching me suck cock.
The road to oral fixation started one night when I came over, she had me go down on her in her living room while she finished the TV program she was watching. She was unusually wet that day, and after coaching me to get my tongue deep inside her, and slurp up all her juices, she told me that her ex husband had just left before I got there, and I was sucking his cum out of her pussy. She was pleasantly surprised when I didn't miss a beat, and pleased that my creampie fantasy wasn't just horny online fantasies.
She took it as her personal mission to teach me to suck cock. Cream pies became the usual start to our night. Sometimes she would leave me trussed up on the bed to go fuck one of her other guys. Other times she would make me lick her clit while another man fucked her. Eventually, the inevitable happened. Her favourite partner -a mid-40s, fit businessman - pulled out of her pussy, and thrust into my mouth. I didn't fight. I tried my best to suck him at that awkward angle. The feeling of his hardness in my mouth is something I'll never forget. Eventually he stopped, and finished up inside her. I was told to clean her up, and then clean him up, which was another first. I did what I was told, and as I had his deflating cock in my mouth, he said to her
"That was possibly the worst blowjob I've ever gotten."
She apologized, and promised him that it would be better... far better, and soon. I was sent home without further ado.
When I got home, I found an email from her telling me it's time for me to learn to suck cock, or the relationship was over. So I created a profile on a gay cruising website called Squirt looking for chat, and to find good tips on sucking cock. (Username Str8Boy4Chat, if you're interested ;) ) I also was seeing if I could work up the guts to actually do it...
We would have "training sessions" where I would go over to her place, and she would have me give her head on her dildo for hours. She gave me a huge dildo of my own to practice on at home. I sucked a few different Squirt members' cocks for practice, and shared the experiences with her through my profile. When I felt that I was sufficiently good (judging by the explosive cumshots in my mouth, I was doing something right), I emailed her to let her know. She wrote back a couple of days later, and said "We will see about that... come over late night Tuesday." I spent the next couple of days in nervous anticipation, trying to figure out what she had in store for me.
Sure enough, on the day of, I found an email from her. "On your way stop by the Pioneer gas station just off the highway. Wear your blue jacket. Go inside, and ask the attendant for the washroom key. Go to the washroom, get on your knees, and when he comes in, suck his cock, and suck it well." My mind started going a mile a minute, my heart in my throat. I considered bailing, but forced myself to get in the car. I thought I would explode as I pulled into the gas station. My hands were shaking, so I jammed them in my pockets. I went in, avoiding eye contact with the clerk, and asked for the washroom key. It was already sitting on the counter. I grabbed it and shuffled outside, found the male washroom, and let myself in. I left the light off, turned, and knelt in the dark. The room stank like old piss. I was glad the lights were off. I heard footsteps outside, the doorknob turn, and the blast of cold fall air hit me.
He flicked the lights on, and laughed at me kneeling there. He was tall - probably over 6 feet, and solidly built. His crotch was right at face level, and the full weight of what I was about to do hit me. I started to tremble in nervous anticipation.
"Strip, cocksucker." He said firmly.
I hesitated, and then slowly stood up.
"Too fucking slow!" He grabbed me, turned me around, pulled my shirt and jacket up over my head, and then ripped my pants and underwear down. With my pants around my ankles I was barely prepared for him slapping my ass hard with both hands. I stumbled a little, and fell against the wall. He didn't give me any space, pushing me down to a sitting position, and then unzipping his pants.
His cock was semi-hard, and already bigger than mine was fully erect. He held my head with one hand, and slapped me in the face with his cock with the other.
"Open up, whore... show me what you're good for" He grunted as he put the head on my lips.
I stuck my tongue out, and flicked it over the uncut head, wiggling the tip between the foreskin. He moaned softly.
Encouraged, I closed my lips around the head, and lapped at his foreskin softly. It was like the blood flowed in a sudden burst to his cock, and it swelled at my slightest touch. My hands found the base of his cock, and cupped his balls gently as I slid down until his cock hit the back of my throat, then started to pull back off slowly. I cinched my lips down over his cock, and milked it all the way back up. I slid back down, this time a little farther, and made myself gag a little. His cock was fully hard now. A solid 8 thick inches. I wrapped my fingers around just below my lips, and then slid back up his cock and inspected. Putting it all the way in my mouth was only halfway.
Fuck.
I tried again, this time making a swallowing motion with my throat, and fighting the gag reflex for all I had. Strangely, my whole body reacted. I got tingly, and my cock twitched, and started to harden in my pants.
Whatever this feeling was, I wanted more.
