Ultimate Humiliation (part 7)
I was on top of the world when my wife caught me in an affair and my life became one humiliation after another. I hope you enjoy this work of fiction.
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Brad picked me up to take me to dinner. Now, as Jennifer, I would be Brad's dinner date, after which he would take me to a club where Tgirls go to meet men. I wasn't particularly looking forward to that because I feared seeing men that I knew.
Just the same, I did look forward to being on a date with Brad. I knew that he liked me as a girl, but I knew he didn't want Mary to know. While Brad was a party to my ongoing humiliation, he was nice to me, so I would pretend to Mary that I was simply submitting, but not enjoying.
Brad walked me to the car and got my door for me – he knew how to be a gentleman! He told me that I looked really pretty, and I hoped he was right – not just buttering me up. I slid next to Brad and put my hand on his leg, moving my hand to his crotch. I could feel that he already aroused, and knew he would need draining, and I wondered how he would have me do it.
Brad was a perfect gentlemen as he escorted me into the restaurant and with my chair. "Does my voice sound femme enough?" I asked.
"It will get you by tonight," Brad replied, but I'm sure it will get better with practice. Would you prefer that I order for you?"
"Thank you," I replied, "but I'd like to see how I do." I was beginning to believe that Brad's kindness was driven by more than just his hard cock.
"I like being with you, Brad," I said.
"I like being with you," he returned, "but Mary must not know."
"I understand," I responded, "I will make sure that Mary thinks that you are just humiliating me, but I hope we can enjoy our time together."
We had a nice dinner and I couldn't help but realize what dangerous territory I was in. Having an affair with a woman is what got me into the mess I was in, and now I was having an affair with Brad. Mary would be really pissed if she ever found out, so I needed to be sure she never did!
After dinner Brad walked me to the car. It was getting dark and the parking lot was not well lit. When we got to the car, Brad asked, "Would you please take off your panties?"
He asked me – that was wonderful – I knew that I really didn't have a choice, but he was being so nice about it. I removed my panties and handed them to Brad, and he stuffed them into his pants pocket.
Brad kissed me and slipped his hand under my skirt. I kind of liked it, and when he felt the tape that was holding my cock in place he asked me to remove it.
"But what if Mary checks me and finds it gone?" I asked.
"You can put it back on afterward," Brad replied, "if Mary says anything you can tell them that you can tell her that you had to pee."
He said "pee" and not "piss" – even now he was being gentlemanly.
I pulled off the tape, glad I had been shaved, and handed the tape to Brad. He stuck the end to the rearview mirror so I could use it again.
Then Brad did something completely unexpected. He knelt down, lifted my skirt and began to suck me. Brad, of all people was sucking me. I had no idea he would do such a thing. I was breathing harder and soon I came in Brad's mouth – it felt so wonderful!!!
Brad swallowed and stood up, leaning over to kiss me. "Do you want me to rinse my mouth out first?" he asked.
I pulled him to me and kissed him, reaching my tongue into his mouth, tasting the cum he had just milked from me.
"Mary must never know," Brad said, "she would kill me!"
"She'll never know from me," I said, "but I'm so surprised about this."
"Jennifer, dear," Brad said, "you may not understand this, but a girl like you brings out something in a man that is normally well hidden."
I replaced the tape holding my now-soft cock in place and Brad opened my car door, letting me in. I hoped that I could bring out more of his hidden surprises.
Brad drove me to the club and walked me to the door and inside. Mary was there and Brad took me to her.
"Pick Jennifer up at 11pm and feel free to have your way with her then," said Mary.
Brad departed and I was now under Mary's supervision.
"How was your dinner with Brad?" asked Mary.
"Dinner was fine," I responded, "but I was so humiliated as he paraded me around for everyone to see!"
My attempts to protect Brad proved effective when Mary said, "Good, then Brad is doing his job – I think I'll have him spend more time with you."
I liked the sound of that, but put on a pouty look to not give it away.
"Careful," cautioned Mary, "or I might just put Brad in charge of you!"
"What do you expect of me tonight?" I asked.
"I want you to mingle here, and meet men, and be nice to them – VERY NICE! – You know how to please a man, so make sure you do."
I felt really uneasy, but fortunately men came up to me and asked me to dance or to buy me a drink. I danced with some of them and felt their hardness against me. When they asked if I would blow them I quickly agreed, and we went out to the parking lot. The lot was not lit, so there was good cover from the darkness. I saw that several other girls were sucking their guys.
As soon as the guy came, I swallowed and he thanked me, walking away. These guys were certainly not gentlemen, and made me appreciate Brad even more.
The guys who bought me drinks talked with me, but they really didn't know what to say, so I usually helped get to the point by asking, "Is there anything I can do for you?"
At this point some would ask for a blowjob, while others couldn't seem to find the words, so I had to offer.
I preferred giving blowjobs to getting fucked, because they are fast and not at all messy.
By the end of the evening I had given nearly a dozen blowjobs, probably all that I can safely swallow. Mary had been watching me most of the night.
Mary approached and said, "You've done a nice job in pleasing the men – how did you like it?"
I did like it a little, but couldn't show it. I replied, "I'm just doing what you told me to do – I recognized about half of the guys – I just hope they didn't know who I am."
"They do now!" said Mary, "I made a point of telling every one of them!"
Mary was a master of humiliation, and I saw no end to this. An occasional good time with Brad was the best I could hope for.
Brad came in at 11 as ordered and led me away. Once outside, he tried to kiss me but I stopped him, saying, "Please don't – I've been giving blowjobs all night."
He pressed his lips to mine parted them with his tongue. I wished I could just run away somewhere with Brad, but I knew that would never happen.
Brad ran his hands over my buns and I instinctively spread my feet apart. He lifted my skirt to my waist and slipped a finger between my cheeks. I would have to remember to get my panties back from Brad before we get home.
"You're dry," Brad said, "I'll hurt you if I try without lube."
"I have some in my purse," I said, handing him some.
Brad was wonderfully gentle as he applied lube and worked his fingers in and out of me, preparing me for his cock. Soon he was pressing into me and I welcomed his entry. He gave me a good fucking and wrapped his arms around me as remained in me after he came.
"Oh Brad," I said, "you are so wonderful! I just wish I could always be with you."
"Let's just take it one day at a time," he responed.
He pulled out and used a wet wipe to clean up. I knew that some guys made girls like me clean them up in their mouths, and I was grateful to Brad for his courtesy to me.
Brad drove me home, and Mary was waiting for me.
"This is just the beginning," she said, "You will be spending the rest of your life as a woman."
As I lay in bed that night I feared what lay ahead, but did enjoy my time as a girl.
–––––––––––––––––––– To be continued ...
Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)
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