Moments of Weakness (part 5)
This story was inspired by a hot picture that became the setting for the temptation scene in part 1. Little did I know that a moment's weakness would change my life! I hope you enjoy this work of fiction.
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The next day I went to work, thinking about how strange is was to buy the bra and panties last night, and how much I liked the help that Helen had provided. I deciced to call her and ask about shaving those "hard to reach" places.
I called her and said, "Hello Helen, I really appreciate your help last night."
"I was glad to help," Helen said, "I like working with boys like you."
"Last night I shaved my body," I said, "but there were some places I couldn't reach."
"I don't have to work tonight," Helen replied, "if you can come to my place at 6pm I'll take care of that for you."
I thanked her and took down her address.
Throughout the rest of the day I wondered what would be happening tonight. In her home, much more could happen than in the Walmart changing room – I didn't know what to expect but planned to enjoy every moment of it.
The day went by quickly, and soon I was driving to Helen's. I had the bra, panties and other items in my car.
I arrived at Helens and she welcomed me in. She told me to undress and come back in the bra and panties.
I tucked as Helen had taught me – each time it was getting a little easier. I put on the panties and the bra, and stood in front of the mirror for a bit, and then went to Helen.
Helen smiled and said I looked good "en femme". She placed her hand on my crotch and said I was nice and smooth, just like a girl. She showed me how to put on lipstick, and had me practice until I got it right.
"I didn't ask you why you were dressing," Helen said, "it's none of my business, but if you don't mind, I'd like to know."
"I'm going to be blowing men, and I know some men like their cocksucker's to be fem."
"Yes, they call them sissies," she said, "Do you like sucking cocks?"
"Yes, I really do, and want to be the best cocksucker I can be," I responded.
"That is commendable," said Helen, "so you are going to be dressing only to please the men you blow, not for your own enjoyment?"
"That's correct," I said, "if not for cocksucking I wouldn't dress as a girl at all."
"Thanks for sharing that with me," Helen said, "now I can help you better."
She walked around me and pointed to the small thin patch of hair at the bottom of my back, "is this the only place you couldn't reach?" she asked.
"I think so," I answered, "but do let me know if you see any other places."
Helen led me to the bedroom and brought in a small tub of soapy warm water, a razor and a washcloth. "Now take the panties off and kneel on the bed, on all fours."
I did as instructed and Helen quickly shaved the hair from the bottom of my back.
She spread my cheeks and asked, "what about this?"
"I didn't think that would matter," I said.
"Well, it's up to you, but if you are going to be servicing men as a sissy, some may want to fuck you, and a hairy crack is not very lady-like."
"I hadn't thought of that," I said, "please shave me there as well."
Helen did and said, "nice and smooth – and very inviting."
"Really?" I asked.
"Any man who likes to fuck a girl in the ass would find yours very inviting," she said.
"I've never had that before," I said, "I'm not sure I will like it."
"Either you will learn to like it or you will learn to fake it if you want to serve your man well," Helen explained, "I can give you some practice if you like."
"I have trusted you in everything so far," I said, "so I'll continue to do so."
"Just stay there like that," said Helen, while she left the room.
Upon her return I felt Helen rub something wet on my hole – perhaps lotion or lube of some sort. Then she took hold of my cock and stroked me to erection, and placed something to my hole.
"This is a small dildo," Helen said, "you will take this easily."
She pushed it into me – it felt a bit strange, but Helen stroked it in and out of me while squeezing my cock, and it began to feel rather good. She removed it and worked a slightly larger dildo into me, telling me to just relax. I did so and was rewarded with new levels of pleasure.
She removed that dildo and placed another at my hole. She pressed firmly and then said, "push out, as if you were going to the bathroom."
I did so and felt it entering me. I relaxed more to take it in more easily and it felt very substantial, but enjoyable.
"That is about the size of many cocks," Helen said, "if you ask them to go slowly, you should be able to take it with ease."
Helen told me to hold the dildo in place and she put on some sort of device with straps attaching a dildo to her. "This is a strapon – it allows me to fuck you as a man would."
"I don't think I can handle something that big," I said.
"You already are," responded Helen, "just relax and you'll have no difficulty."
Helen positioned herself behind me and took the dildo out, and quickly pushed the strapon into me. She was right that it was no larger than the dildo, and I had no difficulty taking it in.
Then Helen began to stroke in and out of me – it felt a lot different than when she was moving the dildo by hand. Strangely, I thought I could feel her passion in the thrusting and I liked it. She continued to fuck me and soon cried out, and then stopped and pulled me close to her.
She pulled out and cleaned me up with the wash cloth.
"Was that what a real fuck will be like?" I asked.
"Pretty close," Helen replied, "the time will vary because some men cum more quickly than others."
"It almost seemed like you climaxed," I said.
"I did!" said Helen, "this is a special strapon designed to fit my anatomy. Because it aroused me and makes me cum, the fuck is much more realistic than someone just plugging your ass!"
She told me to call her if I needed more help, or if I just wanted another fucking. I thanked her, got dressed and departed.
On the way home I saw the shopping center where I first sucked the cock at the glory hole. I felt drawn to it, and soon was parking my car there. I walked into the mall and to the familiar men's room anticipating the a cock to suck.
I entered the men's room and walked past the stalls to the single urinal at the end. I was disappointed to see the glory hole but no cock. Then I realized that I could suck from the other side, and entered the stall, sitting down to wait.
I put my mouth to the hole, just to try it out, and found that it was positioned perfectly for sucking while seated here. Now I just needed someone to suck.
It seemed like a long time, but eventually someone came in. This was new to me, and I didn't even know what to do – did I just call out and offer a blowjob?
I sat silently as the man came to the urinal and took a leak. I watched him the entire time, and he must have seen my mouth at the hole, because soon he was bringing his cock to hole. I was surprised, but eager. I backed away from the hole, allowing the cock to enter.
I was thrilled to see the cock come through the hole, offering itself to me. I took it in my mouth and sucked as I had been taught. Still new at this, I was getting the hang of it, and soon he was cumming in my mouth. He thanked me and left. I felt a wonderful sense of accomplishment.
I continued to sit there, waiting for another. I knew it was getting late, so there would be few people coming in. Just the same, I waited, hoping for another. I patience was rewarded and another man came in, using the urinal. As before, I kept my face at the hole and the man turned to offer me his cock. I sucked him, and soon received his warm load.
He pulled out and thanked me, saying, the mall will be closing soon, so it's time to leave.
I waited to hear him leave, and then got out, washed my hands and left. A security guard was standing nearby and approached me. I was immediately concerned, feeling like I had been caught.
"You do good work," he said, "I hope you will be here often. Here is one of my cards. Feel free to call if you want some more."
I thanked him and left, relieved that I had not been busted.
–––––––––––– –––––––– To be continued ...
Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)
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