tagExhibitionist & VoyeurRick's Embarrassing Adventures Ch. 02

Rick's Embarrassing Adventures Ch. 02


Chapter Two--Contract And Adventure

Rachel's bra did fit. She put a couple of pair of her sport socks in each cup "to fill it out" she said. In the mirror, I looked like a guy with a striking pair of boobs. They wouldn't stand up to close inspection, of course, but I felt very embarrassed wearing a filled out bra. Of course, Rachel took a couple of pictures of the guy with the hard dick and full bra.

Then she led me downstairs to the living room. She put a towel on her sofa and sat back with her legs spread while I knelt before her and ate her out while she played with her tits and nipples. As she got closer to climax, she grabbed the back of my head and pressed my face into her pussy, humping my nose and tongue while I tried to breathe while continuing to tongue fuck her. She had quite a climax and was a few minutes regaining her full senses.

She finished off the evening with a couple more pictures of me, with her juices all over my face and a hard, untouched cock all in plain view. Once she was happy with her pictures, I dressed in my casual shirt and slacks, socks and shoes. I had to carry my underwear. "None of that man stuff for you," she declared. "Go commando until I get you some nice panties." A couple of more pictures, and I was out the door while she scurried off to visit the story site I had told her about.

I went home with instructions to drive the speed limit and obey all traffic laws and undress completely once I got home. "But under no circumstances are you to cum outside of my presence without my express permission." I, of course, agreed with a "Yes, ma'am. Thank you, ma'am." Once home, I fell asleep and dreamed of horribly embarrassing, yet highly erotic situations in which I was shown off to all sorts of people.

Of course, I woke up with a raging hard on, but I remembered my instructions and willed it down so I could pee and get a shower and shave for the day ahead. The day ahead. What did Rachel have in store for me today? I'm already feeling randier than I can remember since I was a teenager. How long would THAT last? Not that I was complaining. I wondered if I had discovered the fountain of youth in my weird fantasies.

I didn't have much to do that Saturday morning. When I left for work the day before, I knew I was meeting Rachel for dinner and ... after work, and I expected to wake up in her bed this morning. Yes, we actually called our trysts "dinner and..." We weren't a couple exactly. We were friends. Then one day we decided to sleep together. So we became friends with benefits. But we dated others; we slept with others. We had our own lives. But we were first and foremost friends.

Now we were...what, exactly? I didn't know, but I was excited to find out how this was gonna work out. I was also, I admit, scared. Could I go as far as I wanted? Could I go as far as she might push me? Might she give up because it just wasn't something she wanted to do? Or had I unleashed a tigress? What I saw last night in her resolve made me wonder what I had gotten myself into.

I started to think about what I wanted in a contract with Rachel. I honestly wanted the experiences I had told her about. One one level they terrified me; on another level they excited me like nothing has in a long time. I wanted it to last at least a month. Frankly, I figured that with our work schedules, we probably couldn't do much other than on weekends. So, counting this one, we had four weekends. That meant a lot of work for Rachel to schedule my activities, which I fully expected her to be around for. She was both my security blanket--someone who would be there with me when I was scared or got into trouble--and my taskmaster (mistress?) who would insist I not wimp out but complete the embarrassing challenge ahead of me. I began thinking maybe we would need to spread this out over a couple of months to account for real like.

I was still thinking in this vein at ten o'clock when Rachel called. She wanted to know if I had anything I wanted to add to what I had said last night. I told her that I was worried about how little time we'd actually have, given our hectic schedules.

She cut me short. "Scheduling is not your concern. I've laid out a program that should fit both of our needs and schedules, unless you have something coming up you haven't told me about."

"No, ma'am," I answered. "You have access to my schedule, and I have nothing coming up that I am aware of. Of course something might come up, but I'm not expecting anything."

"Neither am I," she answered. "If something changes, we'll discuss it at that time. Now, if you have nothing else, I'll email the contract I've drawn up. You will send me your address books, both work and social. Once you get here, we'll discuss any changes that you feel need to be made. Do keep in mind that I read those stories you pointed me to. They were fascinating and gave me some wonderfully wicked ideas."

My heart sank a little even as my cock rose. There were parts of those stories that I didn't think I could do. The stories were about a woman who wanted to be used as a slut. She would suck and/or fuck anyone anytime for the man she had given herself to. He, in turn, would tell her to find strangers and blow them or fuck them in public or semi-public places. I'm willing to believe a woman can pull that off, but how many guys will let another guy blow them, even in private? And women who are strangers? Well, I'll concede it's remotely possible, occasionally, in exceptional circumstances. Routinely? No way. I'll be lucky if I'm not arrested and with most guys I'm likely to get beaten up.

Still, I trusted Rachel. She knew all the things I knew. I didn't think she wanted me to get arrested or beaten to a pulp. So I just said, "Yes, ma'am. Thank you, ma'am. I'll send my address books right away."

She hung up with a lilt in her voice as she said, "See you at noon, Richard."

I went into my office and fired up my computer, which immediately told me I had mail. Among the usual pieces of this and that was Rachel's with attachment. I resisted the urge to open it until after I had downloaded my address books to a text file and sent them to her in a separate email. Then I opened her email.

Hi Rick,

When you open the attachment, be sure to put

your full legal name in the blank at the top.

You will see my full legal name in the

appropriate spot after your name. In addition

to the other items you are supposed to bring,

print out two copies of this agreement

and bring them with you.


I opened the attachment and saved it to a file on my computer. Then I read it.

"Personal Services Contract Between ___ and Rachel Irene Marie Simpson (Rachel)"

No, I hadn't known her two middle names, and I must admit that I laughed when I saw what the initials spelled.

I added my own, rather more mundane, name: Richard Thomas Thornton III (Rick). Then I read on.

"Rick grants Rachel access to his body for any and all sexual services she may require of him with herself or with anyone else who she may designate. Rachel agrees to make any and all sexual activities with Rick as embarrassing and humiliating as possible consonant with keeping Rick safe from permanent bodily harm.

"Rachel further agrees to find ways to humiliate and/or embarrass Rick both privately and in public provided Rick is not exposed to legal arrest or imprisonment. Rick has requested this service of Rachel and she agrees to provide it. Rick further agrees to allow Rachel to photograph and/or video any of his activities for her exclusive use.

"Should Rick fail to attempt any task set for him to perform, he grants Rachel permission to reveal to any or all of Rick's friends this contract and any pictures or videos she chooses to release. Should Rick complete all assigned tasks, Rachel agrees to give him all copies of this document and any pictures or videos of his activities or to destroy them in his presence.

"This agreement is in effect from today, 25 June until 25 July and can only be modified by mutual consent of the undersigned."

Well, I thought, that's pretty succinct...and pretty sweeping. I printed out the two copies. I could think of a lot of qualifiers and disclaimers I might want in this document, but I decided to go with it as written. Rachel knew that I wanted to live some experiences that were in those stories we had now shared. I knew I would be very uncomfortable, but that I had asked for it. So I had no kick coming. As I drove off to Rachel's, I wondered briefly what lay at the end of this road. There was no telling, but I was sure it would be exciting.

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