Letters to Penthouse VI (37 page)

When my girlfriend Delia told me she was leaving me, I thought I wouldn't be able to live without her. I knew that I had to get her back to survive. I decided that I would do anything—even beg if necessary!

I met her for coffee one Friday morning and explained that I had to have her back. I said that if only we could reconcile, she could call all the shots. She said she would call me at my office by three o'clock and let me know what her decision was.

I waited on pins and needles all afternoon. A minute before three, the phone rang. Delia told me that if I was sincere and truly wanted a second chance, I had to follow her every instruction to a tee. As I had stated that she could call all the shots, I was to go to her apartment and follow the instructions I would find under the doormat.

I immediately left for her apartment. I found the instructions where she said they'd be. I let myself into the apartment before reading them. The first line read, “Shave off all hair!” I thought, Hell, no! But as I read on, I saw that she had stipulated that I only had to shave below my sideburns, and I breathed a small sigh of relief.

My next thought was that there was no way that I would let her do me this way. Then, suddenly, I realized that maybe I did have a chance to win her back. I figured that no one but us would ever know and that it might even be fun to win her back this way.

On the kitchen table I found a pair of scissors, a can of shaving cream, a razor and a bottle of Neet. There was also an envelope with my name on it. Of course, more instructions were inside. I was told to go to the bathroom and “comply fully” with the additional instructions I would find.

In the bathroom I found another envelope with the message “Open only after the first step is completed!” on the front of it. I really didn't want to go through with this dumb request, but I knew that I'd never win her back if I didn't. Slowly and very, very, carefully, I shaved off all my body hair. I felt really naked as I stepped out of the shower, my task finally completed. I felt like a guy who had forgotten to zip his fly and didn't have any underwear on.

I read the next set of instructions, which informed me I was to go into her bedroom and jack off into a washcloth she'd left on the bed. The note stated that she didn't want to see me with a hard-on, so she expected that I would take care of that now, before she came home. She added that if I wanted to back out of the deal, I should leave now. I decided to go ahead with her little game.

Just after I had finished my second task, she walked through the bedroom door. First she laughed and said I looked like the little wimp I really was. Then, with a smirk, she explained that she had video monitors in every room in the apartment and now had a cute flick that she was sure I wouldn't want the guys at work to see. At this point my dick, which had already shrunk down to the size of a pencil, suddenly shriveled down to the size of a tadpole. I knew I was in trouble then!

By now it was six in the evening, and of course she had more instructions. I was told to get my little slave prick into the guest bedroom and stay awake for six hours, jacking off each hour on the hour. She promised to join me at midnight. I followed these instructions only to wake up alone the next morning with a sore prick. She appeared shortly after dawn and told me it was time for another jack-off session. With a big grin on her face, she watched as I brought myself off yet again.

When I was through, she said we were going for a ride to the beach. I couldn't believe my ears. I had shaved off all the hair on my body below the shoulders and this was my reward?!

We drove to the beach and she pulled into the parking lot adjacent to the nude beach, which was a three-mile strip of sand just south of us. She parked and got out for a moment, saying she had a surprise for me. Two minutes later she returned, and we drove south.

Now I sensed that I was in trouble. She drove to the opposite end of the beach and told me to follow her down to the water. She handed me the tote bag and started walking off. I felt I had gone too far to turn back, so I followed her.

About fifteen feet from the edge of the water, she laid out a beach towel. Then she removed her cover-up, revealing that she was wearing only the thong bottom of a skimpy bikini. I handed her the tote bag, and she retrieved a pair of sunglasses and lay down.

She looked up at me and told me that this was a nude beach, so I wouldn't need my trunks anymore. When I protested, she reminded me of the video she had made and the fact that a lot of people I knew would probably love to see it. I grudgingly removed the trunks as she watched, and then she tucked them into the tote bag.

I had never thought that I would be standing on a nude beach, completely naked. The situation felt worse, because here I was, hairless and bare as the day I was born, with a limp, two-inch prick dangling between my legs. I glanced around and realized that I was really out of place. Some of the other men on the beach were sporting nine-inch trophies!

My next instructions soon followed. I was told to walk up to the north end of the beach where we had first parked. I was to locate the pint-size milk container she had left there and follow the instructions inside it.

I turned and headed north to the other end of the beach. I was fully aware of the eyes of both men and women watching me. Some would giggle and whisper to their friends while others pointed at me. The walk seemed endless, but I guess that was because of the circumstances. Being devoid of body hair, and sporting a prick that most teenagers would be ashamed of was rather embarrassing for a grown man like me.

When I reached the end of the beach, I looked around until I spotted the milk carton. I opened it up to find yet another surprise. Inside it was a note with instructions and a ball harness with a dangling tag that said “Slave,” on it. A ring was attached at the base. Underneath it was a temporary tattoo that also said “Slave,” and a moist towelette.

As I read the instructions I couldn't believe it. I was to apply that tattoo to my right ass-cheek and strap on the harness. I looked around to see if anyone was nearby and was relieved to see that the coast was clear.

I complied with the orders and headed back to the southern end of the beach. To my surprise, the harness caused a semierection that I was well aware of. I thought, At least that's better than the two-inch joke I walked north with. I'm not sure if it was my hard-on, the harness or the tattoo that made me feel like I was the center of attention, but I soon found out!

A naked young woman was the first one to approach me. She grabbed me by the harness tag, wanting to see what it read. She got down on one knee to get a better look. As she read it, she smiled and motioned me on, but slapped my ass hard as I passed. To my amazement, this made my prick even harder. I was even more surprised when a lady of forty or so walked up to me and handed me a business card. A note on the back said to call her if my mistress ever gave me up.

When I finally got back to where Delia was lying, she asked me to give her the instructions. I told her I'd put them back in the container, which I had left where I'd found it. She told me that I had made a really dumb mistake and had to go back and get them. She told me to take off the harness and start walking. I started to worry that this thing would never be over. I dropped the harness in her hand and headed north once more.

At the end of the beach I again located the container and retrieved the instructions. I saw that there was yet another piece of paper in the carton. I dreaded what it would say as I pulled it out. I almost cried as I unfolded it. The note read: “Your trunks are buried in the sand about four inches below where you picked up the container. I hope you read this before moving away or you might be searching all night! Don't return without them!”

Well, let me tell you, I was really relieved that I hadn't moved the container! I dropped to my knees, dug in the sand like a terrier and found my swimsuit. I hurriedly put it on, glad to be covered up again. All of a sudden I heard a horn blow in the parking lot. I turned and saw Delia's car slowly headed in my direction.

When she realized she had my attention, she stopped and motioned me over. As I reached the car, she simply told me to get in. As we drove away she informed me that she had thoroughly enjoyed her day at the beach. She added that she was really glad I got all that sun, and that I would probably peel like a snake, right down to my worm!

I glanced down and realized that she was telling the truth. I was as red as a lobster. I had been on the beach for hours, totally naked, and I hadn't even used any sunscreen. To make matters worse, I could feel that the sand in my trunks was only complicating the problem. I was going to pay dearly!

What she said next really floored me. She told me that she had a new lover, and that her lover had made another video of me while I'd made a fool of myself on the beach. She added that I would have to meet her lover sometime, and that it might as well be now. She told me that I'd soon be viewing the tape as well. I was also informed that I was going to be given to a mistress named Vicky.

When we pulled into the parking lot of Delia's apartment, I was instructed to go in and shower. I was to then wait naked in the living room for my orders. I knew that it wouldn't do any good to argue. As I dried off after the shower, I realized that I was badly sunburned. I had blistered from head to toe, and the pain was just beginning.

I waited in the living room as instructed. I'd been there less than a minute when the doorbell rang. Delia told me to answer the door, that it was probably her new lover and my new mistress.

My prick would have crawled up inside me if it could have as I answered the door. You can imagine my surprise when I saw the young woman and the lady in her forties whom I had met at the beach standing in front of me.

Delia explained that the older woman, Brenda, was her new lover, and Vicky was one of Brenda's friends. Brenda was in the process of teaching Vicky to be a real man-hater. The three of them grabbed me and, within seconds, had cuffed my hands behind my back. Vicky opened her purse and pulled out the same ball harness that I had worn at the beach. She encased my balls and attached a leash to the ring that the tag dangled from. Pulling on the leash, she led me across the living room and told me to sit on the floor at her feet.

They turned on the television and announced that it was show time. I was forced to watch myself as a slave, from shaving myself bald to parading down the beach. Then I was forced to watch the three of them have sex with each other. After a while, Vicky stood up and tugged hard on the leash as I tried to quickly scramble to my feet. I managed to stand, and Vicky knelt in front of me, kissed my cock and slowly proceeded to blow me. My prick grew harder and harder, and I was about to explode when she suddenly stopped. I was left with a raging hard-on, and for the moment there was nothing I could do about it.

Vicky pulled me by the leash down the hallway, led me into the spare bedroom and pushed me facedown on the bed. I lay sideways across the bed as two of the three women tied my ankles to the bedposts. The cuffs were then unhooked by a removable link and reattached to chains on the opposite side of the bed. Next two pillows were placed under my hips and a four-inch vibrating dildo was greased and shoved up my ass. One of the women turned it up on high just before they left the room. I lay there with a throbbing hard-on and a stuffed ass for who knows how long. It seemed like at least three hours had passed, and I wondered if the batteries would ever run out.

Vicky finally came back into the room by herself. She asked if I thought it was time for her to take the dildo out. I told her that it was way past the time. She walked around in front of me and slowly stripped off the robe she was wearing. She opened a dresser drawer and pulled out a six-inch, strap-on dildo. As she strapped it on, she said that it wasn't time for the vibrator to be removed, but time for it to be replaced. She then pulled out a cock-shaped gag and ordered me to open my mouth. I kept my mouth shut in protest, so she reached over and spanked my sun burnt ass with her bare hand. Needless to say, a small plastic prick was soon shoved into my mouth and secured around the back of my head with a cloth strap.

She asked me if I had ever fucked a girl up the ass. I knew that Delia had probably confided in her that I had, so I nodded. Next she asked if I had ever wondered what it felt like to be screwed that way. I could only shake my head no as she pulled out the vibrator. She said it was high time I found out what it felt like.

When she went to plunge the dildo in, I realized she hadn't even lubricated it. I muffled a scream as she invaded my backside. Tears began to flow from my eyes as Vicky tugged on the leash of the ball harness and shoved the dildo in to the hilt. She fucked me for what seemed like an eternity.

When she finally got bored of this, she removed the dildo along with my gag. She turned around and instructed me to kiss her ass to show my appreciation for losing my anal virginity. After I kissed each cheek, she said she would see me in the morning and left. As she closed the door she told me to get a good night's sleep.

I was left facedown, spread eagle, and with the ball harness and leash still attached. I have no idea how long I lay there like that before finally falling asleep. It must have been most of the night, because I didn't feel well rested at all when I was awakened the next morning by Vicky.

My hands were reattached behind my back and my ankles were freed. I managed to get to my feet, and I was led by the leash back into the living room. While I walked I felt a soreness in my ass and an aching in my balls. I glanced down and realized why my nuts hurt so bad. I still had a raging hard-on, and my nuts were full and trying to break free of the harness. I wondered if I would ever get any relief.

As we entered the living room, I saw Delia and her new lover fondling each other on the couch. I was taken to the center of the room and instructed to stand still. The leash was then removed from the harness and Vicky told me to turn around, which I did. My back was now to the couch. Vicky informed me that the temporary tattoo would be replaced by a permanent one just like it. She said a tattoo artist would be over around two that afternoon.