Letters to Penthouse V (4 page)

He started begging me to stop, and yelled uncle repeatedly. I made him say that I was stronger than he, and that he would pay off the bet and be my slave. I also made him say that he would masturbate and also suck cock. Not only did I make him say it, I made him beg to masturbate and beg to suck as many cocks as I wanted. When it got to the part about sucking cock he hesitated, but I said, “Come on, sweetie, it could be worse. I licked my middle finger and jammed it up his ass. He got the point, and started begging to be allowed to suck cock and swallow sperm.

I had an orgasm just listening to him begging to eat come. I let him up, directed him to kneel in front of me on top of the coffee table and made him beg for permission to masturbate. Harlan said, “Please let me masturbate for you. I want to stroke my cock for you and eat my hot come.” I told him to start masturbating.

Every time it seemed that Harlan was almost coming I made him stop, lick the drops of come that had collected on the end of his cock and tell me how he wanted to suck cock. I finally let him come, catching it in my hand. After he begged to be allowed to eat it, I made him slowly lick up every drop.

Having planned this event for some time, I had already purchased women’s clothing, makeup and a wig for him to wear. I dressed him up in his sexy new attire—garter belt, stockings, bra—the whole nine yards, except that I wouldn’t allow him to wear panties.

I took him to the gay bar, where we met up with a gay black friend of mine. I enlisted my friend’s help, and before the night was over he arranged for Harlan to suck off five guys in a back room of the bar, including sucking off my friend twice. It was the greatest sight watching Harlan, on his knees, kiss, lick and finally suck a cock. I made sure everyone came in his mouth, and that he swallowed every drop.

For the rest of the weekend I either kept him naked or in a frilly French maid’s outfit that kept his ass, cock and balls exposed. On the second night I invited three girlfriends over (Cleo is actually a transsexual, but she looked hot, especially her cock, which I saw for the first time that night). I dressed him in a French maid’s outfit for the evening. I made him masturbate for us and eat his come, but only after begging.

Then I was ready for some real fun. I told the girls how much Harlan liked sucking cocks, and they wanted to see Harlan work on Cleo. Since they all knew of Harlan’s previous taunting of gays they were going to have some real fun. Cleo dropped her dress and stood there wearing only a pink garter belt and stockings. With her firm tits, small waist and tasty cock hanging between her legs, she looked great.

The girls told Harlan to kneel in front of Cleo and beg to suck her cock. We all loved watching his humiliation and made it as embarrassing as possible for him.

I had never seen my girlfriends this excited before. They said that if his begging wasn’t good enough, they were going to spank him. He begged and pleaded to suck Cleo’s cock, but the girls decided to spank him anyway. While begging he said, “Please let me suck your big, beautiful cock, please, I beg of you, let me suck your big, hairy cock, please let me suck your cock and taste your hot, sweet come.” After some more begging we had him kiss and lick every square inch of Cleo’s cock. Then the girls told him to take Cleo’s cock in both his hands and suck her off. When Cleo came, she shot part of her load in his mouth and the rest all over his face, spreading it around with her cock.

I made Harlan swallow the come in his mouth, but had him leave the rest on his face for the entire evening. One of the girls told Harlan that for the privilege of being allowed to suck Cleo off, Harlan should show his appreciation by kissing and licking Cleo’s asshole.

The girls told me that that was the most exciting and sensual night of their lives. They loved watching Harlan’s humiliation, and they all asked if they could return for some more fun with the “sissy.” Of course I said they could use Harlan anytime and any way they wanted to, and the girls have been over frequently, especially Cleo.

Since that first weekend, Harlan has been my slave. Being able to live out my fantasy took some initiative and careful planning, but it was well worth it.—
L. M., Biloxi, Mississippi

YOU’RE NOT TOO OLD TO BE TAKEN OVER MY KNEE

I moved here from England ten years ago, when I got married. My wife Liz had a nine-year-old daughter. England has a long history of spanking for discipline. My wife didn’t believe in it.

My stepdaughter Bonnie is now nineteen and has been away at college for the past year. She came home on break recently, and brought her roommate Moira. On Friday night they stayed out until three in the morning. Saturday my wife and Bonnie had a fight, as her curfew is one o’clock.

I told her that, regardless of whether she was right or wrong in her argument, she had to control her temper or she’d get the spanking she was so long overdue for. She said I wouldn’t dare.

Bonnie normally sleeps in just a T-shirt and panties, so when I grabbed her and pulled her over my lap, she had little protection. When I gave her her first spank, she really started cursing at me. I stopped (keeping my hand on her panty-covered bottom) and calmly said, “If you don’t stop, I’ll take your panties down and really let you have it.”

Again she told me I wouldn’t dare, adding, “You’re not my father.” That stung, and I was determined to sting her in return. I pulled her bikini panties right off, exposing her round little bottom. She squeezed her legs together so I couldn’t see anything, but I knew that a few well-placed swats would soon change that.

I lectured her first, and then really began spanking her. After about a dozen slaps she started crying and kicking her legs, begging me to stop. Her bottom was turning a pleasant shade of red, and I was really getting turned on by all her squirming. It had been a long time since I’d administered a good spanking, and I was enjoying myself immensely.

I was equally enjoying the sight of her pussy lips, which were now in plain view, as red and swollen as her white cheeks were becoming. As I continued to spank her, I noticed that her lips were getting moist, as I had hoped they would, and she was moaning. Just when I was getting well into the game, though, she started to apologize. It was unbearable to me to stop, but there was really no excuse for going on, so I withheld my hand, and stood her in the corner.

While all this was going on, her friend Moira had been yelling at me and calling me names, saying she’d have me arrested for assault. I told her if she didn’t mind her own business she’d get the same treatment, hoping of course that she would ignore my warning. I wasn’t disappointed. She continued swearing at me.

When I finished with Bonnie I grabbed Moira, a small blonde, easy to turn across my knee. Moira was wearing a nightgown, and when I pulled it up to her waist, I found she wasn’t wearing any panties. As I began spanking her, her pale white skin quickly turned red and she continued to twist and wiggle, trying to escape. Nonetheless, it was soon clear that she too was aroused by my efforts, as the very strong smell of her pussy juice told me.

She was much more stubborn than Bonnie, and ended up being spanked much longer. At first Moira didn’t want me to know she was enjoying herself, but after a while she abandoned her attempt to hide her pleasure and began openly humping my knee. She continued crying and kicking, but her hard, fat clit was pressed against my leg and she bounced up and down instead of twisting and trying to get away. Before I finished she had an orgasm, and her juices flowed and left a wet spot on my pants.

I stood her in a corner also, and told them I wouldn’t release them until they stopped crying and apologized. The sight of these two shapely young girls rubbing their sore, red bottoms was a sight to behold. Bonnie asked me very humbly if she could put her panties back on, but I told her no. They both held out a little longer, but soon Bonnie, and then Moira, apologized very contritely. I let them go about their business, while I ran back to my bedroom to release my own pent-up tension.

Later, Bonnie and my wife went shopping. Moira stayed home to rest. I was out by the pool when Moira came out wearing a skimpy black bikini. She asked me to rub cold cream on her tender bottom and suntan lotion on her back. She managed to lie in the sun, but only on her stomach, as her bottom was so sore.

Since this first episode, they have both come to visit again, and both have found ways to force me to give them spankings. Not that I need forcing, you understand, but there’s something to be said for maintaining the illusion. My wife now agrees that we should have used spankings to punish Bonnie years ago. Bare-bottom spankings have become the standard punishment in our home.—
G.W., Galveston, Texas

TWENTY-FIVE LESSONS ON HOW TO BE A BETTER HUSBAND

I’m thirty years old and have been married to Reggi for seven years. Recently Reggi found out that I have been fucking my twenty-four-year-old secretary. Reggi is exceptionally beautiful, and we have a great sex life, but I couldn’t resist Liza, and had been fucking her for about eight months when Reggi found out.

Reggi and I make love about four times a week. Reggi loves sex, will always try new positions and never refuses to suck my cock. When she found out that I was fooling around, she went crazy and threatened to leave me, I begged her to stay, and told her I would never do it again. After a lot of begging, Reggi said she would stay, but insisted that she first had to get even. I was to be punished by having no sex for thirty days. In addition, since I really need Liza as my secretary, Reggi said that I could keep her, but Reggi wanted a little chat with her. She also told me that if it happened again she would be gone immediately. The expression on her face let me know that she wasn’t joking.

My punishment started. I was forced to sleep in our extra bedroom away from Reggi. In addition, Liza couldn’t speak to me except about business. During that month, Reggi was often not home when I got home from work. She usually arrived home at two or three o’clock in the morning. In addition, Reggi told some of my co-workers about my situation, and I was the butt of their constant jokes. My affair with Liza was well known in the office, and I suspect one of my co-workers was responsible for Reggi finding out.

The night that my month of punishment was over, Reggi handed me a large box. I opened it, and inside were about twenty-five videotapes. Reggi sat down with a smirk as I put on the videotape. The tape showed Liza, completely nude, lying facedown on a bed, and Reggi standing over her, fully clothed, whipping her ass with a riding crop. Liza was telling Reggi she would be good and never fool around with me again.

When Reggi stopped whipping her I was very surprised to see three of my co-workers—Glenn, Stevie and Billy—appear on the screen. They started to strip, and Reggie told them to fuck Liza up the ass. Liza was begging them to please be gentle, as she had never been fucked up her ass. Reggi smacked Liza again with the riding crop and told her to beg to have her tight asshole fucked. Liza was facedown with her butt in the air when Glenn got behind her and started to penetrate her asshole. It took at least twenty minutes of Glenn’s thrusting for him to get his cock all the way in. I could see that Liza was finally starting to relax and had begun to enjoy her reaming. Glenn stroked on until he shot his come all over her back.

Stevie was next. He was able to slide his cock right into her ass. He talked a lot, telling her how tight and hot she felt. He said he’d wanted to do this for a long time, and had been saving a load for her all week. When he came, you could see that it was indeed a big wad. By now Liza was begging for more.

When Stevie was finished, Billy had his turn. Liza was begging for his attention, and before he stepped up to her there was a shot of her asshole, which had remained wide open after Stevie was finished, come dripping out of it as she panted, thrusting her hips back. Then Stevie plugged her hole, and in a few minutes Liza received her third dose of sperm of the evening.

In the final scene, Liza was in between Glenn, who had his cock in her pussy, and Stevie, who had his cock in her ass, while Billy shoved his dick in her mouth. All of Liza’s holes were filled, and she was mumbling for them to fuck her hard. After they came, the camera zoomed to a shot of Liza’s very red asshole with four loads of come dripping out. The tape ended, and I realized that I had a huge hard-on. I was also grateful that Reggi had kept her clothes on. It would be hard to go to work if my wife had let my co-workers fuck her.

Reggi told me to put in the second tape. My joy about Reggi keeping her clothes on was short-lived. The second tape began with Liza, lying on my desk naked, and Reggi, completely nude, wearing a huge strap-on dildo. Reggi looked right at the camera and said it was her turn to fuck Liza’s tight little ass. She positioned Liza so that her ass was facing the camera and pushed the dildo halfway in. She stopped and asked Liza, “What do you want?”

Liza shouted, “I’m a slut, and I want my ass fucked.” Reggi accommodated her, ramming the rest of the dildo to the bottom in her asshole. Reggi was giving Liza a tremendous fucking, which actually caused Liza to have a wrenching orgasm. After Liza came, Reggi withdrew from her ass. She took the riding crop and whipped Liza a few times on the butt, then told her to get her sorry ass out of there. Reggi lay down on my desk and spread her pussy for the camera.

That’s when my co-workers appeared on the screen. My worst fears had been realized. There was Reggi getting the fucking of her life from three guys on my desk in my office. Glenn, Stevie and Billy each took turns fucking her pussy. She also gave them each a blowjob, letting them come on her face and in her mouth.

All of this had a strange effect on me. When the tape was over I was so horny that I went over to Reggi and ripped off her clothes. When I got to her panties I saw that she had completely shaved her cunt. I wanted her pussy so much I didn’t stop to think about it. I rammed my dick into her bald hole and came very quickly.

After I came, she sat on my face and had me eat my come out of her. I continued to lick her for almost two hours, during which time she had half a dozen grinding orgasms. We finally calmed down and went to bed. Before we went to sleep she told me that over the next few days I would have to watch every single video, including the one where her pussy had been shaved.