The Season’s Greetings. The third and final man-substitute looked to be a homemade relic. It was a glazed ceramic Christmas tree, complete with ornaments and star on top. At first I thought this was a carelessly placed ornament, but on closer examination it appeared to still be in considerable rotation.
This poor gift looked both fragile and weathered. It had hairline fractures running longways and was discolored various shades from tip to base, like rings of a tree or waterlines on a seaward limestone cliff, where you could tell how close this poor imitation of seasonal tidings had almost been swallowed whole.
You’ll be happy to know that I never engaged in vaginal intercourse with my roommate, although I did yield to the occasional perfect storm of me coming home obliterated and her unconditional willingness to prove to me how good English girls were at giving sloppy couch head while we watched Save the Last Dance for the third time that week.
I imagine fucking Alessandra might have been the equivalent of inserting your cock in a bottomless receptacle the diameter of a gallon paint can, only filled with a combination of eerie guys she’s come into contact with. I just assume her vagina was better suited to being worn like a cowboy boot. The adventurous are issued helmets with spelunking lights and are required to have no less than three years of base jumping experience prior to entry.
I shouldn’t be so harsh though. I’ll never know the answer. Perhaps it secretes a wonderfully hypnotic tonic that captures its prey, and has their heads swimming in lust and desire. Since she has a steady stream of callers there must be something that keeps her snatch chock full o’ cock.
But for me, I have to say I do miss the head. Orally speaking, she sucks!
—G.R., Greensboro, North Carolina
If a Lady Asks You to Plug Her Butt, What Can a Gentleman Do?
I own my own contracting business, and one day I get a call from a wealthy lady who wants me to build a deck onto her house, next to her pool. So I go over there to take a look, and once she agrees to the price I tell her I can start the following week.
Now this lady is really hot. Long blond hair almost to her butt, which I might add is gorgeous. She’s only five feet two and maybe 100 pounds soaking wet, but it’s all curves, and sexy ones at that. Myself, I am six feet four and 235 pounds; I work out a lot, and get some pretty hot babes sometimes. But this chick is really special.
So the next Monday I’m back there starting the job, and out of the house comes this walking sex dream, her name is Ginny, by the way, wearing a freaking G-string and this tiny top that barely covers her bulging C-cups. She then lies down in a chair about ten feet away from me. Like I’m going to get any work done now.
She sees me staring at her and smiles. Then she asks me if I need a break. Well, I’ve barely started, but shit yeah. So I go over and sit next to her, and she asks me if I’d like to take a swim. Sure, but I don’t have a bathing suit, I tell her, and you know what she says? “So what?”
Okay, fine. So I strip down. Then she stands up and takes off her bottoms, and I’m staring at a very nice shaved pussy. I jump in the pool to hide my hard-on, but I think she has seen it anyway.
So she gets in the pool, too, and we are goofing around when suddenly she moves in front of me and slides that butt across my crotch. I grab her from behind and start rubbing her boobs, and I feel her hand on my hard shaft. Okay, no more fooling around. I lead her out of the pool and onto the deck, where I bend her over a chair and slide inside her.
Ginny gives a gasp of pleasure, and we are having a great time when all of a sudden she asks me breathlessly if I would mind using a butt plug on her. What the hell, it’s her butt, and that’s what I tell her. She takes off then and runs into the house, and when she comes back she hands me a butt plug.
Well, this is something I’ve never done before, but I’m game. Ginny tells me to insert the plug after I slide my cock back into her pussy. So I slip back into that sweet wet honeypot, then take hold of the plug and slide it slowly into her butt.
Christ, I get so hard I think I can feel her belly button, and as for Ginny, she’s screaming and bucking and coming all over my shaft. I ride that lady hard, and when I tell her I’m going to come, she pulls me out, turns over, and tells me to shoot all over her tits. Which I do.
Sometimes I really love my job.
—L.R., Oklahoma City, Oklahoma
She Wasn’t Who They Thought She Was, but She Wanted to Be
I am a 35-year-old single woman, a blue-eyed brunette with a petite body and a pretty face. I have a job that requires me to attend trade shows about twice a year.
Recently, attending a trade show in Chicago, I got into conversation one evening with a group of four men who claimed to have met me before, although I didn’t recognize them. They kept calling me “Ann,” and I soon gathered that they had taken me for some woman who had had sex with them in a hotel room the night before. At least that’s what they claimed, although this seemed very strange and suspicious to me. The men were very blatant with their sexual innuendos about Ann. They were soon giving me graphic descriptions of the things they had done with her. Although I tried to assure them that they had the wrong person, they wouldn’t listen. I didn’t know if they were playing some kind of game with me or what, and finally I simply walked away.
I had heard about women participating in such gang bangs, and in fact I had had secret fantasies about being the only woman in a roomful of men. The things the men had said had actually aroused me, and to regain my composure I went up to my hotel room and took a hot bath. I began to shave my legs, and then I got so carried away that I lost all inhibitions and found myself shaving off my pubic hair. For some reason I was suddenly obsessed with a desire to fulfill my own secret fantasy.
I got out of the tub and dried off, then put on a white silk evening dress. The dress was so sheer it was nearly transparent, but I didn’t bother with underwear. With my pussy drooling, I made my way to the hospitality suite where I had encountered the four men earlier.
I couldn’t see them as I looked around the suite, so I went to the bar to get a drink. I could see a number of men staring at me. I was wearing open-toed high heels, and my bare toes made it obvious that I wasn’t wearing stockings. My bloodred areolae and my erect nipples could be seen through the dress, and left no doubt that I was naked beneath it. The women in the room gave me suspicious looks, but the men were smiling.
The young, cocky bartender stared at me as hard as anyone, and when he served my drink he told me his name was Dave, and boldly asked me if I’d be willing to go to his room with him and his buddy Mike, who was working the snack table. I was actually somewhat turned on by his brazenness, and not seeing any of the guys I’d met earlier, I accepted.
Dave quickly found two guys to fill in for him and Mike at the bar, and we headed for his room. There, without formalities, the three of us stripped naked. Dave was only a few inches taller than me, but he had an impressively large cock. Mike’s prick, I thought, was the perfect size for me to take on in a double fuck.
I didn’t care about anything anymore except what I’d come there for—cock. I dropped to my knees to suck the both of them, and I did, swallowing every drop of their come and savoring the taste. I expected to be fucked then, but Mike had me lie on the bed and proceeded to go down on me. I spasmed and had a series of mini-orgasms as my clit was licked and nibbled.
But Dave was impatient to fuck me, and soon both of them were giving me the down and dirty sex I hungered for. I had Dave lie back as I mounted his big stiff prick. Then, looking over my shoulder at Mike, I said, “You too.” He lubed himself up and worked himself into my ass, and within minutes we’d established a fucking rhythm.
I really got into taking on their cocks, and I sucked and fucked wildly as they came on me and in me. After a while Mike was fucked out, and sat down in a chair, watching me take Dave up my ass as I lay prone across the bed. I was in seventh heaven with a hard cock buried in my ass. I watched Mike trying to get it up a
gain, but he couldn’t. Then after a while Dave couldn’t either. But I wasn’t ready to stop. I was fixated on cock and I needed more. I was a bitch in heat, and I didn’t care what the guys thought of me. I saw that they were bewildered and maybe a little frightened by my intensity, which probably didn’t help in their efforts to get themselves up.
The ringing of the telephone startled us. Mike answered it, and after listening for a moment he turned to me and asked, “Is your name Ann?”
“No!” I said, and grabbed the phone from his hand. I knew it had to be the guys from before. “How did you know I was here?” I said into the phone.
“Somebody at the suite said he saw you leaving with the bartender,” a male voice said. “Sorry we missed you, Ann. Can we come up and party?”
“Yes,” I said, and hung up the phone.
I took a quick shower and was wrapped in a towel when the knock came at the door. Dave opened it to admit the four men.
Nobody bothered with greetings. I dropped my towel as the men stripped naked. They were obviously as turned on as I was. In a minute I had four hard cocks coming at me. One of the men grinned and said, “Ann, you shaved your cunt.”
“I’m not Ann and you know it,” I said. The man just laughed and lay down on the bed, telling me to get up there and ride his hard cock. I mounted him and took his big dick inside me. He grabbed my butt and pulled me all the way down. The other men gathered around. “You’re gonna get all the cock you want tonight, baby,” one of them said. I could only hope he was right.
The man on the bed had fantastic stamina, and kept his hard cock inside me as I sucked the other three guys in turn. Then one of them got behind me and took me in the ass. I was taking on three cocks at once, and I loved it.
I sucked dick and rode cock and got butt-fucked for as long as those men lasted, taking two or three at a time, or sometimes just one as they continually switched around, finally experiencing nearly continuous orgasms as one cock was replaced by another.
Finally they had to take a break, and I went to take another shower. I couldn’t believe it when I came back and saw two new guys there, already naked. I heard Dave telling them that this fucking nymphomaniac had taken on half a dozen guys already.
I knew I should protest, but I could feel my juices flowing again already. One of the new guys sat down on the bed and told me to get my pretty little ass down there so he could fuck me. How could I say no?
I lay down and spread my legs for him, exposing my well-fucked, sperm-saturated cunt for his pleasure, and mine. He got on top of me and was soon fucking away. His friend straddled my head and stuck his dick in my mouth. I felt myself coming again.
An hour later all the guys were gone except Dave and Mike. Dave helped me get dressed, and as I was leaving he rather sheepishly called my attention to an ice bucket on the dresser. It was full of 20- and 50-dollar bills that the men had left for me.
I didn’t know whether to laugh or cry. I told Dave to keep the money for his college expenses. I may be a fucking nymphomaniac, but I’m not a whore.
—Name and address withheld
He Came as a Cop, She Came as a Catwoman, but Who Won?
“Fuck!” I yelled as I felt my balls tighten. My cock was buried deep inside the cunt of another perfectly boring bimbo, who was straddling my hips as she bounced up and down. I looked up at her face as I shot into her, her name already escaping my memory. She had her eyes closed as she rode my cock, her head tossed back, her large tits bouncing in front of me, her long blond hair tumbling down her back. She was just another girl in the long line of ladies who my brother had hooked me up with. This one was a bartender who worked nights at some bar he went to after work sometimes.
It wasn’t that she wasn’t good-looking. She was certainly very attractive, and I had to admit she had given me a good time. I had definitely come harder with her than I had with the last few girls Jake had thrown my way. But still I just felt detached.
The girl was coming now, and I could feel the muscles of her pussy gripping my cock as she writhed about on me. Then she rolled off and lay down beside me, trying to cuddle as close as she could. I dutifully put an arm around her, but I was already planning to leave her with an empty bed before the sun rose. Dealing with the morning after was just never my strong suit.
I had been working for a leading accounting firm for the last five years. It was a big company, with over 1,000 employees, and I was absolutely positive that no one in the firm even knew my first name. Not that I really expected people to notice me; there’s nothing spectacular about my appearance, and I do tend to keep to myself. I’m five feet nine, with dark brown hair that I keep short and neat, a clean-shaven face, and a body that’s okay, though not as muscular as I would like. I’m not ugly, just not exceptional enough to capture people’s attention. At 37 I am pretty much a confirmed bachelor, and my simple but quite comfortable lifestyle suits me just fine. I don’t have a lot of friends, but I am close to my family, especially my brother Jake, who works for the police department and seems to spend most of his time trying to set me up with girls.
The Monday morning after my night with the female bartender, I walked into my cubicle at work just like always, sat down at my desk just like always, and logged into my mailbox just like always. Today there was a companywide memo announcing the annual company Halloween masquerade party. I didn’t remember there having been any company masquerade parties in the past, but maybe in previous years I’d just deleted the e-mail without reading it, as I often do. But for some reason the idea of a masquerade this year excited me. Maybe it was time that I went out and socialized with some of the people I worked with, and what better way to do it than behind the facade of a costume?
As the day of the masquerade approached I began to get second thoughts. Did I really want to go to the bother of finding a costume and making an effort to socialize with a lot of people I didn’t know, at what would undoubtedly be a very dull affair? When I mentioned the party to Jake, he insisted that I should go, and he even came up with an idea for my costume, offering to lend me one of his old uniforms, so that I could go as a police officer.
The party was held on a Friday night at one of the big hotels downtown, only about five blocks from where I lived. At eight o’clock that evening I was standing in front of my mirror, looking at myself in my brother’s uniform. Although Jake was older than me, I had a slightly larger build, and the short-sleeved blue shirt stretched across my chest a little too tightly, making me feel more like a male stripper than a policeman. I had to admit, though, that I got kind of a kick out of having handcuffs and a nightstick in my belt, and a fake gun on my hip. It gave me a feeling of power.
Well, what the hell, I thought. Maybe I would end up taking a girl home for the night. Everyone always got drunk at these parties, and I was sure she wouldn’t remember me any better the next day than I would remember her. In any case, I planned on taking full advantage of the open bar.
When I walked into the hotel ballroom I was surprised to see how many people had really gone all out in putting together their costumes. As I made my way through the crowd I recognized a couple of women from my department, dressed up as French maids, complete with fishnet stockings and black spike heels. One of them was married, which didn’t interest me at all, and the other was known to have slept with a lot of guys in the office, which interested me even less.
Making my way to the bar, I ordered a beer and chugged it down, hoping to get as happily drunk as possible, so this party would be tolerable. The dance floor was already crowded with people, and the noise level in the room was rising. I was taking it all in, trying to pretend that I was having a good time, when my eyes strayed to the door, and my jaw dropped open as a woman dressed in a Catwoman costume walked in.
I had never seen her before, I was sure of that. A blonde with a body like that was not something I was likely to forget. The upper part of her face was covered by a black plastic mask, complete with fake whiskers and cat’s ea
rs. The rest of her costume was also black: smooth black patent leather pants that clung to her so snugly they could’ve been painted on, a tight black leather corset that laced up the back and did amazing things for her tits, and spike-heeled black leather boots. A black leather whip hung from her waist.
My eyes swept her from her thigh-high boots to her stunning blond hair and back again, drinking in every movement she made, watching the way her pants pulled tightly over her body as she walked.
She sauntered over to the bar and ordered a drink, sipping it slowly as she looked around her. As her eyes finally fell on me, I saw her lips curl into a smile. I felt a bit embarrassed; I had been staring at her, and definitely not at her eyes. I was surprised and a little confused when she slid over to the stool next to me and sat down.
Still smiling at me, she reached out a hand and ran her long fingernails across my bare arm. I was totally taken aback by her forward behavior. I also couldn’t believe this stroke of good luck. She was beautiful, she was sexy, and all her attention was turned on me. Then, without saying a word, she grabbed my hand and pulled me onto the dance floor. She wrapped her arms around my neck and pressed herself to my body, grinding her hips against mine.
I pressed my hands against the small of her back and tried to settle into the steady rhythm of the music as she moved against me suggestively. She smelled incredible, of leather and shampoo, a hint of perfume, and some lotion. It was driving me crazy, and I was instantly aroused. When she moved in to kiss me I parted my lips and slid my tongue into her mouth, tasting her. I was so turned on I felt dizzy.
Letters to Penthouse XXXX Page 10