I’ve written before about the Christmas party when, with my husband out of town, I let a man 19 years younger than I come back to my room. Bert was modestly hung but very horny and turned out to be damn good in the sack.
That night Bert told me about his younger brother who was hung like a horse but couldn’t get laid when girls saw his erection! Bert asked if I’d let both of them come to my hotel room. With my husband out of town for several more days, I agreed to have dinner with them at six, saying we’d see where it went from there. Knowing myself, I was pretty sure I’d be getting it on with Bert again, and most likely with his brother too. Relieving a young man of his virginity is always a thrill.
I dressed to kill that evening, and don’t think it was my imagination that I turned more than one head when I stepped off the elevator. Near the door to the dining room I saw Bert and another handsome young man. Tremors of excitement rippled through me knowing they both were anticipating a piece of my ass and I was probably older than the two of them put together.
The first time I got my heart broken, I swore I wouldn’t let it happen again. It was just too painful. Maggie was the girl of my dreams. After she said I was the only guy she could ever see herself with, I found out she’d told four other guys the same thing. What a bitch!
When I met Ginny I was intrigued. She was the sweetest girl, with a heart as big as all outdoors. Not to mention that she was a very hot-looking chick—a natural blonde with gorgeous tits and hazel eyes that always seemed bright. We had a great deal in common, and she treated me like gold. The only problem was that Ginny was a virgin, and I would fuck anything with a pulse. No girl was off limits.
When we started dating we talked about sex. She was all for making out, and was happy to have oral sex. I could tell she was experienced in that area. She confirmed that she’d done that often, but no one had ever penetrated her vagina. Well, as long as I was with her, I would take what I could get, and I have to say I got it a lot. It seemed like Ginny couldn’t get enough of my cock in her mouth or my tongue in her pussy.
Every time I saw my dad’s friend Allen I got excited. He seemed like the man of my dreams—not only tall, slim and handsome, but also charming and funny.
The day after my high school graduation was my 18th birthday, so we had a double celebration. The morning after my big party Allen arrived at our house on leave from the Army. I woke up hearing his wonderful voice and laugh, but being tired and a bit hung over, I stayed in bed.
After a while I heard my bedroom door being eased open. I pretended to be asleep as Allen snuck up. Suddenly he yanked the covers off the bed, evidently unaware that I was naked underneath! We were both speechless for a long time. Then, slowly, he sat down on my bed and stared at my body. I couldn’t help noticing his excitement.
When I was young I had a best friend named Billy. We did everything together. We went to the same schools. We played the same sports. Even though I’m a girl, Billy treated me like one of the guys, and he would stick up for me when the other boys didn’t want me on their team because I was female. He was always fun to be around. We would play for hours and never be bored, because he was always thinking of something for us to do.
Summers were the best. We’d have picnics in my back yard, and play on the sliding board until it got too dark to see. I still miss those times when go back to them in my mind.
One winter day Billy didn’t show up at school. I thought maybe he was sick. But when I got home from school I saw a moving truck at Billy’s house. I ran over to see what was going on, and the man said the people who lived there had moved out. I was stunned, and ran home with tears running down my face. My mom confirmed what the man had told me. My friend was gone, and no one could tell me where he went.
My heart was broken. But life went on, and eventually, as children do, I got past the pain, fell into new routines and played with other friends. But I still thought of Billy, and continued to miss him in my mind.
I had always told myself I would leave this two-bit town, but I ended up having to go to a college close to home, as my mom got very sick and I needed to be there to take care of her. But I got a good education, and put it to use by getting a good job at our local library. I made decent pay and the work was challenging, so I was happy and content. I also started dating a man who I’d grown up with. Don was witty and kind, and while maybe not the most exciting man in the world, he had a good heart and treated me like a queen.
At 23 years old, I had never been with a man. I’d done some petting and dry-humping, but had never felt strongly enough about a man to let him fuck me. Don was handsome enough, but aside from copping a feel now and then he hadn’t made a serious move. He didn’t strike me as a prude, but I couldn’t help wondering why had hadn’t at least tried to get into my panties after six months of dating.
One day, as I was working at the library, I heard someone with a deep voice ask the girl at the front desk if I was around. I turned to look, and then just kind of froze, the books I was carrying dropping from my hands and falling to the floor with a loud bang. It was Billy! I couldn’t believe my eyes. I would have known him anywhere, and here he, was standing not 10 feet from me. I was stunned, and I started to tremble and cry. He moved toward me and opened his arms, and I somehow recovered myself enough to walk right into them.
He stroked my back as I wrapped my arms around him and just sobbed into his neck. He spoke to me soothingly and apologized for upsetting me, saying that if he’d known I would react like that he would have called first.
Feeling like a complete fool, with everybody looking at me as though I’d lost my mind, I pulled away from Billy and apologized to him and to everyone for disrupting things. I then took his hand and walked him back to my office, where we sat down and caught up on many things. He explained that he hadn’t known they were moving on that day so long ago, until he was in the car. His parents split up, and his mom took him down south to be with his grandmother. He had missed me terribly and had begged his mom to bring him back. But it wasn’t to be.
Billy had been married briefly, but it had ended badly, which was why he had felt compelled to come back to the only home he really knew, at least temporarily. His life now was in the south, but our town was where he felt at home—and where his best friend was. He went on to tell me how he had always thought of me and hoped to see me again some day. And here he was.
Billy was staying in a hotel in town, but I insisted he come stay with me in my home. I had a spare bedroom with a separate entrance, so he could come and go as he pleased without disturbing my ailing mother. After some persuasion, he agreed.
Things went amazingly well as Billy and I got to know each other again. It was as if we hadn’t missed a beat. The conversation just flowed, and I found myself really looking forward to our talks. I also realized I was developing other feelings for him, which terrified me, because he was leaving soon, and I didn’t want to go through the pain of losing him again.
One night about a week before he was to leave, Billy and I went out to dinner. We had some wine and promised each other that we wouldn’t lose touch again. He thanked me for being such a gracious hostess, and as he reached across the table to stroke my hand I felt as though electricity was coursing through my body. I felt all sorts of tingling sensations everywhere. We locked eyes, and at that moment we both just knew. We paid the check and almost ran back to my place.
We were barely in the door when we were locked in a passionate kiss. It was like nothing I had ever experienced before, and I wanted it to last. His hands were all over me, and it felt amazing. Slowly but surely my clothes were being stripped away from my body as the kiss continued. I felt amazingly sexy and naughty. I reached for his crotch and found a rather large bulge that literally pulsed in my hand as I stroked it. My God, it felt huge!
Somehow we made it to his bedroom. He pushed me gently back onto the bed and proceeded to take off his clothes. As he did so he told me how beautiful I was, and how sexy my body looked. I felt as if a raging fire was burning inside me, and I liked it!
Billy knelt on the bed, straddling my hips as he pulled me up to meet his lips. We kissed hard and deep, and it took my breath away. As he broke the kiss he worked his magic tongue down my neck. He nibbled my earlobes as his hands masterfully massaged my breasts, tweaking my nipples, evoking whimpers from me. He pushed me onto my back and ravaged me with his mouth. He seemed to be everywhere at once. My mind raced with desire, and my body responded with little jolts of pleasure.
The next thing I knew his hands were spreading my legs. I parted them willingly and waited for what I knew was about to come. Then I felt it—sheer pleasure! His tongue swiped at my wet folds like a thirsty dog at his water bowl. That tongue was all over my cunt. It was darting all around my clit, teasing it but not touching it. He sawed it in and out of my dripping hole, making my head swoon. His fingers were masterfully searching for my G-spot when, suddenly and quickly, he nipped at my clit. I saw the most amazing colors as my body convulsed in release. I could feel my stomach rippling with my orgasm. It was more than I could ever have hoped for, and I almost cried from the magic of it all. I grabbed at his head, my hips moving in a spasmodic dance of lust.
When he came up to mount me his face was covered in my juices. He kissed me as he entered me, and the feeling of his massive cock, along with the taste of my juices on his lips, made me come again instantly, all over his dick. He liked that. His pumping became almost manic as he looked down into my eyes. I was aroused to the point of no return as I looked back at my best friend and first lover. As his pace quickened and his breathing became more labored I begged him to fuck me harder. Spurred on by my request, Billy pushed himself deeper and deeper inside me, until finally I felt his whole body tense as his cock pulsed, shooting loads of come deep inside my body. And I came again. I had never dreamed that sex could be like this!
I never told Billy he was my first. I don’t know why; I just never did. After that night, he started thinking about staying, and the two of us sharing a life together. I, of course, thought that would be just perfect.
But when Billy went away for a day for a business meeting, I got very lonely, and horny. I couldn’t stop thinking about how great the sex had been, and I got so raunchy that I sought out Don (who I had ended things with), and seduced him. In fact, I fucked his brains out, and to my surprise I found out that the guy could really fuck! I only wished I had done this earlier, when he’d been so shy. We had amazing sex, and I found that I not only loved getting laid, I also loved variety!
When Billy came back, I told him that I didn’t think it would work out between us—at least not exclusively. He said he understood, and he still wanted to stay. So we’re still best friends, but now it’s with benefits.
—T. J., Jackson, Mississippi
Call me what you want, but there is nothing quite like taking a girl’s cherry in a bathroom stall!
I met Tabitha during our first year of college. She was a really hot piece of ass, which all my frat brothers tried to go after, but she told them in no uncertain terms to fuck off. So of course, in their eyes she was a bitch.
Tabitha and I had a couple of classes together, and I was struggling in both. She was an A student, so the professor in one of the classes asked her to help me. She wasn’t thrilled, but she gave me her schedule and told me when to meet her at the library. She also warned me that I’d better be serious and not waste her time.
I made it a point to be at the library on time. I was actually early, since I was boffing a sweet piece of ass there on a regular basis. It was nothing serious; we just hooked up in the men’s room (which I called my “office”) to fuck away the stresses of the day. There were a lot of stresses, and this girl—along with others, from time to time—relieved them, and I did the same for her.
As I approached the table where Tabitha had told me to meet her I saw that she was already there, scribbling notes on a pad in front of her. As I sat down beside her I told her that she could see I was serious, since I was there early. She raised her head, looked me dead in the eye and said, “From what I hear, you’re always here.” And went right back to writing her notes. So I guess my reputation preceded me.
When she was done with her notes we got right down to business. I have to say that she was a pretty good teacher, and I actually started getting it. We met that way for the next few weeks, and on the next exam I got a much better grade than usual. But the really big exam was only weeks away, and I needed to get at least a B, or be forced to take the class over again during the summer. I really did not want that to happen.
Tabitha was very patient with me, and a wonderful teacher, but I was really stressed out. My regular fuck partners were too busy studying for their exams to meet for any men’s room fun. I was quite frustrated and distracted, and Tabitha noticed. Finally she asked me what was wrong.
At first I told her that the work was just too hard, but she said she didn’t think that was what was bothering me. For a moment I wondered if I should just tell her that I was used to getting laid at least several times a week, and that I hadn’t had any pussy for seven days; but I didn’t think she would appreciate that, and I didn’t want to piss her off, so I just stuck with my story about the material being too difficult for me to get a handle on. At that point Tabitha threw her pencil down, stood up angrily and told me to get serious or get lost.
What the fuck did she want from me? I was trying, goddamnit! I couldn’t help the fact that my balls were fully loaded, but that my sperm had nowhere to go. Jerking off was all very well, but my cock needed some pussy—now! Her attitude had shriveled my dick at first, but now, seeing her standing over me, her hair in her face, her arms crossed under those amazing tits, it was all I could do not to take her right there on the table.
Suddenly, she took my hand and dragged me out of my chair. Her strength surprised me, but I followed her like a puppy, and was shocked and amazed when she led me into the men’s room and pushed me into a stall.
“Is this what you need to concentrate?” she demanded through gritted teeth as she pulled up her skirt and pulled off her sweater. Oh my God! She was gorgeous! If ever there was a perfect woman, Tabitha was it. Big tits, a small waist, long hair, strong legs, and a smooth-shaven twat! My head was spinning, but it didn’t impede my ability to strip my pants off.
“So that’s it,” Tabitha said breathlessly. “You need pussy to get your head on straight, do you?” And with that she came closer and kissed me, hard.
I think I really saw stars. I kissed her back, but after a moment she grabbed my face in her hands, saying, “Listen, mister. This virgin wants that giant hard cock in her slick, soaked cunt. Do you understand that? Can you comprehend that? I want you to do to me what you do to all the other girls you bring here to your ‘office!’”
“Yes . . . Yes,” I stammered out. Virgin? Really? Was that possible? But I wasn’t about to question my good luck. I grabbed her tits and started sucking on her erect nipples, while sliding my hand to her wet pussy. She wasn’t kidding when she said slick and soaked. This girl was dripping! I had to taste her. The confines of the stall made it difficult, but not impossible. I got down on my knees and spread her legs. Tabitha moaned and asked me what I was doing. Instead of answering I stuck my tongue up her hole and wiggled it around.
She grabbed my head to steady herself. “Oh my God, yeah!” she gasped out. “Oh fuck, that feels so fucking amazing! Oh my God, lick my pussy, baby. Oh fuck, yeah, lick it all over. Suck my clit, please. Oh please suck my clit for me!” Her words spurred me on, and I went to town, feasting on her virgin box. She moaned and grabbed my head harder, and when she came she tensed up and rolled her crotch all over my face.
Before she could even catch her breath I grabbed her by the hips and, sitting on the toilet bowl, had her straddle my lap. I slipped right into her slick sheath, and her warmth was out of this world. She started babbling again, talking like a girl who fucked for a living, and the more she talked the harder I got, until finally I told her I was going to come. She stayed with me all the way, and when I came she climaxed also. It was sensational.
I ended up failing the final exam, because my now devirginized teacher just couldn’t get enough dick, and ended up missing many scheduled study dates with me because she was busy fucking other guys. And when we did get together, we spent more time in the men’s room than at the books.
There was a silver lining though. Tabitha agreed to help me with the summer school program, and with just about everybody going home for the summer I knew I would have her to myself a lot more. I didn’t know how much studying I’d get in, but I knew I’d be getting in Tabitha all right, and that was worth giving up my summer vacation for. In fact, I figured it would make my summer vacation. And it did.
—T. K., Staten Island, New York
When I married Roger he was the only man I had ever been with sexually. I had done some light petting and kissing with some dates, but no boy ever got to grab or taste my goods. Soon word got around that I was a prude, and guys were told they shouldn’t waste their time even dating me. It got lonely in high school, I can tell you that, but I was brought up to believe that a woman’s virtue is the greatest gift she can give the man who becomes her husband. Yes, very “Leave it to Beaver,” I know, but that is what I was taught.
When I first met Roger we were counselors at a summer camp. He was from New York, and was the talk of the town. All the girls wanted to date him. I thought he was cute too, but I knew he had already been told to steer clear of me, the prude. He did date some of the girls I knew, but word soon got around that he was a player who left a trail of heartbroken girls behind him.
I thought his behavior was terrible, but I wasn’t crying for those girls either, since many of them were the ones who had called me a prude and warned guys not to ask me out.
To my surprise, as the camp was closing down at the end of the summer, Roger asked me if I would grab a bite with him sometime. When I just looked at him and laughed, he asked me what was so funny. I then told him that he had a reputation for using girls and then abandoning them, and it turned me off.
“Well, it beats being a prude!” he responded. “At least I’m having fun, and the ladies aren’t complaining either.” I could feel my face become flushed with fury, and I quickly turned and stormed off.
A few days later he and I accidentally ran into each other in the dining hall, and Roger apologized and asked me to please sit and have a soda with him. He made a sincere effort to explain himself to me, and after a three-hour conversation he had won me over, and actually had me swooning. Within a week we were dating exclusively. He had me over the moon, and he was loyal and true to me.
When he asked me to marry him, some of the girls tried to warn me about him, but I knew they were just jealous, nasty tramps who wished they were in my place. It felt good to be the one who was envied for a change. This prude had won a prize, and people recognized it!
On our wedding night, I was ready to give myself to Roger, but I was terrified. I had never let a man see me naked. I had never touched a penis, or had a man touch me anywhere explicit—except for the time I had allowed Roger to feel my tits through my sweater after he proposed to me. And now here I was naked in a hotel room with an experienced and equally naked man, with his cock standing straight out, inches from my mouth.
Roger taught me how to suck his dick that night. It was an awkward experience at first, but very exciting. I soon caught on, and from that night on I would suck him three or four times a day. I loved it!
When he went down on me and put his tongue on my clit, I exploded immediately. I had never felt such an exhilarating feeling before. My body shook and throbbed in places I didn’t know I had. Roger had to explain to me that I had had an orgasm. Wow! He made sure I had a bunch of them that night, and by the time it was over I was completely exhausted from the sheer pleasure we had given each other.
My introduction to sex had been more wonderful than I could have imagined, and I was very happy. I waited to give myself to my husband all the time. At first it bothered me, thinking about how many women he’d had before, and I wondered if I even came close to pleasing him the way they had. But Roger assured me that I was the best he’d ever had. He loved showing me what to do to please him, and he loved it even more when he no longer had to show me.
Now, 27 years later, this prude has really spread her wings—and legs. Roger and I have dabbled in swapping and wife-watching. He’s watched me with another woman, and has enjoyed directing me in a gang bang. We’ve taken racy pictures and made sexy videos that we love to watch over and over again.
Our life might not be very conventional, but I know that your audience will appreciate my story, and that’s why I wanted to share it with your magazine. Penthouse Letters has become our bible of sorts, and we can’t wait for it to show up every month. We just love it!
—Name and address withheld
It was in Baltimore, while I was overseeing an industrial show put on by my husband’s company, that I met Lou, a muscular masseur with whom I enjoyed two nights of steamy sex. During the second night he told me he thought I was just the one to deflower his brother Cal, who although he was 20 years old had never been with a woman. I was intrigued by this, and agreed to have sex with his brother that Friday night. Our show was closing that day, and on Saturday I would be supervising the loading of the equipment onto the trucks that would haul it back to the factory, before flying home on Sunday.
Once the show closed on Friday I hurried back to my hotel to prepare for my double date with Lou and his brother. I ordered up a light dinner, then douched and showered, wanting to be squeaky clean for Cal’s first experience. I dressed in lacy black lingerie with garters and hose, a tight skirt and a button-up blouse. I checked myself out and decided I looked pretty damn good for a 36-year-old woman who had been married for 18 years. It had been years since I’d taken on a virgin, and I wanted to give this young man a piece of ass he’d never forget.
I called my husband to check in with him, and told him I was dead tired and planned to go to bed early. He told me to rest my sweet little ass, because he was going to nail it to the mattress when I got home. I told him I couldn’t wait, and we hung up.
At seven o’clock I went down to the lounge where I was to meet the two guys. I spotted them as soon as I walked in, seated in a semi-circular booth. Lou stood to greet me warmly and introduce me to Cal, who stood up also to shake my hand; but I gave them each a big hug before sliding into the booth between them. I allowed my skirt to ride up, exposing the dark bands at the top of my hose, and just a hint of white flesh above them. This did not go unappreciated by either of them, but I pretended not to notice.
I found Cal to be just as courteous and likeable as his brother. We had a couple of drinks and just chatted for a while. Then, when Lou went to the restroom, I decided to break the ice.
“Your brother tells me you haven’t ever been to bed with a woman,” I said to Cal. “I find that hard to believe, after meeting you and talking to you.”
He looked embarrassed for a moment. Then he said, “Yes, it’s true. I’ve been close, but when a girl sees me with my pants off she panics, and tells me there’s no way I’m putting that inside them.” He shrugged. “But Lou told me he thought you were the woman who could help me out.”
Our table was secluded and in a dark corner, so I reached over and squeezed his package, saying, “I just love big cocks.”
Cal rapidly grew erect under my hand. He groaned softly. “Oh my God,” he panted. “I’m going to come in my pants if you keep squeezing me like that.”
I took my hand away, saying, “Okay, but why don’t you feel me up and see how wet my pussy is getting.” When he hesitated, I whispered, “Come on, Cal, there’ll only be a thin strip of wet silk between my pussy and your fingers, if you’ll just slip your hand up my skirt.”
He did so then, and he gasped when his fingers made contact with the slippery material covering my oozing crotch. His fingers traced the deep indentation of the clinging panties between my meaty cunt lips, which caused him to moan in my ear again, just as Lou returned. Cal pulled his hand back like a kid caught in the cookie jar, but not before Lou noticed what we were doing and winked at me. A few minutes later the three of us were heading up to my room.
Once there I kissed them both, then told Lou to sit down and watch while Cal and I had a little fun. I then led Cal to the bed and asked him to undress me.
His hands trembled as he began to unbutton my blouse. He opened it and removed it, then took off my bra. Sweat had broken out on his brow by the time he unzipped my skirt and slid it down and off, leaving me in just my garter belt, hose and very brief panties, which couldn’t completely contain my bushy red pubes. He stared at my crotch before reaching to pull my panties off, but I stopped him, saying, “Take off the hose and garter belt first.” He did so, and he was breathing as if he’d just run a marathon when he finally did get to remove the wispy panties.
I stood motionless as he knelt before me, looking at probably the first nude woman he had ever seen. I love it when a man admires my body, because I work hard to stay in shape. I’m just five feet two, weigh 106 pounds and measure 34C-22-32, and I’ve never met a man that didn’t like the way I look naked. Cal certainly seemed to like what he was looking at, and I widened my stance to reveal my puffy labia and the entrance to my vagina. He licked his lips and leaned forward to kiss those crimson lips briefly but eagerly.
I finally suggested that he might be more comfortable if he were naked too. At that point I was treated to a double strip show, for Lou stood up and removed his clothes at the same time Cal did, and I saw two enormous, amazing cocks standing tall and ready for me. I turned the bed down and lay down in the middle of it, raising my arms to Cal as I said, “Come here, sweetheart.”
He came and lay beside me, saying, “I don’t know what to do.”
I smiled at him. “Just hug and kiss me while you feel me up, to start with. Feel my pussy, Cal, and you’ll find it’s all wet and slick, because I’m horny as hell for you.”
His long fingers were shaking like vibrators as he pressed them between my legs. “My God,” he gasped. “It feels like hot melted butter down there!”
With that I raised and spread my legs, saying, “Fuck me, Cal. Fuck me right now.” He scrambled to mount me as I guided his throbbing cock straight to my entrance, and he slowly sank in me up to his balls. “Oh my God!” he said over and over, and he must have said it 20 times as he experienced the feeling of being inside a vagina for the first time.
He lay there, not moving a muscle, just marinating his meat for well over a minute before his instincts kicked in and he began to thrust gently in and out. He fucked me like that for another amazing minute before saying, “Oh shit, here it comes!” He again buried himself to the hilt as he pumped spurt after spurt of hot come into my cunt. But his cock remained hard as a rock, so when he’d caught his breath I urged him to fuck me again, and he was happy to comply.
After coming a second time he dismounted, and Lou climbed right on. He was so aroused from watching that he came quickly, but like Cal, he stayed in the saddle and fucked me to orgasm a few minutes later.
That was only the beginning of an unbelievable night of raw sex. They each fucked me three more times before we went to sleep, and I was awakened several times during the night when one or the other crawled on to get a little nookie.
I fucked them again the next morning before I left to for the exhibit hall. When I got there I learned that our field foreman had fired his helper for showing up drunk. Knowing that Cal was unemployed, I called him to ask if he wanted to earn a few bucks by helping out. He jumped at the chance, and by the time the trucks were loaded the foreman had asked me if we could hire him to replace the guy he’d fired. Cal was overjoyed, and was more than ready to make the move, since he had been out of work for some time.
I told Cal he would have to be very careful not to do anything that would cause my husband to get suspicious. After all, he was going to be working for the man who was married to the woman he was screwing.
Cal worked for our company for five years, making good money and enjoying good benefits—including getting to fuck me several times a week.
—R.M., Miami, Florida
My husband popped my cherry. This doesn’t sound very risky or adventurous, but it was both. It happened Saturday night, January 18, 1969. Back then “nice” girls were supposed to be virgins till they were married, and unmarried girls including me weren’t given the Pill.
The risk and adventure came because Al wasn’t yet my husband. He’d just officially become my fianc . And there I was, lying on my back in his bed, naked save for my engagement ring and diamond-studded earrings, with his hard, dangerously bareback cock thrusting in and out of my till-two-minutes-ago-virgin pussy.
I’d met Al a year and a half before, when I was 19 and a bridesmaid in a wedding he also attended. He was 28. The first date was pretty innocent, but we moved on to parking and making out. Soon we were going to his apartment. The first time, when we were rolling around, my dress got pretty wrinkled. We decided if I took it off but left my slip and lingerie on, that would be okay. Of course, as time went on, more clothes came off. Soon I was in his bed naked from the waist up with only my panties on, but I told him they were to stay on and he was to keep out of them.
It was just after my sophomore year in college. Fresh man year one of my sorority sisters and her boyfriend had made a baby in the back seat of his car. We sisters didn’t know whether it was a pure accident condom mishap or baby roulette the guy trying to pull out just before he shot, or, more dangerously, shooting his seed in her pussy and just hoping for good luck . Whichever it was, they had a pregnancy on their hands they didn’t want. We sisters concluded that the only sure way to prevent that back then was to stay a virgin. We weren’t opposed to above-the-waist fondling and sucking, but below-the-waist was off limits.
Al took off his clothes to avoid wrinkling them and put on tennis shorts. He was careful not to let me see his penis, but while we rolled around, I felt it nice and hard through the tennis shorts. It felt good, but each time he would stop after a while and kind of sigh. I soon learned that we were dry-humping till he shot his load in the shorts. He said later that he had left enough come in them to populate a good-size nursery school.
Anyway, after the formal engagement dinner, we had all gone back to Al’s apartment. Finally everyone else left. My parents drove to their home in a smaller town about 50 miles away, but I was staying with the couple at whose wedding I’d been a bridesmaid. As soon as we were alone, we shed our clothes in record time. In my haste I took off not only my pantyhose but also my pant ies, but Al had his tennis shorts on. Soon his hands and mouth were all over my bare tits, and we started to do a little humping.
It was dark, but he soon realized that I was naked and he began to feel around the tops of my legs and brush his hands through my pubic hair. Soon he was rubbing my pussy lips, then my clit, and then he was ten tatively putting a finger in me. He moved slowly at first, but when I responded by moving my hips, he went faster. I was getting wet. He pulled his finger out, and I felt something bigger at the opening of my pussy. It was slowly pushing its way in. I moved against it the way I had pushed against his finger. He pushed some more. I pushed some more.
Now I wasn’t a virgin, but I still had my cherry. A couple of more pushes took out my cherry. Soon we were fornicating vigorously. Losing my cherry hadn’t hurt—it just felt a little weird. But get ting laid for the first time with what felt like a really large cock, after so much foreplay and being so wet, felt absolutely great. I wasn’t thinking at all about birth control or getting pregnant, just enjoying my first fuck.
Al wasn’t inexperienced, and suddenly he pulled out. I felt some warm sticky goo on my tummy just above my pussy hair. He got up and told me to lie really still. He went in the bathroom and came back with a damp washcloth, and carefully cleaned off my tummy so his semen wouldn’t crawl its way down to my pussy.
When I got up to go to the bathroom, I discovered that I had blood coming out of my pussy and running down my legs. Al helped me clean that up. Luckily, it was about time for my peri od, so I had the necessary feminine items with me to take care of the bleeding. We discovered that blood had run down my legs and perfectly outlined where I had been lying when I lost my cherry. Al threw away the sheets, but the outline had gone through to the mattress. So for the first few years of our married life we had a vivid reminder of our first time.
The next day Al took his deflowered fianc e back to my unsuspecting parents’ house. I went back to college, but was able to return home—and to Al’s bed—the next weekend. Since there was no question that we both were eager to fuck again, he got a rubber out of his bedside table and put” it on. But for our nerves’ sake it would have been better if he’d fucked me bareback and pulled out. I’ll explain.
After Al came, we lay there hugging for a long enough time that when he pulled his penis out, the rubber stayed in me. While he was frantically searching all over the bed for it, I went in the bathroom, and when I” came out told him where it had been. I pulled it out and threw it in the toilet. But we were both horrified.
I went back to college. Naturally, my period was late—so late that I had to confide in my roommates. One of them asked her older sister-in-law to help get an appointment with a doctor so I could find out. Luckily, before the appointment my period came.
I wasn’t able to leave college or have Al visit till spring vacation because of a very difficult course that required a lengthy paper. Even though we’d had quite a scare, we were eager to keep fornicating. And having my room mates know that I was sleeping with Al had its uses. I was able to leave for vacation Thurs day evening instead of Fri day as I’d told my parents. To keep them from finding out, my roommates agreed that if the parents phoned, they would say that I was out and that they would tell me to call home when I got back, and then the roommates would call Al’s apartment and I could call my parents from there. As it turned out, my parents didn’t call.
I flew to the airport in Al’s town. Luckily, no one who knew me saw us. We went directly to Al’s apartment. I” had bought a short nightgown that barely covered my bush, but that didn’t matter because it was so sheer that Al could see not only my bush but my nipples as well. Anyhow, it didn’t stay on very long.
When we got ready to fuck, Al reached for the drawer where he kept his rubbers, but I told him no, I didn’t want a repeat of what happened our second time. He said later he could have explained that he realized what he had done wrong but he was so eager to fuck me that he went ahead bare back. That night we did it at” least three times. He told me later that between times he was careful to pee and wash off his cock with soap and water.
The next day Al took a well-fucked daughter to my parents’ house as if I had arrived on a Friday plane.
Al’s town’s public library was a lot bigger than the one in my hometown, so I used the excuse of studying in that library which I actually did to spend time there. I spent several nights with the recently married couple. Of course, I would spend a few hours in Al’s bed before he took me to their house. We got accustomed to making love on a regular basis.
One morning during spring break I was having my bridal picture taken at a photographer’s in Al’s town, so I stayed with the married couple the night before. When we got to Al’s apartment, I had to tell him that I” was both glad and sorry to” tell him that my period had started. He said that if I didn’t mind, he didn’t mind, since I” had bled all over his penis the night he relieved me of my virginity.
This time Al got out a towel to protect the sheets. We really went at it, and he came inside my pussy for the first time bareback. We figured that was a pretty low-risk form of baby roulette. The next day, the virginal-looking bride-to-be had her picture taken in a lovely white wedding dress with probably a good part of her fianc -lover’s load in her pussy.
I was to return to college on a Saturday morning plane from the small airport in my hometown, so my parents invited Al to spend the night—in their guest room, of course! We didn’t have much chance for anything but a few kisses before we went to bed. In the morning, my father, having his own business and being an early riser, was out of the house by eight, and since my mother and teenage brother were late sleepers, and the house was pretty large . . . eager for one last fuck before I left for college, I sneaked in the guest room.
When Al saw me, he got a big lustful grin. I pulled off” my pajama bottom, he shed his boxers, and in no time his cock was thrusting in and out of me. We had to hurry and have him get his rocks off so we wouldn’t get caught. The danger of being caught and the back-of-the-mind knowledge that we were playing baby roulette for real added to the thrill.
Al cleaned his come off my tummy with his handkerchief. As far as I knew we weren’t found out, but when my mother asked Al if he’d had a good night, he turned a bit red and almost choked on his breakfast.
On the way to the airport, I suggested to Al that we should elope to a nearby state that specialized in quickie marriages. I said my mother was complaining so much about all the details of the wedding that I thought we should just do it. But maybe subconsciously I was worried about losing at baby roulette. So we drove to Al’s apartment to call to see about the quickie marriage, but they didn’t do it on weekends.
We decided that Al would have to drive me back to col lege that day. But with his bed available, we played another game of baby roulette maybe three hours after our first one of the morning.
Luckily, none of my roommates had returned to our apartment, so Al stayed in my bed and fucked me at least three times—always a” bareback baby-roulette fuck. He left the next day, and to this day we don’t think anyone knew but us, except perhaps the guys in” the apartment next door we were so vigorous that the bed made a lot of noise. It wasn’t until months later that we realized we’d fucked in three different cities in less than 24 hours!
I didn’t see Al till the night before my graduation. By then my mother had given me the Pill to start taking in anticipation of my marriage and I’m sure, in her mind, in anticipation of my “first intercourse” . When Al got to my apartment my parents were there, so he asked if there was “someplace we could go.” I knew what he meant!
We were able to get away to a public park. We started making out, and he got some bare tit and panty-covered pussy. Since he had a small sports car, too confined for fucking, he’d brought a blan ket, and we went to a dark part of the park. I had a skirt on, so he helped me pull off my panties and pushed his pants and boxers down. This time we didn’t intend for him to pull out. I was at last on the Pill, and we had to start trusting it sometime! Be sides, it was so close to the wedding that the worst we might have was an “eight-month pregnancy.”
We did encounter one small problem: Just after Al shot his load in my pussy, cops appeared and arrest ed us! He spent the night in jail. But the dean of students didn’t want a scandal and persuaded the cops and judge to change the charge to “disturbing the peace by means of improper attire” from “indecent behavior,” or in plain language fucking in public. Al paid a small fine for both of us. Luckily, my parents never found out.
It was only a month to the wedding. We got in lots of sex. I often had a pussy full of Al’s jism when we went to parties in our honor. One of the best was on his 30th birthday. After a family lunch we went to his apartment. Once we were naked and he had played around with my tits and fingered my pussy, he lay down on his back and invited me to hop on his straight-up cock.
I did so, and rode him cowgirl, and I kept riding after he shot his load in my pussy. His comehole was so tender, he said it was an exquisite mixture of pleasure and pain. Afterward, I had to be careful to check out my panties and be ab solutely sure that none of Al’s come had dripped into them for my mother to see when she did the laundry.
So on my wedding day my wonderful but na ve father thought he was giving away a virgin daughter to her groom to have in bed for the first time. In reality I” was already a lascivious mistress to my groom, a shameless lover of fucking who had had a pregnancy scare and been arrested for public fornication. But I had lustfully played the game of” baby roulette and won.—Name and address withheld
After losing my husband in a horrible accident, I found no lack of friends wanting to console me, especially the men. I was never so down in my life, and was drinking way too much, which made me an easy conquest. For the first few months it wasn’t unusual for me to have three or four men in my bed in a 24-hour period.
One morning I woke up with a man I didn’t recognize! I remembered my friend Lonny stopping over the night before but couldn’t remember going to bed with him or the man who now lay beside me. I slipped out of bed without disturbing him and locked myself in the bathroom, where I discovered that I’d undoubtedly had sex that night.
I showered and dressed, thankful that my dressing room adjoined the bathroom. Dressed in jeans and a sweatshirt that covered me well, I went back in the bedroom and woke the guy and asked him to leave. While he dressed, I leaned against the dresser watching, and noted that he had a really good-size cock. Had I really become such a zombie that I couldn’t remember being screwed by that? This had to change, and now.
I decided I had to get away, make a fresh start where people didn’t know me. I had money in the bank and nothing holding me there. I thought of San Diego, where my old friend Connie works in real estate, and booked the next available flight, the following morning. Then I made lists of things to pack and things to do before leaving.
I called Connie and told her I wanted to lease a furnished condo for several months. She said she had just what I needed, available immediately. I arranged to have most of my things shipped when I had an address, and arranged with my friend Grace to care for my house. And the next evening I was 1500 miles from the place where I’d let my life go so wrong.
Connie had arranged it so all I had to do was sign the papers and move into a comfortable one-bedroom unit on the second floor over looking a nice pool. With the manager’s help, Connie had gone the extra mile—put ting linens on the bed and towels in the bathroom and having the utilities turned on. So I ordered a pizza and while I waited unpacked my bags. After eating, I fell in bed and slept for 13 hours.
After showering, I went out and bought a car, then went grocery shopping and back to my new home. In my new routine, I kept to myself, often taking day-long drives into the countryside to sightsee and eat in out-of-the-way places, where I met the nicest people.
I’d been there nine weeks when I awoke in the middle of the night from an erotic dream and had an intense desire to masturbate, for the first time since I arrived. I’ve always been an avid masturbator, having been taught that it’s natural to desire to pleasure oneself. I sleep in the nude, so it was easy to begin caressing my large breasts and tweaking my sensitive nipples. Want ing to prolong the sweet agony of my desire, I traced my fingertips slowly down over my tummy, then bypassed my curly bush and teased the tender flesh of my inner thighs within an inch of my pussy, which by then was emitting the musky aroma of a woman in heat.
Unable to keep my fingers away any longer, I traced the length of my buttered pussy lips, stopping short of touching my swollen clit. I cupped my vulva, applying just enough pressure to my throbbing clit to send the first tremors of release through my body. I rubbed my cunt gently but steadily. White-hot flashes of orgasmic pleasure shot through me.
When the room stopped spinning, I had a burning desire to have my pussy stuffed with cock. I reached in the nightstand for a large pink dildo I’d brought along, which I hadn’t used in years, then raised and spread my legs and slid eight inches of” cold rubber cock in my cunt. I fucked myself for nearly an hour, until I was too weak to continue, then placed a pillow between my thighs and fell asleep with my rubber lover embedded in my soupy snatch. When I awoke in the morning it was lying beside me like any other lover.
A few days later I ran into Marty, a polite young man who lived in the complex and always greeted me with a smile. I had just set down a large box I was trying to get upstairs containing things Grace had shipped me from home. Marty lifted the box and carried it to my door. I thanked him and said I could handle it from there, and he said I could thank him by go ing to dinner with him Fri day night. I surprised my self by accepting the invitation.
I had a lovely time. After ward he saw me safely inside my door, then thanked me for going out with him, bid me good night and, after I thanked him, left.
Marty and I became an unofficial couple, doing many things together in the next six weeks, but never going beyond a kiss on the cheek. Then we progressed to lip-to-lip kisses.
He persuaded me to go to a party a friend of his was having one Saturday night, and we had a great time. But since I hadn’t been drinking more than the occasional glass of wine with dinner, the drinks I’d had kicked my ass. In the cab home I was giggling and acting like a school girl. And then we were locked in a heated embrace, kissing passionately.
Even while we continued kissing, swapping tongues like lovers, Marty’s hands never left my shoulders. I didn’t want it to end! I only worried that he was too shy to make further advances. I dropped my hand to his leg and slid it up to his crotch, where I discovered a nice hard cock that reached to his belt and felt very thick. I” traced its outline several times, until he groaned and came in his pants, soaking a six-inch area.
He was terribly embarrassed, but I told him I took it as the greatest compliment I’d ever received that a man so much younger than me was that aroused by my touch. I unzipped him and while kissing him fished out his semen-covered half-hard cock. When our lips parted, I lowered my head to his lap and took his entire cockhead in my mouth.
He had an odd-shaped glans, but it was too dark to see, so I just licked his salty come off it. Instantly he be came fully erect. I sucked as much of his erection as I could, but it was so thick that I couldn’t take in more than the head and an inch or so of shaft. It throbbed, and soon a dozen large spurts of come shot down my throat.
I tucked his cock back in his pants and zipped him up just moments before the cab pulled in front of my condo. I didn’t even try to keep my dress down as I got out, giving my young friend a good look at my lacy black garters and panties.
I was taken by surprise when I opened my door and Marty merely gave me a quick kiss and said, “Thank you for going out with me. I really enjoyed it.”
I recovered quick enough to wrap my arms around him and lay a sizzling kiss on him. I pressed my body to him, creating a column of hard cock in his pants. He said nothing as I” led him in and closed the door.
We stood inside the door locked in a heated embrace for several minutes. Marty slid his hands down and cupped my ass cheeks and squeezed them gently. I felt the hot wetness of desire between my legs and for the first time since the accident really wanted a man to make love to me, not just use me for a hot fuck.
I whispered, “Come in my bedroom, Marty. I want you to make love to me.”
Again I took his hand, and led him to the bedroom. I un buttoned his shirt and undid his pants and helped him out of his shoes and pants, then asked him to unzip my dress. I stepped out of it and turned to face him in my lacy black lingerie. His eyes were bugging out of his head! I gave him a reassuring kiss, this time pressing my soft lace-covered breasts against his bare chest while I stroked his erection, inspiring him to unhook my bra clasp.
I stepped back enough to let the bra drop between us and give Marty a view of my tits with the large pink nipples standing as erect as his rampant penis. I hugged him, with only his still-damp shorts and my brief panties separating our bodies.
I turned the bed covers down and pulled him down on the bed with me. After we shared several fevered kisses, I sat up and tugged his shorts off and got my first look at his cock. It was about average in length, but ” the glans was unusually shaped, as I’d gathered—enough wider than the shaft to explain why I couldn’t throat him. His pubic hair was matted with semen, which only made me want his cock worse.
I licked his balls and started up the shaft, but he pulled me up, saying, “Don’t do that. It’ll go off again.”
I lay back on the bed and asked him to take my panties off, which he did, then stared for nearly a minute.
I said, “Take me, Marty.”
He said, “Oh damn, Kim, you’re going to find out anyway. I’m a dumb virgin.”
I pulled him into my arms and said, “Honey, you’re not dumb, just inexperienced. I promise you’ll never forget tonight. Just get on top of me between my legs. Oh yes! Doesn’t that make you feel close to me?”
I heard a whispered yes, then guided his erection to my wet snatch and pulled his hips down. His odd-shaped cockhead entered me, and then gradually his whole cock. I wasn’t surprised to feel it throb and after only three awkward thrusts release a deluge. He ” collapsed on top of me,” and I held him until he recovered enough to give me a tender kiss and a whispered “thank you” as he began to pull out.
I wrapped my legs around him and said, “I’m not letting you get away so fast. Fuck me all night, Marty.”
He fucked me in the” good old missionary position again, where he found a rhythm and learned not to withdraw too far on the outstroke. This time he brought me to climax after about three minutes. After he shot his load, his erection faded and slipped out. We lay hold ing one another. He seemed to be in deep thought. I took his spent cock in my hand and stroked it lovingly. Slowly he became erect again.
I strad dled him and slid his erection in me, then rode him slowly. A look of amaze ment came over his face. He moved his hands slowly up my torso and cupped my soft mounds. I rode him for about 20 minutes, pausing every time I felt he was nearing orgasm to let his passion subside. When I began rubbing my aching clit, his eyes dropped to my groin. I took him to the promised land, milking his cock with my clenching cunt, then rolled off and laid with my ass snuggled up against his soft cock and his hand clutching my breast. I was content to fall asleep, but soon felt his cock getting hard again. I raised my leg and reached between my legs to guide him in from the rear, then gave him one more long slow piece of ass before we fell asleep.
When I awoke, I found Marty already awake, watch ing me with a big smile. My hand was wrapped around his morning wood! I kissed him and said, “Give me a minute to go the bathroom and we’ll put this beauty where it belongs.” When I came back, we had a long, beautiful fuck, and then in the shower he fucked me again, pressed up against the cool tile.
I went to fix breakfast, and after eating we sat at the table drinking coffee and talking about our lives. I” took his hand in mine be fore I asked why he had remained a virgin. He said he never knew his father, who left town after getting his mother pregnant, and she always preached the evils of sex, using herself as” an example of how God punished those who have sex without marriage.
I told him I didn’t know how long I was going to be in San Diego, but I would be happy to be his woman as long as I was, and give him lessons in love and in self”‘confidence. We walked hand in hand back to the bedroom, where we spent the rest of the day.
I stayed in San Diego another seven months and had an incredible sexual relationship with Marty, teaching him everything I” know about the physical pleasures that a man and woman can share. While he was finding the self-confidence he needed, I found my peace. Although many years have passed, I have never forgotten Marty.—K.B., Tacoma, Washington
Everybody remembers their first fuck. I know I sure do. It was just two weeks past my 18th birthday, and I was help ing my grandparents doing odd jobs like mowing the yard and garden work. I got to chatting with Maureen, the next-door neighbor, a woman in her early 50s, and being a horny teen I could not help but stare at her sizable tits. I told her if she needed any jobs to be done I’d be willing to put my tools to good use.
The next day Maureen told me her stereo system needed reprogramming and asked if I could come over. Again my attention was regularly diverted to her tits. She ushered me to her living room and bent over, and I got a flash of the curve of her lower butt. I told her that before programming I want ed to check all the wiring, thinking that this would give me a chance to look up her dress. She went to the kitch en to get me a drink, then returned and stood over me, and I was right, I could see up her dress—way up her thigh to near her crotch.
She caught me, and after noticing my bulge said, “I see I’m going to have to keep an eye on you. You’re trying to look up my skirt.”
I didn’t know what to say. Fortunately she knew what to do. She lifted her skirt to reveal her dark pantyhose with white panties beneath. “Is this what you want to see, you pervert?” she said. My cock was hard, but I was still very nervous. Was she going to tell on me? Was she going to kick me?
As I debated possibilities in my head, Maureen said, “Come on then, we’re going upstairs,” and reached her hand down to pull me up.
What the hell, I thought. She might be old enough to be my grandmother, but she was hot, and a fuck’s a fuck, especially for my first. So she led me upstairs, then un dressed me, and I watched with a throbbing hard-on as she took off her skirt and pantyhose. She told me not to touch my cock so that I wouldn’t come too soon. She came to me and unclipped her bra, inches from my face, and her big tits burst free and hit me.
“Suck them now,” she said, and I did, eagerly. I sucked her extremely hard nipples, and judging from her moans and groans, I was doing an okay job.
Finally, I slid a hand up her inner thigh to her panty crotch. I rubbed her through the fabric, then tugged at her panties until I got a look at my first cunt, hairy and wet. I slipped two fingers in, and she gasped and whimpered while I fingered her. She shivered and said to fuck her.
Maureen knelt on the edge of the bed and put her hand between her legs to show me where to put my cock. “Here,” she said, and I got behind her and pushed my cock in. She was hot and wet, maybe a little loose, but I had nothing to compare it with, so it felt sensational.
I knew I wasn’t going to last long before I came, and Maureen sensed it and said, “Don’t you dare come in me yet. Pull out and use your tongue.” Obviously that was a first for me too, and I did my best to please her. She tasted musky, but good enough to continue. I gave her a climax, and then want ed more of my cock in her pussy. When I said I wanted to fuck her more, she laid on her back and spread her thighs, and I climbed on.
As I pushed my cock back in her, I said, “Now I’m going to fuck you hard,” and I did. The bed kept hitting the wall, and her moans and groans filled the room until she cried that she was coming, a second before I shot my load in her.
When I pulled out, I marveled at my come leaking out of Maureen’s hole. She lay panting, then pulled me to her and licked my cock clean of both our juices. She licked and sucked till I was ready to mount her again. I lasted much longer this time than the first. I wore her out that day and a number of other days that summer.
I’m still turned on thinking of her, and still frequently jerk off to the memory of her. —N.A., Kitchener, Ontario