One day I was sitting alone in a popular coffeehouse, reading, when Annabel asked if she could sit at my table, since there were no free ones left. I vividly remember my first glance at her face. She looked gorgeous, very young and innocent, but friendly. She had big green eyes, black hair and small, even teeth. I later found out that she had been a part-time model.
Of course I said it was fine with me for her to sit there. She smiled and sat down, and we started to talk.
Annabel had a captivating habit of looking straight into my eyes as she chatted. I found out that she had just started at the honors college a month ago. Much to my surprise and delight, she seemed to value my opinion, and freely asked my advice about classes, extracurricular activities and so on. I managed to appear nonchalant when she talked happily about her boyfriend. Of course she has a boyfriend, I thought: She’s too beautiful and smart not to be taken.
Nevertheless, she did seem to be flirting with me a little, and as the afternoon went on she admitted that her boyfriend went to another school, and that they had agreed to see other people while they were apart.
When it was time to leave I offered to walk her back to her dorm, and she accepted. At the entrance to her building, she smiled and asked, “Can I call you sometime?” Of course I didn’t really think she ever would.
But within a week I heard her soft voice on my answering machine, and a few days later we had a wonderful, casual date. I couldn’t understand why she seemed impressed with me. She even seemed truly excited to ride in my sports car. (I had long ago resigned myself to the fact that guys usually expressed a hell of a lot more interest in that car than women did.)
I liked her too, but what primarily impressed me was her face and her compact, delicious body. I craved her. When she gave me one paltry good-night kiss, I grinned continually for days.
On our third date she wore tight black jeans and a little green sweater that accentuated her flat stomach by ending right above her navel. At the end of the evening I finally got her back to my room. She seemed a little nervous, which gave me confidence, although I was sure I was more nervous than she was. We started to kiss on my couch. At first, she just poked her tongue into my mouth in a tentative manner. She was definitely holding back a little, and I began to wonder if she was still a virgin. But in a little while she asked me if I wanted to give her a “massage.” She pulled off her sweater and quickly rolled onto her stomach.
I couldn’t believe my luck at the prospect of getting this pretty eighteen-year-old in the sack. There was no clasp on the back of her bra, so I just slid my hands beneath the thin green band as I caressed her shoulders and back. I could see the outline of her bikini underpants through her very tight jeans, and I attempted to slide my fingers beneath them. But the jeans were so tight my hand got stuck, and I had to take it out.
I was so horny now. I flipped her over and, without much pretense at massage, tackled the front clasp of the bra that obscured her cute little breasts. When I opened it, Annabel immediately sat up and climbed onto my knee. I leaned forward and kissed her nipple, then softly sucked on it. As it got hard, she let out a little sigh and started to rock back and forth on my leg. I went on sucking for all I was worth, and she got more and more aroused, grinding her crotch into my knee. I held her by the hips as she obviously enjoyed the friction and sucking. “Keep going,” she whispered. “Just like this.” So I continued to lick and suck and nibble on her breasts as she humped away, her eyes now closed. Soon she let out a few gasps, then whispered something unintelligible and moaned. Then she shuddered as she came in her jeans.
After a few moments, she smiled and, to my chagrin, said that she thought it was time to go. She had a test the next day and she had to study. Or something.
I realized that she was an incredible cocktease, but what could I do? I was just bedazzled by her, and let her dress and go without a word of protest or reproof. At least I’d gotten to second base.
I was frenziedly anxious to arrange another date, and when I did I vowed to go further. After all, I had learned to open a front-clasp bra on my first try. This time, however, I had still more stuff to learn.
We were back in my room, on my bed and slightly drunk. This time I pulled off Annabel’s shirt to find a Calvin Klein sports bra, with no clasp at all! I didn’t really know if I could easily yank it over her head, so I just lifted it over her tits, and concentrated on sucking them again. As before, she perched on my knee. I watched as she gyrated, gasped, murmured something and came.
Now was my chance. I wanted to show her just how much I wanted her. My hands went to her waist, and I undid the top button of her tight jeans while rolling her onto her back. Much to my chagrin, there were buttons all down the fly. I had never owned a pair of button-fly jeans, nor stripped them off any girl, so I didn’t realize that you could just pull down and free all the buttons at once. Instead, I fumbled at the first damn brass rivet.
After what seemed like an eternity, I managed to guide it through the buttonhole. As I forged ahead to the next metal button, my fingers brushed against the waistband of Annabel’s bikini panties. Annabel must have thought I was going so slowly in order to tease her, and she began to squirm with lust. “Hurry up!” she whispered urgently. “Make me come!” Well, sap that I was, instead of taking the opportunity to sweetly torture her a little, I immediately accommodated her by plunging my hand down between the partially opened denim jeans and her thin cotton briefs.
I really had to push a little to get my hand down to her crotch. Her panties were already very wet from her first orgasm, and I rubbed her pussy through them as well as I could in the constricted space. It was a little uncomfortable for me, but it seemed to be working out great for Annabel. The pleasure made her bounce around, but my trapped hand was securely in place and never lost contact with her vagina. She was thrashing and moaning with excitement. Soon she was convulsing again, and my fingers were moistened further by the increased wetness of her panties.
Now, as she relaxed and caught her breath, I had ample time to undo the rest of her fly and pull her jeans down her legs. It was then that she smiled shyly at me and said that she wasn’t ready to go all the way, and she wanted us to leave our underpants on.
Once again I complied with her wishes. In a frenzy of lust I went down on the beautiful freshman, vigorously licking and nibbling at her crotch through her panties. Occasionally, I would push the panties in and out of her slit. I concentrated on licking her clit through the thin material, until she shoved her crotch at my face and pounded her little fists against the bed as she treated herself to a third orgasm.
I so much wanted to fuck her now! But Annabel explained that she was still a virgin (though I wondered now how true that was). She told me that she had even prevented her boyfriend (I’d forgotten about that jackass!) from getting too carried away, by making sure they always left some clothes on. She also confided that his penis was so long that it sometimes poked over the top of his shorts. Well, that didn’t make me feel so great, especially since mine is about average; but it didn’t cool off my desire for her either.
She didn’t object when I started kissing and stroking her in an attempt to get her heated up again. It seemed to work, and this time as I caressed her vagina I managed to slip a finger under her panties and work it inside her. She seemed a little startled at first, but then her face became contorted with ecstasy. I couldn’t believe that this was a first for her, but she squirmed and panted with the joy of fucking my finger. More juices poured out of her, and a moment later she whispered: “Oh yes! I’m almost there!” She was shivering and tense, at the brink of climax.
At that moment I abruptly stopped, bringing a wail of disappointment from her. Taking advantage of her passion, I quickly got on top of her slender body and started to dry-hump her. Annabel went wild with lust and wrapped her legs around me. We mashed our underpants together. I concentrated on trying to rub my cock against her most sensitive spots. I felt her wetness seep through our briefs and
onto my penis. I couldn’t hold back any more after all these weeks of dreaming and fantasizing about Annabel, as well as fooling around with her. I cried out as I came, and I ejaculated all over her panties and her flat little stomach. As I did so, my young bed-mate pushed demonically up against my spewing cock, setting off her own climax. Because I’d kept her waiting, this orgasm, her fourth of the night, was her most intense. Annabel squealed loudly and rolled her head from side to side as she once again came in her panties.
The pretty freshman, now all tuckered out, fell asleep next to me. I was elated. Deep down, though, I probably realized that I could never keep a girl like that for very long.
Even so, it was a shock when I called her the next week to arrange a date and found her cold and distant. She brushed me off by telling me that she had an appointment with her teaching assistant. Well, good luck to him, the bastard!—G.V., Sacramento, California
BOTH SHE AND HER RECORDS WERE GOLDEN OLDIES, BUT THEY STILL MADE GREAT MUSIC
I’m a thirty-five-year-old man, and my girlfriend and I have been going together for three years. Rachel and I have always had a good sex life and to this day I have no complaints. Rachel is tall and sleek and has lots of long dark hair. She also has a very large, very close Jewish family that meets all the time for parties, holidays and just for the hell of it.
One of the key figures in this family is Rachel’s aunt Sybil. I often got paired with Sybil at holiday dinners, because we share an interest in old records, and we hit it off in spite of the vast difference in our ages. Sybil is in her early sixties, and is the antithesis of Rachel; she’s on the short side, and still has a fleshy kind of sexiness, with big breasts and powerful hips. She has dyed red hair, and she likes to show herself off in classic open-toed high heels and old-fashioned dresses that show off her bosom. Though she never married, she has a reputation in the family for having led a pretty wild life when she was young.
The last time the family got together for Passover, I was seated next to Sybil as usual, and we sat talking and laughing together for a long time after everybody else had moved to the other room. As we talked I couldn’t help being very aware of Sybil’s still highly attractive body. The dress she was wearing gave me a constant view down her capacious cleavage, where I could see the tops of her lacy bra cups, which just barely contained those great breasts. In addition, the hem of her dress had ridden up a bit, showing off a lot of stocking top, and her still firm and solid thighs. Hard as I tried not to stare, I couldn’t help myself, and I knew that Sybil was aware of it. To my surprise, all this flamboyant fleshiness, plus her closeness and the way she had of constantly touching the person she as speaking to, was getting me very turned on, and I had to make an attempt to hide the growing bulge in my trousers.
Sybil is too sharp not to notice such a thing. I saw her eyes flick over my crotch, just before she smiled at me knowingly and asked, “So how’s your sex life with Rachel these days?”
A little embarrassed, I replied that it was fine. “That’s good,” Sybil said, still smiling. “Life without good sex—” She shrugged. “What’s the point? But then, you’re a good-looking man, you know that. And I have always loved the company of a good-looking man. So listen, you want to come over some afternoon and listen to those old Patti Page records I’ve got?”
I couldn’t believe it. I was being openly propositioned by my girlfriend’s sixty-two-year-old aunt! I said I would like to very much.
Later on, feeling pangs of guilt, I mentioned to Rachel that Sybil and I had made a date to listen to some old records. Rachel couldn’t care less about old records. “Good,” she said. “Do it. She needs the entertainment.” Little did my sweet lady know just what she was approving.
So I went over to Sybil’s place one afternoon, and she opened the door to me in one of her great old dresses, which still fit her as though it had been poured on. She could have been a famous movie goddess, a bit on in years but still sexy as hell. She poured me a drink, put Patti Page on the turntable, sat herself down next to me on the couch, put her lips to mine and slid her tongue into my mouth. It was all over for me right there. I was hard in an instant, and now I found myself making out with a woman almost thirty years my senior.
Sybil was an expert at making out. She knew how to move against me as we kissed so that it drove me crazy, and within minutes I was running my hand inside her low-cut dress and feeling a long, hard nipple inside the bursting bra cup. She let out a little purr, and I can’t tell you how sexy it was to hear it, while my fingers kneaded that delicious nipple. The way her thighs worked against mine I could tell she was getting very turned on indeed.
I slid the top of her dress down then, and undid the front of her black lacy brassiere. A pair of the most beautiful breasts I’d ever seen dropped into view, and I sucked one large hardening nipple like a man possessed, while she writhed beneath me.
While I sucked her nipple I moved my hand down to the hem of her dress and slid it up the inside of her warm, full thigh. My fingers moved up, encountered the garter straps at the top of her stockings, and moved on to her hot, moist cunt. She was wearing garters but no panties. I gasped again as her hand adroitly undid my trousers and slid them down so that my cock popped up into view. Her fingers caressed it lightly. “Just beautiful,” she breathed into my ear. “Would you like me to suck it, darling?”
“God,” I said breathlessly. “Would I!”
And in a moment this sixty-year-old sexpot was kneeling between my thighs and giving me the blowjob of my life while I caressed those massive breasts. Sybil knew how to bring me right to the point of coming, then make me wait. When I thought I couldn’t take it any more, she said in a low voice, “So what do you say we fuck now?”
She led me into her bedroom, with its king-size bed, and I undressed her, piece by piece, unzipping her dress and letting it fall to the floor, dropping her slip and bra, till she was standing in her pearl necklace, her garter belt and stockings and high heels.
“What would you like?” she smiled.
“I want to lick you,” I said.
So Sybil sat on the edge of the bed and spread those beautiful thighs, and I dove between them and lapped up her delicious juices. Sybil wrapped her legs agilely around my head while I did that, locking her stockinged ankles behind it. Then she started to come, letting out deeper and deeper moans, her hips twisting and spasming convulsively.
“Fuck me now,” she whispered harshly. “Fuck me with that beautiful cock of yours.”
We slid together onto the bed like practiced lovers. She braced her high heels against the sheet and spread her stockinged thighs wide as I eased my cock into that fabulous, experienced cunt. Sybil had a gift that I’d never encountered in any other woman: her cunt could suck you like a full, thick-lipped mouth, while swallowing you down more easily than the most talented throat. But just as with her blowjobs, she knew when to slack off, and how to keep you going and going and going. Licking her lips, her eyes misting and her cheeks deeply flushed from her orgasms, she must have come a dozen times as I reamed her with powerful strokes. One of her hands was down between my legs, caressing my balls and my ass and the base of my cock as it moved in and out of her. I’d never felt anything like it in twenty years of fucking.
At one point she flipped herself over and had me give it to her from behind. After a few minutes of that she effortlessly rolled back. “Come now, come,” she breathed, drawing me down to her and enfolding me in her arms. I let out a yell as I plunged deep into that bottomless wet cunt and poured out an endless, hot river of come. Sybil cried out and convulsed beneath me, her suctioning cunt squeezing every last drop out of my spasming cock.
“Well,” Sybil panted, “wasn’t that a nice way to spend a pleasant afternoon?” If I’d had the strength to talk, I would have agreed with her.
Patti Page had long since sung herself out on the turntable when Sybil took my now limp dick into her mouth and got me hard again, and I shot a load of come down her eager thro
at. Later still, as she was letting me out at the door, she said, “Maybe we’ll do Theresa Brewer next time, yes, darling? It’s so nice to share the old music with you.”—Name and address withheld
IF THIS IS HOW WAITRESSES SERVE THEIR CUSTOMERS IN PORTUGAL, WE’RE ON OUR WAY
While on my way home from a long European business trip, I stopped for a few days in Lisbon, treating myself to a boutique hotel with a bar on the roof terrace, overlooking the ancient Portuguese city and harbor. On my first night at the bar I noticed the waitress right away. She seemed Portuguese, but not as conservative as most of the women of that country. She had long, very black hair pulled back in a bun, and dark mischievous eyes in her exotic face.
Because of my traveling and the cares of business, it had been two months since I’d had sex, and after a couple of drinks I was feeling ready for something more than cocktails.
The more I looked at the woman, the more inviting her glances became. When she brought over my last drink, I noticed she had turned the lights out and closed the door to the bar. I was the only customer left.
“You’re closing up—do I have to leave?” I asked.
She shook her head and put a sexy CD on the sound system, the music spilling into the warm night air.
I could hardly believe it when she walked over to me and started unbuttoning her oversize blouse. The high, full breasts that had been hidden under the big shirt now gleamed in the moonlight. I pushed my chair back as she reached me, and ran my hands under her long flowing skirt, my fingers exploring her long muscular legs. As I slid my hands upward, her skirt gathered around her waist, and the higher I reached, the more skin my fingers discovered. She wore nothing underneath—no underwear, no barrier to her tight round bottom.
She moved closer and swung her leg over mine. Nearly panting, I looked up at her, never releasing my gentle hold on her ass as it came into contact with my jeans and growing hard-on. When she straddled me her breasts landed right at mouth level. I took one rosy nipple into my mouth and suckled, pulling at it with my lips and twirling my tongue around the hardened bud.
Letters to Penthouse XIV Page 19