tagLetters & TranscriptsDiary of an Oversexed Woman

Diary of an Oversexed Woman


I'm a vibrant forty-something year old divorcee who has an active sex life. I've been blessed with a petite figure and a pretty face, so I've never had problems finding willing partners to help me explore my sexuality. I love sex, and I especially love giving blowjobs. I love everything about sucking cock, the look of ecstasy in my partner's eyes, the feeling of a hard cock throbbing in my mouth, and of course the taste and texture of my lover's cum. I get excited just thinking about it. I can give head for hours and I never tire or get bored. In fact I've made an evening of giving head on several occasions, much to my partner's delights.

I've always been open-minded sexually and love to experiment. I'll try almost anything once within reason and as long as it doesn't hurt. I've had sex in all kinds of places like, cars, boats, beaches, elevators, and restrooms, and I've slept with a variety of lovers of various ethnicity; I love variety. I'm also one of those lucky women who are multi-orgasmic and usually come several times in a night. Thankfully I've been with lots of skillful lovers.

I've kept a diary of some of my hottest encounters. I read them from time to time and have even shared them with lovers over the years and I got to thinking how hot it would be to share them with our readers. So enjoy them. I hope they turn you on as much as they do me.

Saturday, May 2nd, 1983 -- My First BJ

Date night, a 1981 Impala, and my high school boyfriend. I was 19 and credit Matt for introducing me to the wonderful world of oral sex. We were making out in the car when Matt unbuckled his jeans and lowered my head over his cock. I took him into my mouth and bobbed my head up and down, which seemed like the natural thing to do. Well, it didn't take Matt long to come, and he came in my mouth. Not knowing what to do, I simply swallowed it. It tasted ok and I remember getting pretty turned on by the experience. After I swallowed, I just kept on sucking him and playing with his balls. To my delight Matt came again, and again I swallowed. Once I got a taste of sucking I was hooked. After that night I blew him every chance I got, which was often. Yum!

Friday, April 19th, 1991 -- Menage a Trois

My first threesome was completely unexpected. It was with my friend Jeanine and her boyfriend, Bill. Jeanine and I roomed together in college a year earlier. She was a bit on the wild side and adventurous and bedded several guys, experimenting with anal sex, group sex, and even with other girls, which she said was great. Jeanine used stuff like blindfolds, cuffs, and vibrators, things that I never even thought about using.

Anyway, one night we were out at a local pub and Jeanine was horny, checking out different guys and making comments about the good looking ones. No one tickled her fancy so after a few drinks she decided we'd pop in on Bill. My plan was to walk home from Bill's place once we got there so Jeanine and Bill could be alone, but that's not exactly how the evening went.

We arrived at Bill's apartment to find him hanging out watching TV. He let us in, poured us some wine and lit a joint. We joined him the couch, drinking and smoking when after a short while I left the room to use the restroom. I was gone only for a few minutes but when I returned Jeanine was on her knees with her head between Bill's legs and his cock in her mouth. I stopped dead in my tracks, trying to process what I was seeing. Jeanine lifted her head, turned around and motioned for me to come toward her. I walked over to the couch and sat next to Bill.

The next few moments are still a blur. Bill immediately pulled me close and kissed me. As his tongue darted in and out of my mouth he began caressing my breasts through my sweater. I was turned on and kept my eyes on Jeanine, watching her engulf Bill while we continued kissing.

Jeanine lifted her head and suggested we move to Bill's bedroom. Bill turned off the TV, removed his pants and underwear from his ankles, and let the way to the bedroom. Once in the bedroom Bill removed his shirt and unbuttoned my jeans while Jeanine removed her clothes. Once my jeans hit the floor and I stepped out of them, Bill helped me remove my sweater and bra. I stood fully naked as Bill and Jeanine lay on the bed. I lay next to Bill and watched Jeanine slowly kiss his torso. Soon Jeanine was sucking him again and Bill began kissing me. We made out for a while before he gently pushed my head downward toward Jeanine; I knew what he wanted and was all too eager to oblige.

I kissed his chest and stomach before positioning myself across from Jeanine. I had never been this close to a naked woman before and was a little nervous, but that didn't stop me. I licked the bottom of Bill's shaft while Jeanine kept sucking him. I became more brazen and licked his shaft up and down while Jeanine wrapped her lips around his head, occasionally twirling her tongue around in circular motions. Jeanine removed her lips from Bill head and began licking the other side of his shaft. At one point the tips of our tongues touched and I remember thinking how sexy that was. Apparently Bill thought so too because I heard him say that he was coming and moments later I felt a warm splash of semen hit my lips, followed by another and then another. Cum dribbled down his shaft and Jeanine and I lapped it all up.

We screwed around most of the night in various positions and I think Bill came a half dozen times before we were through with him. Jeanine and I didn't do anything with each other however, instead focusing only on Bill. Still, it was a hot night.

Wednesday, January 12th, 1994 -- An Older Man

When I was in my late twenties I realized that guys my age were interested in one thing, getting themselves off. They were selfish and had little desire to please; they wanted pleasure, not the other way around. I grew tired of that and wanted a less selfish lover. A couple of my friends admitted to bedding older, more mature men, and they all said that it was the best sex they ever had. In fact, one friend said that it was unlikely that she'd have sex with any man under the age of forty. That was saying a lot coming from a twenty-seven year old. I was intrigued, to say the least. I was young and attractive and never had a problem attracting men in the past, so I had no reason to believe that have any trouble hooking up with an older man; I just had to find the right guy. I knew that finding the right guy would be a challenge since most older men were married, but, I that didn't stop me from trying. A few months later, that day arrived.

I met John while on a business trip on a cold, snowy Minneapolis winter's evening. I stopped at the hotel's lounge for a drink to warm me up and John immediately caught my eye. He looked to be in his mid to late forties, maybe fifty tops. He was attractive; tall and thin with a mustache and goatee that matched his salt and pepper hair. I pulled up a chair next to him, ordered my Knob Creek, neat, and introduced myself.

John and I talked for a couple of hours and I learned a little about him and his business. After my third bourbon my inhibitions began to wane and I began to flirt with him. I held my stares just long enough to make him slightly uncomfortable and sought out opportunities to touch him; innocent touching, tapping his hand, that kind of stuff. John got the message and soon was reciprocating. I was getting excited.

I knew that John was enjoying the attention so after finishing my last drink I paid my tab and bid him good night. I could see the disappointment on his face when I stood, however, I purposely left an extra room keycard on the bar, you know, the one that comes in small envelope with my room number on it. Once I got to my room I left the door unlocked and took a warm shower.

I was just buzzed enough to close my eyes and let the warm water do its magic; I was so relaxed. While drying myself I heard a knock on the door; I was hopeful it was John. I left the bathroom and headed toward the door to find John inside. I was fresh out of the shower and wearing only a white bath towel. John said "I think you left this by mistake," and handed me the room key. When I reached out to take it he swiftly pulled me toward him and kissed me. Within seconds John had removed my towel before I knew we were bed.

John was the kind of lover that I hoped he would be, skillful, passionate, and creative. He had amazing stamina but most importantly, he focused on pleasing me. He wasn't in a rush to get off and spent lots of time with foreplay, kissing, and touching. I came twice before John he even touched my pussy!

As amazing as John's fingers were, his mouth and tongue were even more amazing. He teased me with his tongue, sliding it in and out of me in between long, slow licks. He occasionally took my clit between his lips for a few seconds, gently sucked, then returned to lick the length of my slit. John would occasionally divert his attention away from my slit and begin kissing my inner thighs. He did this over and over again for at least an hour, and when he inserted two of his fingers inside I came hard on his fingers. Before he was through, John brought me to three more wonderful orgasms.

When John fucked me he did so very slowly, inch by inch. Once deep inside of me John rotated his hips in circular motions rather than simply pounding me, and those movements sent waves of pleasure though my entire body. He occasionally pulled his cock out of me so that the just tip of his head was inside my opening, then penetrated deeply before repeating the action. He did this over and over again, making me come a couple more times; he had incredible stamina and self control.

I was exhausted from coming so many times, so decided it was time to return some of the pleasure. I rolled him onto his back and we kissed for along time. My right hand made its way down to stroke his shaft while we kissed, followed shortly by my mouth and tongue. I really wanted to please John, so I treated him to one of the longest, wettest, blowjobs I had ever given. I positioned myself between his legs and began lightly grazing his shaft with my fingernails. I kissed and licked his balls while caressing his cock, occasionally running my tongue along the entire length of his shaft. I teased him for a long time and when I finally wrapped my lips around his swollen head and took him into my mouth, John came immediately. I swallowed as his first ejaculation hit the back of my throat; he was so turned on for so long. I swirled my tongue around his head while his warm semen spurted and dripped out. I swallowed all of John's cum.

I kept sucking and licking John's cock until he was hard again. Using only my mouth, I continued bathing his cock with my mouth and tongue, bringing John to the brink or orgasm several times. I wrapped my lips around his head and slowly engulfing his shaft. Taking him deeper and deeper into my mouth, inch by inch, I felt his penis pulsate again, and I knew he was close. I bobbed my head up and down very slowly and stroked the bottom of his shaft with my thumb and index finger. I heard John groan, and when I inserted a finger just past the opening of his anus, his penis throbbed in my mouth and he erupted again, filling my mouth with his warm cum. I kept my lips wrapped around John's head as several streams of warm semen filled my mouth. I was so aroused that I came too.

As I look back, my evening with John was one of, if not the most satisfying experiences I have had with a man and John told me I had given him by far the best bj he had ever had; music to my ears!

Wednesday, March 23rd, 1994 -- An Officer and a Gentleman

I spent my twenty-forth birthday on a Caribbean cruise with my best friend Lisa and my older sister Ann. It was my first cruise and my first time in the Caribbean. I was pleasantly by all of the attractive people on the ship, and was especially taken with one cute guy, the ship's navigation officer. I just love men in uniform especially white uniforms like Richard Gere in 'An Office and a Gentleman' or Kevin Costner in 'No Way Out'. They're just plain sexy.

Sean was tall and thin with sandy blond hair and a sexy smile. It was clear right from the start that there was a mutual attraction. Sean flirted with me every chance he had. He sought me out during the day and somehow managed to find me at night when he was off duty. I loved the attention and kept an eye for Sean throughout the trip.

One night while off duty Sean joined Lisa, Ann and I for an evening out in Cozumel. We went to Senior Frogs, popped some tequila shooters, and had a blast. One thing led to another and we found ourselves making out on the beach. When Sean suggested that we head back to the ship, I was all in. I quickly told Lisa and Ann that Sean and I were returning to the ship and that I probably wouldn't see them again until the next day.

Once on board we circled the ship a couple of times before heading for Sean's cabin. Once inside we immediately embraced and Sean had removed most of my clothes before the door was even closed. We tore at each other like two starved animals; I had never experienced this level of lust before. I went down on him while he was standing in front of the doorway. I uncharacteristically took his entire length into my mouth and sucked him fast and deep. To my chagrin, Sean spun me around, removed the rest of my clothes, and entered me from behind. Sean fucked me hard and fast and came right away.

I never had sex like that before, so animalistic. Simply put, the man could fuck, and we fucked all night long. Sean had a big cock, the biggest I'd had to that point, and he filled me like no other man had filled me before. I also remember that Sean came like five or six times. I was never with a guy that came more than three times in one night. It was pretty amazing and when I stood and his cum literally oozed out of me and ran down my thighs. That was kind of hot.

I left Sean's cabin early the next morning and went right to bed. I looked for him the following day but he was nowhere to be found. When I finally spotted him later that night it he was aloof and distant. I also noticed him flirting with other girls as well. Looking back, I was obviously nothing more than just another object for Sean's trophy case. Unfortunately I believed that Sean thought that I was special; lessons learned. Anyway, it was a hot encounter.

Friday, February 5th, 1999 -- A Woman's Touch

I was twenty-nine when my best friend Lisa and I decided to take vacation in Jamaica. Unfortunately Lisa got really sick with the flu the day before we were scheduled to fly so I had to decide whether to cancel the vacation or go alone. Since the trip was already paid for, and with no insurance, I decided to go alone and make the best of the trip. As it happened, I made the right decision.

The island, hotel, and beach were beautiful and I enjoyed a couple of quiet days to myself. On the third day I went to the beach and pulled up a lounger next to Natalie, an attractive, petite brunette with ravishing brown eyes and a bubbly personality. Natalie was vacationing alone as well and we hit it off right away. Over the couple days we spent a good deal of time together sunbathing, shopping, and dining. We learned that we had quite a bit in common, same age, similar ethnicity (we were both Italian), grew up in the northeast, and attended catholic elementary schools. It was nice to have someone cool to hang out with.

We went out a couple of times to some of the bars near the hotel. On the second to last night of the vacation we decided to go into town to his some of the dance clubs. We got decked out in some sexy dresses and found a great nightclub that the hotel concierge recommended. Natalie is barely five feet tall, slightly taller with heels, and maybe weighed 100 pounds, and looked really hot wearing a low cut bright red flimsy dress; I knew that her smooth tanned skin and shapely legs would turn some heads. We had a blast dancing, drinking, and flirting with guys. As the night wore on and the alcohol kicked in we danced and flirted more. I was convinced that one or both of us would go home with someone.

We were pretty buzzed and at one point we were slow dancing with each other, and putting on quite a show. Our dancing became more erotic and we were dancing pretty closely, much to the delight of several onlookers. With the crowd urging her on, Natalie placed her hands on my hips and began grinding me from behind. I got into it and put my hands around her hips and pushed myself back onto her, my head falling back onto her shoulder. It was really hot and we were getting pretty turned on, especially with the crowd looking on and cheering.

When the music ended we took a well deserved break at the bar. A couple of young guys came over to hit on us and bought us drinks. I all but figured we'd bring them back to the hotel with us but Natalie had other ideas in mind. She leaned over and suggested that we head back to the hotel, just us. I was surprised by her suggestion but figured she was just tired or too drunk. I agreed and we left the bar while our two studs pouted in their beers.

We flagged a cab and instructed the cabbie to take us to our hotel. I hopped in the back seat and sat near the driver's side door. Natalie sat real close to me, our shoulders touching. I could smell her sweet perfume. There was plenty of room in the back of car for her sit and although I could have asked her to slide over, I wanted her close. With the sexual tension was building, Natalie put her head on my shoulder and placed her hand on my exposed thigh. A warm sensation welled between my legs as her fingers lightly tickled my inner thigh. I turned my head, looked right into her big brown eyes, and kissed her. Natalie's lips immediately parted and our soft tongues swirled in and out of mouths. We made out all the way back to the hotel, giving the cabby a real show.

We walked through the hotel lobby toward the elevators, and once inside the elevator we began kissing again. When the elevator doors opened we broke our embrace and I followed Natalie to her room. Natalie unlocked the door and I entered. She followed close behind and immediately stood behind me. She gently began removing my dress. Her soft lips followed her fingers as unzipped my dress. Starting with back of my neck she kissed my upper back with gentle pecks. Once my dress felt to the floor she undid my bra and cupped my freed breasts in her soft hands. She then slid my panties down to my thighs and I watched them drop to my ankles. Completely naked, I turned her around and kissed her as she removed her clothes.

We lay down Natalie's bed and snuggled. It felt good to be close to Natalie but before we went any further I admitted to Natalie her that I had never been with another woman before. Natalie said that understood if I wanted to get dressed and leave, but would love for me to stay. I told her that I wanted to be with her and Natalie suggested that I lay back and do what came naturally. We then kissed and petted for a really long time; the kissing was so tender and hot.

I got really turned on when Natalie sucked my nipples. By the time that she made her way between my legs I was dripping. Natalie touch was magical. She kissed and licked my inner thighs and beneath my kneecaps before gently parting my lips and tracing the outline of my pus with her tongue. She licked me in ways that I've never been licked before, gently and lovingly, and I came almost immediately when her lips and tongue finally found my clit. Natalie brought me to several orgasms that night.

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