I received a lot of request (surprisingly by younger females) who want stories written about them with older men, bosses, boyfriend's fathers, uncles, etc. This special request came by a young reader who asked if I could publish her story for her. Stacey is like a lot of teenage girls who have reached out to me and have shared their experiences about being with a much older man. A lot of these teenage girls are very ambitious and have a certain confidence and maturity beyond their years. The common thread that runs between them is a turn-on for confident, powerful older man. Their praises include their wealth and power and how sexually advanced they are and that they are exceedingly more endowed then their boyfriends or guys their age. Every word in this teenagers experience is her own. Through questions I prompted as we went through the time-line of her experiences was how her story got here.
My name is Stacey. I am an 18 year old senior that goes to a private High School in NYC. As part of an internship program I work in a very powerful law firm in the city that specializes in commercial land development and real estate properties.
Coming to work directly from high school and experiencing the dramatic change from the immature acting boys to these older men of power began to make me think about what it would be like to be with a much older man. Working so close to these older men with their take-no-prisoners personalities and their wealth and power really began to excite me and seeing the entire older attorney's constantly leave for lunch or dinner with a girl, not much older than myself added to my curiosity.
About me. I stand 5'5" tall and weigh 108 pounds. I have long blond hair and my measurements are 34D-21-33. I wear braces, which in my school uniform or cheerleader uniform gives me a very innocent look. After school I always go to my apartment to change into professional cloths for work. I always dress fashionably for work, in short pencil skirts that show my narrow waist and my tapered legs. I always wear sheer blouses that show my sheer, lace bras (white or black) and always wear tan, black or nude thigh-high stockings with black or brown pumps to accent my legs and to add a sexy quality my outfits.
I admit that I love the compliments and looks I get from the older men in the firm and have enjoyed going to dinner with a few of the older attorneys to very up-scale restaurants when they were meeting clients. Being right beside these older men and listening to them talk about taking over companies or building multi-million dollar luxury buildings in the city and around the world made me think about what it would be like to be with them.
The excitement that surrounded these men was infectious. Sitting beside them in their private limousines as they dropped me off after dinner made me feel so special, and when I watched them look at my body as we talked sparks went right through me. When they told me how sexy I was and how mature I was it always had me instantly thinking about what it would be like to be in his bed. They always escorted me to the lobby door and gave me a kiss after they thanked me for coming that night; a few of the older attorneys letting the kiss linger before they walked back to the limo.
When that happened, the instant my lips met theirs I felt a tingling excitement run through my body that I never experienced before. Each of those nights always ended with me stripping to my stockings and high heels and lying on my bed rubbing my breasts and nipples with one hand as I masturbated to the fantasy of being in bed with the older attorney that kissed me that night.
Although I have a steady boyfriend in High School I admit to cheating on him and sleeping with three older men. The first man was a wealthy land developer that did business with the firm. His name was Jack Travers. I had just turned 18 a month ago and was assisting one of the firm's younger attorneys when I met the 80 year old land developer.
When I was introduced to him I immediately thought to myself how handsome and totally distinguished he was especially for his age. As I was introduced to him I watched his eyes scan my body from head to toe and as he did I instantly felt the room temperature go up 100 degrees as I felt my I felt my skin get real hot and felt my nipples get instantly hard in my sheer, lace bra. I was so impressed with the way he conducted himself in the meeting and had an instant attraction to his personality and confidence. Like a lot of the older men in the firm or that do business with us, he was tall with a slender build and had wonderful white hair and chiseled facial features. They also all were extremely confident and I could tell that they had strong personalities.
During the meeting I caught his eyes taking more than quick glances at me, in fact he looked at me from head to toe with complete indifference to the firm's attorney who was there. When we made eye contact I could see the hunger in his eyes and would purposely re-cross my legs and watch his eyes travel to my legs. Sensing he knew exactly what I was doing he shot me a knowing grin and I returned it with a knowing smile.
In the meeting he learned that it was my 18th birthday and that I was going out with my boyfriend to celebrate. A half hour after the meeting two dozen roses were delivered to my desk with a card that read, "Cancel your plans with your boyfriend. I'm going to spoil you rotten tonight. Jack."
The second I read the card my heart started racing in a way I never experienced before. The confidence in his words; more commanding me than asking me had my body trembling with excitement. I began to get really excited at the thought of going out with him.
Up until now the idea of being with an older man was purely fantasy and wishful thinking on my part, but now being confronted with the reality of it I was tingling all over as I pictured Jack and I together. I admit that the thrill of him wanting me and the realization of him being 62 years older than me added to my excitement.
Without any hesitation or guilt I called my boyfriend and told him I had to work late on a project that had a deadline. Although he was a little annoyed I said that I would go out with him on the weekend to celebrate my birthday. As I talked to my boyfriend all I could think about was Jack and that I was going to be with a man who was 62 years older than me.
I knew that this would be cheating but all I cared about was the excitement I felt about being with Jack. Although I knew I should have felt guilty, I didn't have an ounce of guilt and as soon as I hung up with my boyfriend I called Jack on his private cell phone thanking him for the beautiful roses and accepting his invitation.
When he asked if I canceled plans with my boyfriend already I told him I did.
"Any quilt or second thoughts?" he said in a deep confident voice as if knowing what my response would be.
"Oh God, I couldn't wait to cancel on him," I said without any hesitation.
"A sexy 18 year old who knows what she wants. I like that quality Stacey. I like it a lot," he said with authority, which turned me on like crazy.
That night was amazing, starting with him taking me to an exclusive restaurant in the city that I knew was impossible to get a reservation for. Dressing for my date was unlike any experience I ever had. In the shower my body was electric, as a tingling sensation flowed all over my skin as I thought about my date with Jack. Every time I washed my breasts and made contact with my nipples I nearly came.
The thought of me being together with such an older man had my hands running all over my body as I closed my eyes and imagined us kissing and even becoming intimate with each other. As I dressed for our date I felt so sexy. Every item of clothing I put on was with him in mind, especially my sheer, white bra and tiny, satin thong.
As I put on my nude thigh high stockings, sheer white bra, and silk thong all I could think about was him seeing me this way. I decided on a sheer white blouse that showed every stich of my lace bra and a tight pencil skirt that went way above my knee and showcased my long, tapered legs. After stepping into my 4 inch black high heel pumps I looked in the mirror and smiled at myself approvingly with a sly grin.
When I came down to the lobby and saw him standing tall and inpecibally dressed in a very expensive black jacket and slacks with a crisp white dress shirt that clung to his slim chest I nearly melted. After taking in my outfit he told me how sexy I looked and took my hand and led me to his limousine where his driver was waiting to open the door.
Once we were in his private limousine he opened a very expensive bottle of champagne and made a toast to me being 18 and very sexy. After the toast he leaned in and gave me a soft, brief kiss. I can't tell you how sexy I felt the second my lips made contact with his. Although the kiss only lasted a second it sent sparks right through my body and set the tone for the evening.
As we rode to the restaurant we talked about what he had planned for the night, which included a ride above the city in his private helicopter. As he talked we began playfully kissing. What started as our lips touching and our tongues meeting briefly turned into our tongues twisting across each other's as our lips touched softly. I was going crazy in every way as I felt my body more turned on that it's ever been before.
During dinner the chemistry between us was building by the second as we shared sexy kisses. During each of these kisses his hand went up my crossed stocking covered leg right to the top of the lace trim. As his finger traced along the trim touching the bare part of my skin I would groan, "Umm," from the thrill he was sending through my body. When we kissed my heart was beating a mile a minute in anticipation of what might happen between us.
After dinner we rode in his limo where he took me to helipad where is private helicopter was waiting for us. The cabin was luxurious with a long cushioned sofa. During the ride the intimacy grew between us as we shared playful kisses that turned into deep, passionate kissing as our tongues explored each other's hungrily. As we kissed his hands ran up and down my stocking crossed legs which had me so turned on. Hearing him say how sexy my body was had me moaning softly. As his hands roamed up and down my stockings sparks were shooting right through me. His touch alone made me hungry to kiss him.
Taking a ride high above the city in his private helicopter was so impressive. He put his arm around me and told me how sexy I was then opened a very expensive bottle of champagne and made a toast to me being 18 and being very sexy. I was so captivated with him. When he leaned in we started kissing again as our tongues explored each other's heatedly and with an incredible hunger.
It was as if we were lovers as our mouths were open and our tongues flicked across each other's slowly. It was such a sensual kiss. I never kissed like this before and it felt so naughty and so right. To me it was the sexiest thing imaginable and he being 62 years older than me made it even hotter.
I can't begin to tell you how sexy and alive I felt. Here I was just turned 18 that day in a deep, sensual kiss with a 80 year old man I had met a few hours earlier. A part of me felt so devilish to be kissing a man 62 years older than me. It was such a naughty kiss the way our tongues were out of our mouths flicking wildly across each other's. As we kissed his hands were roaming all over my stocking crossed legs which had me moaning.
