First Time and Many More Ch. 01

She was in her late 40s, I was still a teenager. She was one of my mother's best friends; I was a perpetually horny young man who would have screwed a snake if I could get someone to help me hold it. First, a little background:

I had been infatuated with this woman for about as long as I could remember. Certainly since I figured out how to masturbate and started to have some serious fantasies about women. Note I said "women" and not girls. At the time, I had absolutely no interest in any girls even close to my own age.

Like I said, she was one of my mom's good friends and lived two houses down the street. Her name was Barbara. Barbara, my mother and several other women belonged to a bridge club and they played cards at least twice a week. Many of those card games were at my house. Barbara always seemed to dress nicer than the other women did. Some of the other ladies were very casual; they wore shorts, and occasionally even had curlers in their hair. Barbara always looked and dressed nice. Dresses mostly but an occasional pair of slacks and a blouse or sweater. I don't believe I ever saw her when there wasn't an ample amount of cleavage pushing up from her sweater or blouse or dress. And she had more than her share in the breast department. The ladies sat at the table in the den and played cards for hours on end. I'd hang around trying to be discrete as I caught a glimpse of cleavage, smelled their perfume, and watched them smoke their cigarettes. I'd have to leave if the bulge in my shorts became too noticeable. Usually I'd head back to my room for a furious masturbation session. If the seating arrangement was right, I could open my bedroom door just a crack and see all the way into the den. From that vantage point, I could watch Barbara as she smoked and chatted and played cards. I lost count of how many times I blasted the inside of my bedroom door with a big load of cum.

All this peeking, fantasizing and masturbation had been going on for a few years. As I said, these fantasies really got going when I learned how to masturbate. As time went on, the fantasies and masturbation sessions became stronger and stronger. One day, I got a crazy idea. If I could get into Barbara's house, then the fantasies would be even more exciting and the possibilities would seem endless. Since I'd been watching the ladies for years, I knew exactly how long they played cards each day. After first phoning Barbara's house to make sure no one was home, I wandered down to her house and was able to let myself in through the back door. It was HEAVEN. Everybody's house smells different...not bad, just different from your own. As soon as I walked in the door, I had a raging hard on. I wandered down the hall into her bedroom and then into her dressing room. Even though I knew I had plenty of time, I couldn't control my urges. I dropped my shorts and briefs and started to stroke. Standing there in Barbara's dressing room I only lasted a few minutes before I erupted all over the vanity top. I was so dizzy I had to sit down for a moment. I quickly cleaned up my mess, pulled my shorts back on and left, having been in her house only about 10 minutes, but what a 10 minutes it was. I was hooked! The thought of being in her home, around her things and especially the smell were the most exciting thing I had ever done and I could not wait for my next opportunity.

I didn't have to wait long. Early the next week, my mother mentioned the women would be playing cards at the house that afternoon. This time, I headed for Barbara's while the first hand was still being dealt. Now I knew I had at least two hours to explore and play. Explore I did. I learned that Barbara wore a 38DD bra and she had a very extensive lingerie collection. She had more underwear in her one very large lingerie drawer than I had ever seen in my mother's and sister's drawers combined. All colors, all materials and man did they ever smell nice. However, the real find was in her closet. The closet was a huge walk-in affair almost as large as my bedroom and lined with cedar panels. That is where I found Barbara's furs.

I can't explain it, but furs and the women who wore them had always fascinated me. Even when I was much younger, I would walk close to women in their furs as we filed out of church on Sunday. I would be very near to the woman in front of me and would reach out and touch her fur coat. Some Sundays, if I was clever and the was crowd large, I could get three or four sneak feels before it was time to head for the car. When my parents had parties, I loved to sneak into the guest room where all the coats were laid out on the bed. There would always be several furs. I was too young to know why or what was going on, but I knew that I loved to feel and smell the furs. Even my very first successful masturbation session (the first time I actually had an orgasm and ejaculated) had been with a white, faux fur collar that belonged to my sister. Not knowing any better I wrapped the fur collar around my dick and rubbed back and forth like I was rolling out a piece of pretzel dough. There are no words to adequately describe the feelings a guy experiences with his first orgasm.

Now Barbara had three full-length coats, a mahogany mink, a sliver fox and a dark brown sheared beaver. One jacket (red fox) and a very long white mink stole. By this time, all I had left on was my T-shirt and my erection was leading the way. I caressed, rubbed, and buried my face in each fur in turn. If the smell of her house wasn't intoxicating enough, her closet and furs were even better. All the furs had a musky aroma from the fur itself plus a combination of her perfume, a little hint of her cigarettes. It was while I had my face buried in the white mink stole that I lost it. My knees got rubbery, my dick (which was already throbbing) twitched uncontrollably, and I came about as hard as I could ever remember cumming. Fortunately, I was able to shift my hips slightly. It was the only thing that saved me from blowing a huge load all over the white mink stole. Moreover, I had only been in Barbara's bedroom for about 20 minutes. I still had plenty of time to enjoy myself. It was the most orgasmic day of my young life. I had four intense orgasms over the course of a little over an hour; all of them in Barbara's closet and each one with my face buried in a different fur. I didn't actually stroke my dick; I simply rubbed against the fur all the while deeply inhaling the intoxicating aromas. After my fourth orgasm, I was exhausted. I cleaned myself up and used an old towel I found in the guest bathroom hamper to clean the cum off the floor. Then I quietly left Barbara's and went back to my house.

I arrived home just in time to see the other women driving off and when I walked inside, Barbara was chatting with my mother. They were both smoking and I swear Barbara was looking right at me as she took a long drag and capped it off with an amazing snap inhale. I didn't think it was possible after all the earlier masturbation, but my dick gave a big twitch in my shorts and my knees felt a little weak. Barbara made some comment to my mother about how big and handsome I had grown up to be. She looked me up and down from sandals to hair, and went right back to chatting with my mother and finished her cigarette.

My regular trips to her house were the highlights of each week. Later that summer, Barbara and her husband went on a two-week vacation and my mother volunteered me to look after their house. Can you believe that? My job mostly entailed taking in the newspaper and mail every day and making sure the plants were watered. The rest of the time, I spend buck-naked in Barbara's bedroom. My time to explore and play was truly unlimited and the orgasms too numerous to mention. Among other things, I found a long black cigarette holder way in the back of her lingerie drawer. Amazingly, I did not smoke and I still do not today. But, everyone around me did, my parents, both my sisters and most of the adults that were my parent's friends. Because of this, I was not new to the aroma and I definitely found the sight of a woman smoking to be erotic and arousing. That summer I even experimented with smoking in Barbara's house. Sometimes I would put together an entire outfit of her clothes, skirt, blouse, bra, panties, stockings, shoes and of course a fur. Then lie back on her bed and imagine she was undressing in front of me. Somehow, I never made it all the way to her being naked before I had an orgasm. I found a box of home movies, nothing exotic, just your typical home movie stuff. Nevertheless, the movies did provide even greater voyeuristic pleasure as I could now see and hear Barbara in the films as I masturbated with whatever had my attention that day. Many times, I was able to spend almost the entire day in her house. I will never forget that incredible summer. I was sorry to have them come home after only two weeks. After that, my time at Barbara's was relegated back to the occasions when she and the ladies played cards.

Now all this fascination and masturbation had been going on for years. One afternoon I came home after a going to a movie with some friends. Bingo, the ladies were having their regular card game. A quick glance at the clock told me I had about an hour to have some fun at Barbara's. In no time, I was in her bedroom. I dropped my sandals, shorts, and briefs on the floor near the bedroom door. I went straight to the closet and grabbed what had become my favorite of her furs, the sheared beaver. It was full-length, chocolate brown, and the most incredibly soft thing I had ever felt. Then I was on her bed with the coat, stroking, teasing, smelling, and rubbing myself into ecstasy. I don't recall why, but I was more patient and really took my time that afternoon. When I finally had an orgasm, it was incredibly intense. So intense that as I lay there in a post orgasmic bliss, with just the corner of the beaver coat over my crotch, I dozed off. And I was still in that very position and still asleep when Barbara came home and caught me.

Part Two

Barbara walked over to the bed and shook my arm. My eyes fluttered open and I'm sure the look on my face was comical although I felt anything but funny. She looked angry and asked what I had been doing, as if she didn't know.

She said, "You just stay right where you are" and walked into her dressing room.

I was sure she was going to call my mother. When she came back a few minutes later, she had lit a cigarette and she walked over to the window box next to the bed and sat down. I was dumbfounded. After all, here was the woman of all my fantasies sitting four feet away, smoking a cigarette and there I was, lying on her bed with nothing on but a t-shirt. She just looked at me and after a few minutes said,

"You've been doing this for quite a while, haven't you"?

I just couldn't find my voice and could only nod in the affirmative. Barbara said that she had suspected that someone had been in her house because things were often slightly different from the way she remembered leaving them. She said she was somewhat relieved to finally know who it was that had been in her home. She went on to say,

"Well I can't honestly say that I am not that surprised. "After all, I've been watching you watch me for years; looking at me as I played cards with your mother and the other ladies."

I must have looked shocked because she said,

"You thought you were being discrete, but I could tell you were watching me while I smoked and that you were always trying to look down my dress. "What did you do when you left? "Go to your room and jack off?"

I finally found my voice and said in a very sheepish voice, "yes maam." Barbara went on,

"Well, I must say that I find it flattering that a young man such as you finds an older woman like me so interesting." "What about today, earlier, before I came home, what were you thinking about?"

I just shrugged my shoulders.

She said, "Did you think about me?"

"Did you think about me smoking?"

"Hell, I'll bet you even thought about me naked while you played with yourself and one of my best furs." "Did you Pat?"

"Did you imagine me naked"?

Again, all I could do was nod. But I had a bigger problem. In spite of my situation, the woman of all my fantasies was sitting RIGHT THERE, smoking a cigarette and asking about my masturbation sessions. As unbelievable as it sounds, I was getting hard! And the corner of the beaver coat was still covering my growing erection. It took all my will power to try to stay still, but the delicious beaver was caressing my dick in its ever-growing state; and it was making me crazy.

Then Barbara said. "You know it's nothing to be ashamed about, masturbation I mean. Everyone does it and it is perfectly natural for a young man to feel all those urges and needs."

About that time, I think she noticed the growing bulge under the coat because next she said,

"Well, Pat, you know that you have violated my trust by being in my home without my permission." "As punishment, I think you should show me what you were doing before I came home."

My eyes went wide and I stammered,

"Oh, Mrs. Phillips, I don't think I can do that."

She said, "First of all, as intimate as you have been with my things, I think you can call me Barbara, and second, you can either show me what you were doing, or you can show your mother!"

Waves of embarrassment and shame passed over me. I couldn't believe what she was saying; she wanted to watch me jack off! My consternation was interrupted by her admonishment,

"Go ahead, SHOW ME."

Slowly, I reached my hand under the corner of the fur coat. I wasn't really jerking as much as I was trying to get the fur off my hardon that, by now, was starting to throb. Without saying a word, Barbara stood up and sat on the edge of the bed and said,

"NO, I Said I wanted to SEE what you are doing."

With that, she reached over and pulled the coat off my erection. I swear I hear her moan. Then she placed her hand on my stomach and began making circles and as the circles grew bigger, her hand got closer and closer to my erection. Now I was really throbbing and my dick twitched with each beat of my pounding heart. Barbara didn't say a word. She took the last drag off her cigarette and put it out in the ashtray on the nightstand. She turned back to me and ran her hand down my chest, over my stomach to the base of my cock. Pushing my hand aside, she wrapped her hand around my dick and started to stroke up. However, before she could reach the top, my hips involuntarily humped up into her hand and I had a massive orgasm. Cum flew everywhere, and I kept thrusting up into her hand. My orgasm seemed like it lasted forever. If I wasn't already mortified enough, now this. I just lie there, the spasms slowly subsiding and cum still oozing out of my dick. Barbara gave me a squeeze and looking me straight in the eye said,

"Well, my my.... hmmm, if you ever expect to be able to please a woman, you are going to have to learn much better self-control."

"Now, young man, if you can keep this a total secret, just between you and me, and swear never to tell a soul, I will teach you and help you learn some self-control".

"But you have to swear that you will NEVER tell anyone".

"Can you do that"?

I regained some sense of comprehension and managed to say,

"I promise."

Barbara said, "Ok, clean yourself up, get dressed and come back the day after tomorrow at 2:30."

I had an erection for the next two days. I had trouble sleeping and I didn't eat much. But you can bet your bottom dollar that I was at Barbara's door exactly at 2:30 on Thursday.