Fantasies Cum True

My day of meetings had been intense, and I was looking forward to a quiet dinner in the hotel’s restaurant and then a peaceful sleep before heading home the next day. When I reached the restaurant I learned that a convention was in town and therefore I had to wait till a table was ready. I was pleased, however, when I was finally taken to a two-person table in a quiet corner of the restaurant near the front.

I was sipping a glass a wine and had just started to read the menu when the waiter came to ask if I would mind sharing my table with another guest. The waiter directed my attention to the waiting area where an attractive slim woman in her mid-forties was standing with a rather impatient expression on her face. She was dressed in a business suite with a knee length skirt and elegant white blouse. After glancing at the woman I shrugged my shoulders and agreed to share my table. I figured that it would be more fun than eating alone, but I had no idea what this accidental dinner guest would lead to.

The waiter showed the woman to my table, and I stood to greet her. Her name was Mary and she was also in town on business. Like me, she was also a bit annoyed with the cowed caused by the convention. At first she expressed no interest in conversation, and I almost gave up trying but tried one last time by asking if she would like to share a bottle of wine with me and that it would be my treat. Mary paused, cocked her head to one side considering my offer with a half semi-smile held tight across her lips and then accepted my offer with gratitude and a friendly smile.

After we toasted the evening with her first sip of wine she seemed to relax. As we perused the menu I made small talk, asking her about her day and what she was in town for. Before responding to my questions, she turned the conversation to the menu and we compared thoughts on the different selections. Soon we chose similar meals and the waiter returned to take our order. The starters arrived promptly, and I poured a second glass of wine for both of us. Soon Mary was smiling and laughing as I told her about an amusing experience in a meeting that day.

The conversation warmed as the wine and jazz piano had its soothing effect on both of us. It turned out that we both worked for non-profit organizations and were in town seeking funding from the same foundation. We compared notes on our experiences and made friendly wagers about our chances of success. As the second glass of wine came to an end our dinner arrived and the waiter poured a third and asked if I wanted to order a second bottle. I raised my eyebrows in question to Mary who laughed and exclaimed that she might as well since she was only flying home tomorrow and deserved to unwind from the day’s hard work.

As we ate slowly and drank the wine our conversation became more friendly and intimate. We started sharing stories of our youth, the trials and tribulations of teen age dating, and our first sexual experiences. We laughed at our childish pranks and toasted our experiences with skinning dipping and sex on the beach. With a quiet question from Mary our conversation turned to our sexual fantasies. I must have blushed because Mary giggled and pointed at my face saying that the question must have touched a sensitive nerve. I tried to regain some composure with little success till Mary came to my rescue offering to share one of her fantasies. She leaned over her plate and motioned me close as she spoke in a quiet soft voice that was barley audible.

“One of my fantasies,” Mary breathed as she looked around to make sure none of our neighbors was watching, “is to ….” She stopped and covered her mouth with her hand as she spoke saying that she couldn’t tell me because she know I would be shocked and would laugh at her. I assured her that I wouldn’t be shocked and that I wouldn’t laugh and urged her on. She made me promise not to laugh before she started to speak again. Finally she leaned forward again and spoke in a voice I could hardly hear. I leaned close holding my tie to keep it from flopping onto my plate.

Mary cleared her throat and smiled at me in a way that I found very exciting. “One of my favorite fantasies,” she began again, “is to… mmmm. Now don’t laugh! Is to watch a man … mm I can’t dam this is too embarrassing!”

I tried to assure her that it would be okay and that I wouldn’t laugh as my mind raced with excitement. Could it be that she and I shared a similar fantasy!

Mary started again, “I fantasize about sitting in a room fully dressed as I order a man to strip nude for me and masturbate!” She spoke the last part quickly looking down at her plate and when she finished she said, “There, I told you! Oh God, how embarrassing?” Mary exclaimed as she took a deep drink of wine and refused to make eye contact with me. Her hand shook as she returned the glass to the table.

My mind was a flame! I couldn’t believe what I had just heard. How could such an attractive woman share the reverse of my favorite fantasy? I was so stunned it took me what seemed for ever to regain my composure and react to Mary’s worried fidgeting as she said under her breath, “God you must think I’m crazy or weird or something? Maybe I should just pay for my meal and leave.” Mary made a motion toward the waiter and I quickly reached across the table to pull her hand down with mine and squeezed it gently as I signed the waiter to stay away and finally spoke.

“No, please Mary don’t leave, and I don’t think you are crazy! In fact I find your fantasy extremely exciting. In fact, I explained, it is the exact reverse of mine!” She paused and looked at me intensely for a moment, then her face turned angry.

“You are just saying that to make me feel better! I don’t like to be patronized!” She exclaimed as she started to tug her hand away from mine.

“No, I’m not just saying this to make you feel better!” I have had this fantasy for many years and have had the supreme pleasure of actually acting it out on a few occasions!”

Mary’s face jerked up and her eyes were wide with interest. “Really?” she asked as she leaned forward. “Have you really had such an experience? Have you really masturbated for a woman as she watched and ordered you to perform?”

I nodded my head up and down and said yes as I felt my face burn with a deep blush. Mary smiled and giggled quietly her eyes sparking with mischievous excitement.

“Tell me about one of these experiences!” She commanded firmly as she removed her hand from mine and took up her fork to eat some of her meal that was turning cold.

I reached and took a fork full of my rice and chewed it slowly trying to compose myself and decide which of my experiences I would share with her. She urged me on with a smile and a nod of her head. I could feel my cock swell as I looked at her bright eager eyes and sensuous lips. I imagined myself for a moment standing before her naked and masturbating and found that my cock was suddenly fully erect. I wiggled in my chair and explained that I was finding this very stimulating.

Mary smiled excitedly and asked if I was becoming as excited as she hoped I was. I smiled and shook my head and shifted in my seat again. Mary giggled with glee and told me again to tell her about one of my experiences. She also asked me to move my chair to the left so that she could see if I was telling the truth about being excited. I smiled back at her and moved to the left she leaned over and her eyebrows rose and her smile widened as she saw how clearly excited I was.

I decided to tell her about the time when I was working as a maintenance man at an apartment complex while in college. It was one of my first experiencing masturbating for an older woman and one of my favorite.

I explained that I had a job as a maintenance man at an apartment complex while in college. Once day during my weekly afternoon shift, after I had just come on duty, a single woman tenet, who had quite a reputation, called to ask for my colleague to come up to change some light bulbs. When I told her that Dan was not around at the moment she seemed frustrated, and so I offered to come up to help her. She asked me how old I was and when I told her that I was 20 she seemed to brighten up and eagerly accepted my offer of help.

When she answered the door I found that she was dressed rather proactively and moved in very suggestive ways as I worked in her apartment. She mad sure that I could see her hard nipples down her blouse as I looked down at her from the ladder to ask for a new bulb. I blushed as I felt my cock grow hard and push against the tight fabric of my jeans as I looked at the selling of her breasts from the ladder. The woman wasted no time and let her hand slide up my leg to my crotch and squeezed my cock. I nearly dropped the bulb and coughed in surprise. But she received the reaction she was seeking as my cock grew harder and pulsed with excitement. She fondled and squeezed me some more as I stood on the ladder in amazement trying desperately to screw in the bulb. When the light finally flashed on she released me and urged me to come down the ladder. I hesitated not sure what was in store for me.

As I folded the ladder and leaned it against the wall the woman had slinked her way to the couch where she sat in front of me very suggestively. I just stood their staring at her my cock throbbing and my mouth ajar. Her face turned stern suddenly and she leaned forward. She spoke in a deep quiet voice that was oddly menacing and ordered me to strip in front of her and to show her my cock.

I paused to take a sip of wine and said, “This is too strange, maybe we should just finish our dinner and call it an evening. I’m sure I’m boring you with this strange story and you must think that I’m crazy or something.”

Mary also took a sip of wine but her meal remained untouched. “No! Please don’t stop! I’m totally fascinated by the story and am become very excited! Can’t you see my erect nipples?” As she asked this last question she pushed out her chest so that the soft silky fabric of her blouse was stretched tight across her chest to accentuate her hard nipples which were clearly visible.

I smile and blushed a little as I licked my lips with pleasure. I took another sip of wine and returned to my story.

“Now, where was I? Oh yes the woman had just told me to strip for her and I was standing in shock trying to understand what was happening. I blinked in disbelief and asked her what she had just said. She spoke up a bit as her face became even more intense her eyes burning into me as she hissed, “Take off your fucking clothes college boy! Do as you are told now or I will yell rape and you will be royally fucked!!” She then smiled sweetly, and told me that if I didn’t want all that trouble I should just start taking off my clothes for her by the count of three.

She started counting and just as she said three I unfastened my belt in a rush too scared to do anything else. She smiled and told me, “Now that wasn’t bad at all was it?”

I just nodded my head in agreement and continued. Before long I was nude and standing in front of her. I was surprised that I was still fully erect even though I could feel my face burn with embarrassment. She smiled at me and congratulated me about my nice erection. She then told me in a very firm voice to start playing with my cock. I touched my self and moaned with pleasure and jerked a bit as a surge of pleasure shot through my body. She urged me on using her hand motion to tell me what to do. I started to stroke my cock as I stared at her staring at my cock she massaged her breasts and pussy as I started jerking quickly. She then ordered me to play with my balls with my free hand as I jerked harder. I could feel that I was about to cum when she shouted for me to stop. I groaned in frustration eager to explode, but she shouted again telling me to do what she asked. I finally consented and released my cock to sway before me as the desire to climax surging through my body.

She had me walk around her and then up close to her so she could caress my cock and balls. As she touched me I nearly exploded my cock jerking and my balls churning with excitement. She ordered me to spread my legs and looked up into my face as she raked her long fingernails over the tight wrinkled skin of my scrotum. My hips thrust forward involuntarily as she cupped my balls and rolled them around in her hand. Then she ran her finger nails along my shaft and encircled my cock head and squeezed. I moaned loudly with a mix of pain and pleasure. Without warning she wrapped her hand around my cock and jerked me hard a few times. I felt my climax rise and thought I would explode on her when she stopped and pushed me away.

She then ordered me to lay down on the floor so that she could straddled me. She squatted down toward my face, and I realized that she had no panties on as her smooth shaved pussy opened up before me. She lowered herself down so that I could smell her sex and see the glistening folds of skin. She then push down on my face and I raised my head to meet her pussy licking and sucking hungrily. She ground her pussy down on my mouth and started rocking back and forth as she massaged her clit. It didn’t take long for her to cum and her juices flooded over my face. She lingered over my face for a while as I licked and sucked her then she rose up and off of me to sit beside me. She then ordered me to start jerking off slowly. She had me use both hands, one massaging my balls the other stroking my cock slowly. Her hands caressed my chest, stomach, legs and occasionally joined my hands on my cock. I warned her that I was going to explode and she told me that I could cum for her. As she finished her sentence I exploded with a loud groan and a massive stream of cum burst from my cock to arch over and fall to my stomach. This was soon followed by another and then just small spurts and dribbles oozed from my cock as I jerked like crazy hopping for another orgasm. She smiled at me and urged me on as I jerked like crazy spurting cum. When the last drop was expelled she looked down at me and ordered me to taste my cum for her. I eagerly complied as she smiled. She then left the room to wash and moments later she appeared dressed in jeans and a sweater. In an off-handed matter she told me to clean myself up and leave. When I came to the door to leave she called my name. I turned to see her smiling at me and waited. She winked at me and said that I should drop by again in a day or too if I wanted to please her. I nodded eagerly smiled sheepishly and left the room. For the rest of the school year I would drop by her apartment about twice a week to let her use me for her pleasure.

I hadn’t realized how long I had taken to tell my story and apologized to Mary for going on so long. Now it was Mary’s turn to consol me as she reached across the table to touch my hand and assure me that she had enjoyed every bit of my story. There was an awkward pause in the conversation and then I offered to top off her wine. She eagerly accepted and we both took a sip in silence. I was hopping that she, like me, was contemplating asking me to repeat this experience for her. As I stared at the table cloth and swirled wine in my mouth Mary spoke up in a barely audible tone. “Would you like to masturbate for me?” I glanced up quickly but Mary was looking down at the table. I didn’t hesitate and told her that it would be fantastic to make her fantasy and mine come true. Mary glanced up and said, “And no pun intended either I bet.” We both laughed and drank more wine.

I then asked if she wanted to come to my room or if she wanted me to visit her in her room. She paused for a moment to think and finally said that she would be more comfortable in her room.

The remainder of our meal was now cold and neither of us was interested in anything but getting to her room. I called for the bill, and insisted that I pay for her dinner. We were rising from our chairs as I signed the bill and it took all our will power to not run from the restaurant.

I followed her, enjoying the sight of her slender rear moving beneath her skirt as we walked to elevator. We were both pleased that no one else was waiting to go up so we had the lift to ourselves. I was completely excited and the bulge in my pants was very visible. Mary noticed and commented that it looked as if I was looking forward to something. We both giggled as I felt my cock throb and twitch in my pants. Mary simply stared with pleasure. I had hopped she would reach out and touch me but she didn’t.

Finally, we reached her floor and walked quickly to her room. Her hands were shaking as she tried to insert the key card and it took a few tries before the green light appeared and we were able to enter. She had a nice suite with a separate sitting room and bedroom. She excused herself and went to the bathroom. When she returned I asked if I could use the bathroom and clean up. She smiled and said that she would grant me this privilege. It was clear that she was warming up to her role. I thanked her and quickly left.

After taking a pee I washed and dried my cock and balls and used some hand cream on my cock so that it would be smooth and shiny. I dressed and return to the room.

She had moved a chair to the center of the room and was sitting there with her one leg crossed over the other. She had a stern look on her face and I felt the excitement rise inside of me. My cock quickly swelled and pushed against my pants. My mouth went dry with excitement and anticipation as I stood before her. As she looked me over I asked her how I could please her.

She hesitated and finally told me, “Well, I guess you should start taking off your clothes for me and show me your cock and balls.” As with all other experiences, I had this wonderful sense of embarrassment and thrill as I started to take off my clothes. I first kicked off my shoes and then quickly unbuttoned my shirt. I then undid my belt and pulled my pants off. My cock surged forward making a funny tent in my briefs and I stopped to stand before Mary in my underwear. She stared at my erect cock and then looked up into my face. Her face had a mixed look of embarrassment, excitement and power. She hesitated and I suggested that she could use swear words if she wanted to when she ordered me around. She nodded her head slightly and then spoke to me is firm even tone.

“Ok, fucker, remove your underwear and socks and stand in front of me nude. Let me inspect your pitiful cock and ass!” She giggled as she covered her mouth and a sheepish look spread over her face as she struggled to appear tough.

I eagerly complied feeling the rush of excitement flood through me as my cock sprung free to sway before me. As I scuffed off my socks I inched forward to stand about two feet in front of Mary. I wanted to start stroking my cock for her but I resisted the temptation as I watched Mary look at me. Mary made a turning motion with her hands and I turned around. When my ass was facing her she told me to stop and ordered me to bend over and spread my cheeks for her. I did as she ordered spreading my legs and my cheeks wide. I nearly fell over when I felt her hands grab my cock and balls from behind. My body jerked and I moaned as she fondled me. She slowly stroked my cock with one hand as she gently squeezed my balls with the other. She asked me if I liked this, and I simply moaned with satisfaction. Then she started squeezing my balls harder and jerking my cock vigorously. The situation soon shifted from pleasure to an uncomfortable feeling mixed with pain. I started to complain and she just laughed as she squeezed hard and then released me. I nearly fainted as I felt my balls being crushed and a great sigh of relief escaped from my clenched teeth as she released me and slapped my ass hard several times as she ordered me to stand and face her again.