This is a true story about a vacation trip with a friend I met.
The Love of Masturbation-Charlie
Here is one story that I relive from time to time. I will post most of my experiences and any news that occur.
I was 22 at the time. One night I met up with a group of my friends. As soon as we walked in all eyes were on us. Six young females being loud and full of themselves and having fun. It didn't take long before three men old enough to be our fathers would yell and tease us. We returned the comments and it was all in good fun. We started to frequent the place and started to become regulars. One regular was Charlie. Charlie was divorced and always on the prowl.
Charlie of course was the biggest flirt and would flirt with each and everyone of us at every chance. However, the thought of doing anything with Charlie was never on our minds. Charlie would constantly joke that I should go with him on his business trip. I would always comment. Two rooms or one room? One room! Was always his comment. I would joke and say it would have to be somewhere nice! Every time he would tell me where he was going and I would say not nice enough.
Tuesday was ladies night and I arrived with my sister, sister's husband, a friend of my sister. As usual Charlie came over and started chatting with all of us. I had warned them ahead of time. After a few minutes I started thinking about the poor guy. He wasn't bad looking for his age, 45, and was well dressed, had a nice car and successful in his career. Charlie works as an IT consultant for a local firm that sends him out to various clients in the Midwest. I started asking myself what if? What if I went? Just one trip if he promised not to tell anyone? No one would believe him. As long as there was no sex what's the harm? Right? HMMMMMM?
Two hours later he came over again, chatting and flirting with me. Then he said he was making a business trip to Kansas City and said I should go with him. I asked if it would be two rooms or one room. The usual answer was one room! I asked if it was somewhere nice and he said Kansas City and we both laughed! After the laughter I whispered in his ear, 'Only if you don't tell'. His eyes almost popped out! He happily agreed. He had to promise me not to tell anyone, have two beds, he pays for all meals, and he has to take me to the Plaza for shopping, and no sex. Of course he agreed. He was to pick me up at my apartment on Wednesday night.
After that night I was so horny that I must have masturbated four times before the day finally arrived. We got in to Charlie's car and off we went. The trip was uneventful and we checked in to our hotel. It was now eight at night. We checked in and headed for the restaurant for something to eat. I reminded Charlie that nothing would happen and I was serious. Charlie was very polite and a gentleman the whole night.
In the morning Charlie went to work at 7:00am and said he would be back at 2:00pm. This gave me the chance to masturbate in the hotel room freely in the open air, legs spread apart. I brought along my purple vibrator and off I went. I was bent over with my face side ways on the pillow with my ass in the air with just a t-shirt on. If only Charlie could see me now! Afterwards I got some breakfast and later headed for the pool. When I got back to the hotel room Charlie was sitting on his bed eating a burger. He whistled as I walk in the room and I threw my towel at him and laughed. I sat on my bed Indian style with my bottle of water and we chatted on what our plans were for tonight. I started to get really horny just sitting there in my bikini. I knew Charlie was enjoying the sight and must be feeling the same way. I yawned to give him a full view of my chest. Then I propped the two pillows against the headboard and started to watch TV. However, I intentionally tucked my right leg under my left leg as my left leg lay straight. Giving him an open view of my crotch. He didn't know it but I was getting so wet. I wanted to touch myself right there. He finally got up and took a shower. I couldn't help but touch myself and climax before he got out of the shower.
It was my turn to take a shower. Afterwards I walked out with just the towel wrapped around me. I thought Charlie was going to have a heart attack. I started to get my clothes, bending over to give him a little peek here and there. I turned round and caught him looking at me and asked what he wanted to do. He could barely speak. I grabbed my clothes and put them on in the bathroom.
Charlie took me to the Plaza to do some shopping. We eventually got some dinner and went back to the hotel. At around 8:00pm I was exhausted and told Charlie I was going up to the room. He decided he would stay for a little while longer. When I got to the room I put on my favorite purple thong and lace bra. I jumped into bed waiting to see Charlie's reaction. I was horny and I started masturbating. I had my hand in my panties and was working away. I wasn't sure when Charlie would be back and I didn't care if he caught me like this. I grabbed my purple vibrator and had a huge orgasm. I fell asleep.
Later that night I woke up to a familiar sound. It was pitch black. But it came from Charlie's bed. Charlie must have seen me in my lingerie and I could hear him masturbating under his sheet. I turned to face him. It was dark and you couldn't see our faces but you could make out the shadows and the outline. All of a sudden he throws his blanket aside and I could see him masturbating his huge cock! I was so turned on! I started masturbating quietly. I could tell from his shadow that he turned to face me. My pussy was wet and I could feel my juices running down my fingers and ass crack. He has to know by now what I am doing. Finally I said fuck it! I throw my sheet aside and started masturbating like crazy! I had my eyes closed and started to moan lightly. Then I heard a click and opened my eyes. Charlie had turned his lamp on with one hand still on his dick. He started to walk towards me and I closed my eyes ready for a huge orgasm when I felt movement on the bed. I opened my eyes and held my index finger up and said no! He said OK and started to pump his cock while standing beside my bed. I started to pinch my nipples and I was about to cum when Charlie shot his load on my face and boobs. It caught me by surprise because he was standing by my belly button. I unintentionally licked my lips and caught the taste of his cum. I wiped my face with my right hand, placed it on my clit and I had a huge orgasm. I bucked so hard the headboard hit the wall a couple times.
Charlie was sitting on a chair close by. He was admiring every bit of my body. I tried covering up but he pleaded with me not to. I lay in front of him in my dirty lingerie. I took my hand and gave a pat to left side of the bed. He turned the light off and laid with me. He said thank you and gave me kiss on the forehead. I told him that was as far as it would go and not to try anything. I was embarrassed and he could tell. It felt good to be held. We chatted and replayed the situation. I noticed his dick getting hard as it started to poke my ass while we spooned. I wiggled slightly teasing it near my wet pussy. I turned round and jacked him off until he came.
The nest morning Charlie went to work and he got back around 5:30pm. We got a bite to eat and headed back to the hotel to watch a pay per view. I got in my pyjama pants and a football jersey. A total 180 from the night before. I could see the disappointment. I jumped on his bed and threw the covers over myself. We started to watch pay per view. I had my legs pulled up to my chest sitting with the covers over me watching the movie. While watching the movie I would play with myself under the covers. Not enough for Charlie to notice, We talked while I masturbated and he didn't even know it. Charlie took off his clothes accept his boxers. He went to the restroom to brush his teeth. I took advantage of the moment and took my pyjamas off and threw them across the room. I had my back against the headboard and knees up. I put the covers back on and started masturbating. Suddenly Charlie came out of the bathroom and laid next to me. We stayed like this for 45 minutes chatting and watching the movie. While I slowly circled my clit and occasionally sticking my finger in my ass and pussy.
Now when I get wet I get wet. I don't squirt but it does get wet enough that I will drip a lot of moisture. It feels good to feel my juices run down my ass crack and when it reached my ass hole I gasped! Trying to hold back from climaxing and losing control. Charlie looked over at me and asked if I was feeling OK. With a look on my face I whimpered 'no'. He looked at me and with a concerned voice asked if I was going to cry. I told him I wasn't feeling well. He said he would get me a glass of ice cold water. When he started to come back he noticed my pyjamas on the other side of the room. I was frantically circling my clit and with my other hand had a finger in my ass. I am so close to cumming! As soon as he looked at me I rolled my eyes back and I leaned my head back to the headboard and my mouth was wide open. I let out a moan and started to buck my hips. He pulled the covers off to see my wet naked bald pussy and I came so hard! He grabbed my left tit while I was still wearing my jersey and I squealed. It was the greatest orgasm. All I could say to him was 'go big red?'
Charlie started to masturbate and he touched my leg with his free hand. I just sat there and watched him. I love watching men masturbate. He started to get closer to my pussy and started squeezing the inside of my leg. I started to pinch and play with my tits. Suddenly I felt his finger on my clit and he started fingering me. It felt so good. I wanted to make him cum. After five minutes Charlie started bucking and spurting all over his chest and on the inside of my legs. When Charlie cums it's like a volcano! He bucked and I ground. I collapsed on his chest and could feel the cum between us. He started to get up. I held him down and asked where he was going. He wanted to get a towel but I told him no. I want the both of us to just lay here all night in our own dirty mess until morning. We did and we fell asleep.
I haven't seen him in years.