On the Job Training

In 1987, I was hired by a major retailer as a management trainee. As part of the hiring process, a group of us had to agree to go out of town for 8 weeks for training at an established store. We were put up in a local motel in Miami and were able to go home on the weekends. The days were very busy as we were trained in all facets of this company. There were about 20 trainees from all over the state that ended up here. We were assigned to share rooms. Nice motel and all expenses paid. It was a great set-up for a 24 yr old. I was able to have a couple interesting sexual experiences during those 8 weeks of training. My assigned roomate was named Joshua. He was from a different town and our paths rarely crossed as he was assinged to a different store. Also, Josh was often AWOL from sleeping in the room. He enjoyed the bar scene and according to him, he had lots of one night stands. Some weeks, I would'n't see him for a couple days, or he would come by after training to take a shower and then leave. Anyway, Joshua was an interesting person. I am straight, and I'm sure he was, too. He would brag about his conquests - I was not into the bar scene, and actually liked having my own room- since he was rarely there. Joshua was a fascinating person to me - he was 21 yrs old- just out of college and very free w/ sex. I was inexperienced and eager to listen. Joshua was good-looking- he freely walked around the motel room naked- he was hung- he had to be 8 inches flaccid. (I am 8.5 inches erect and later would find out the bigger you are flaccid, the less the growth is when you're hard!) I couldn't help but wonder how big he was when hard. I didn't have to wait long to find out. Joshua was the first guy I'd met who trimmed his pubic hair- he was i perfect shape and I was amazed at how easily he walked around the room naked- and talked about sex. The 2nd week training, I was in bed watching HBO- he came in around 10 p.m. and took a shower- afterwards, walked naked to bed- a couple minutes later, as we were watching something on TV(I can't remember the movie, but a couple was having sex on screen- very tame- didn't show anything), Josh sat up and said, "man, I can't stand it- gotta get rid of this build up". Without another word, he came out of his covers and began jacking off. I was stunned. I tried not to look, but I was curious about his size and found it weirdly stimulating- After a few seconds, Josh said, " feel free to join in- its a natural thing,." I meekly said, "no," Joshua was probably only a little bigger than I was when erect. He was huge flaccid, but grew very little when erect. It was just the opposite of me- I am small flaccid, but large when erect. I remember wishing I had jacked off that night- I wanted to, but was embarrassed. Over the next few weeks, he jacked off a couple more times in front of me- finishing, then taking a shower, usually. I remember thinking if he asked me to participate with him again, I would. I was disappointed he didn't. The night came- we were both in bed- one of the few nights he actually was there and he "whipped it out again". Josh started jacking and he said, "Don't you ever have to jerk? I don't know how you can stand it!" I said, "I'm ok." Josh said something like, "Come on, man, don't you want to jerk." Again, I meekly said, "no" , hoping he would try to talk me into it. Josh said, "man, it feels good- just do it. " That was my cue and I took it. I said, "I don't know... " Josh again encouraged me. I slowly took off my covers. I was in tee shirt and boxers. I had a hard-on that was straining. I quickly pushed down my boxers and began jacking like it was a race. Joshua seemed to ignore me and we both did our thing. It as a big move for me to jack off in front of another guy. Especially since we were both straight. He came first, I was quickly behind him. We both cleaned up and went to bed. I thought, I guess it isn't a big deal to jerk off in front of another person. I did it with him 2-3 more tims during the training. It felt weird each time, but it was a great release. Josh did comment to me once that I was pretty big, which means he must have beenwatching me a little, as I was watching him. A second sexual encounter I had during the training was much better- with a girl and a shower! All the trainees became good friends since we were all alone in Miami and had work in common. I met one trainee named Kaylee. She as 21- also out of college and lived a rather sheltered lif, much like myself. This was her first job following graduation and first time being away from home. Kaylee spent the weekends with her parents about 200 miles north of Miami. We instantly became friends- she was interesting and we had lots in common. The best thing about her was her sense of humor. I didn't hink of her sexually, really, but she was a pretty girl- nice figure and beautiful eyes! About the 5th week of training, Kaylee and I had developed a good friendship -very platonic. We ate out at night- sometime alone- sometimes w/ a group. We would often go back to my room and watch Tv. (She didn't like her roomate and Josh was usually gone.) I had a great time with her. To make a long story, not so long, one night we were watching HBO and they were playing "Hotel New Hampshire" with Rob Lowe and Jodie Foster. Granted, a crazy movie, but the sexual overtones were obvious- the oral sex Lowe received and sexual thoughts with Jodie's character. I had a hard-on during most of the movie- As usual, we were both laying on my bed. When my hard-on got too bad, I turned over on my stomach. Towards the end of the movie when Lowe's character takes a shower and runs into Foster's room to have sex, Kaylee blurted out, "What is your sexual fantasy?" I was taken back and stammered, "I don't know." Kaylee proceeded to tell me hers- I remember it was tame- on the beach, w/ picnic lunch and watching the sun set. (She didn't mention sex at all- romantic, but a bit boring to me). I thought some and told her mine was taking a shower- like Lowe's character in the movie, but with a girl. I had never taken a shower w/ a girl and thought it would be fun. Kaylee sat there for a minute- my erection is taking over my body, I thought. She left soon afterwards, and I jacked off- couldn't wait. A couple days later, we got off our jobs early and came back to the motel- it was Fri. afternoon, and we would be leaving for the weekend. Kaylee said, "I will come by a see you before I leave." She came by and I was packing- what a chose to pack up and leave each Fri. and go home, just to return on Monday. I was almost packed, when Kaylee knocked. She came in w/ a grocery bag. Kaylee said, "my roomate is taking a shower- can I use yours?" Then she smiled. I knew what she was hinting at. I said, "Kaylee, you don't have to do this." I had mentioned my fantasy to her in passing, every chance I got, and now she was going to participate! Kaylee said, "give me a minute and come in and join me.," Kaylee walked into the bathroom, shut the door. The shower began to run. I thought to myself, "What in the world are we going to do? How long should I wait to go in? I had an erection and wondered- is this platonic. If so, what will she do if she sees me hard?" I stripped to my boxers and went in- thinking, maybe my erection will go down. The bathroom was steamy and Kaylee was there- shower curtain closed. I said, "I'm here." Kaylee: "Come on in- its warm." I stood there- Kaylee opened the shower curtain- "Come on." She was defintitely looking me over- smiling. I couldn't see her yet. I thought, "Oh man, nothing I can do about this hard-on." I was embarrassed but thought, "Surely she means something sexual!". I dropped my boxers and jumped in. My eyes got a feast. Kaylee was gorgeous. I forgot about my own concerns about my hard-on. It got harder, I know, because she was beautiful. Her breasts were small- perfect- she shaved pussy into a nice little landing strip. I couldn't think. Kaylee looked at me - I could see her eyes traveling down and wondered aht she would say - She didn't say anything. Kaylee got out a tube of shower gel- "Is this part of your fantasy?, she asked. I took the gel and began soaping her up- my fantasy was coming true! I soaped around her breasts, careful not to touch. She led my hands in a circular pattern around her nipples- her nipples sprang into action. I got more brace and continued. While I was doing this, she began soaping me- my chest, mostly. I then ventured down to her vagina area. I soaped her all around her ass and inner thigh. I was ready to explode and told her she excited me. "I can see that,", she responded. Kaylee pushed me back in the tub by the drain and began soaping me- first the chest again and worked her way down to my butt and then bent down to my penis. It was swaying in the water and she soaped my balls in her hands- ever so gently and took my penis in her hands and soaped. I told her to stop, as I was cumming fast. Kaylee and I rinsed off- and I was a bit brazen and said, "Wanna finish" She didn't say anything- she led me by the hand-out of the tub- put on a towel- I grabbed one for myself and we fell on the bed. Just like in the movie, Kaylee grabbed me under the towel and said the same thing Foster's character did to Lowe, "Your balls are wet." She took off my towel and began pumping. I told her, "let me do you first." (I have more interest if I finish second!). I took her towel off and rubbed her breasts- then her clit- she moaned and came quickly- I was surprized. She kissed me lightly and then resumed her work on me. She had hands like silk- she pumped me a few times and I came quickly too. Kaylee commented, "wow, look at what came out!". I told her-"It is you- you did it to me!? We cleaned up. The next week, we did it again- we masturbated together. The final week, we did it one more time- this time in the shower, again. Kaylee was a wonderful diversion to a boring training for a new job. Both she and Josh helped me get rid of the sexual frustrations while away from home!