This happened about 35 years ago. I was staying at a Roadway Inn in San Diego with my parents during summer break. I had just turned 17 and really wanted to spend time with my friends, but my parents didn’t trust me alone in the house so I was forced to go with them. What made it even worse was that my dad was extremely cheap, and wouldn’t even spring for an extra bedroom! The tiny hotel room consisted of a queen size bed and a single cot to the side where I would be sleeping for the next five nights.
Anyway, it was mid afternoon and my parents had left me alone at the hotel to go visit my aunt. I had decided to feign illness because I just wanted some time to myself after the six hour car ride. About ten minutes after they left, there was a knock on the door. I opened it, and standing in the doorway was one of the most beautiful men I’d ever seen…before or since! At the time he seemed much older but in hindsight he was probably around 25 or 26. He said that he worked for the hotel, and that someone in our room had placed an order for a massage. I told him that it might have been one of my parents but I didn’t expect them back for at least a few hours. He flashed me a smile and said that since the massage was already paid for, would I like to have it? I nervously agreed and motioned him into the room.
I started to lay down on the cot but he stopped me and asked why I wasn’t laying on the larger bed. I explained to him that the cot was my bed, and the queen size bed was my parents’ bed, and the cot is where I slept. He laughed at that and told me to be adventurous. I asked him if I should take off my shirt, and he suggested I remove all my clothes as he didn’t want to get any massage oil on my shirt or pants. I stripped down and quickly laid face down on the bed to conceal my growing erection.
I nervously made small talk with him as he began gently massaging my back. I remember asking him how much he made giving massages and if his gig ever got him free pussy! He smiled and said that yeah, sometimes one thing could lead to another in his line of work. As he said that, I could feel his hands moving down my lower back, brushing past my bare ass cheeks, and placing a hold on my upper thigh. At that point I was completely hard as I felt his hands getting closer and closer to my dick.
Suddenly he stopped and instructed me to roll over on my back so he could massage my chest. I think I turned beet red and told him I couldn’t because I had a little problem “down there”. He laughed and told me he was used to it and not to worry. I slowly turned over to reveal my massage boner. Without hesitation he placed both hands on my cock and slowly began jacking me off. ‘Does this feel good?’ he asked. All I could do was nod my head in reply.
He then started simultaneously fingering my hole and the sensation was out of this world! I was so close to coming when he stopped and asked me - very politely too - if it would be okay for him to fuck me. I nodded my approval and at this point I would have refused him nothing. I remember it was painful at first but he was so gentle and every so often he would ask me if he needed to go slower.
When it was over, he kissed me on the forehead, got dressed and said he hoped we would run into other again someday. He didn’t leave his business card or even tell me his name.
My parents arrived back at the motel later that evening. They went straight to bed and I was already fast sleep in the cot, completely exhausted from my first sexual encounter. The mattress of their bed must have been covered in dried oil and cum, but they never said a word about it the next morning.