I had just returned from a trip and was getting ready to go out again when my partner called me into his office and told me we had landed a major contract in New York, it would take 6 months and the client wanted me to manage the project on site. The bad news was that I would have to move there for the duration of the project. Actually, I was excited at the prospect of moving to New York for 6 months.
As soon as I got back to my office I called Gwen, my best friend who lives in New York to tell her the good news.
"Oh Honey," she said, "That's great except I have bad news. I have to go to Europe for three months on a fashion shoot and tour. But I have a great idea. Instead of staying in a hotel, stay at my apartment. I have a huge extra bedroom you can use. Mrs. Abernathy, my maid comes in 6 days a week to clean up and cook so it'll be just like living in a hotel but with all the comforts of home."
"That's tempting," I told her, "but won't it be a bother to keep Mrs. Abernathy just for me?"
"There is one tiny hitch," she said, "my son Johnny is still at home."
"Didn't he start college this fall?"
"Actually he graduated high school at 15 is now a college junior at 18, studying business. I didn't want him moving away so young so he goes to college in the city. He's very bright but extremely shy. He won't be a bother and I would really sleep better knowing someone would be staying with him while I'm away."
"OK," I agreed, not really knowing what I was letting myself into.
A week later I was in New York, knocking on Gwen's door. She gave me a big hug, introduced me to Jonny who could barely look me in the eye and gave me the tour. It was a beautiful, spacious apartment. She saved my room for last. It was gorgeous, a huge queen size bed, a French Provincial desk with a computer, a bath with a whirlpool tub and a huge walk in closet.
It was like living in a hotel. The only time I saw Johnny was at dinner. When he learned what I did for a living, he asked if I would help him with assignments if he needed help. He was very bright and the problems he brought me were always complex challenges and I enjoyed the challenge.
I was enjoying living in the city. I loved the work and the nightlife.
I was out one Saturday evening, attending a corporate event and it was late when I got home. I quietly opened the door and let myself in. The apartment was dark and silent. I tip toed down the corridor to my room when I noticed a light shining from Gwen's door. I peeked in, expecting to see Gwen home for the weekend. What I saw shocked me!
The drawers of her dresser were pulled open. Bras, panties, stockings, slips, chemises, satin PJs, garter belts, and baby dolls of every color and style were scattered everywhere. Standing in the middle, wearing a satin robe was Johnny. He had a red satin bra in one hand, holding it to his chest and a pair of matching panties in the other. Sticking out of the robe was a huge, hard gorgeous cock. I couldn't believe my eyes as I took it all in. Suddenly he took the bra, wrapped it around his cock and began to slide it between the satin cups. The look on his face was ecstasy as he pumped slowly then faster and faster. The sight of that cock pumping in and out of that red satin bra started to really turn me on and I felt myself getting wet. He pumped and pumped until he stiffened and finally came, catching streams of cum with the panties until he was drained, then collapsing on the bed.
I didn't know what to do. I quietly stepped back toward my room when a heel accidently clicked on the floor. I quickly tip toed to my room, went in and closed the door. The sight of that cock, pumping in and out of that red bra had really turned me on. As I walked to my bed, I unzipped my dress and walked out of it. I reached into my drawer, pulled out my two favorite toys; a small vibrator that drives my clit crazy and a 7 inch vibrating dildo that drives my pussy crazy, my magic wands. I lay out on the bed, pulled my panties aside and spread my legs. I licked the small vibrator, turned it on and started to massage my clit. The sensations of pleasure were indescribable as I swirled it around and around. I could feel an orgasm building but I needed more. I took the vibrating dildo, turned it on and gently inserted it in my wet pussy lips as I continued to massage my clit. I pushed in slowly, inch by inch feeling it fill me and feeling the sensations of it vibrating. I started to pump, in and out faster and faster, harder and harder, massaging my clit. Faster and faster, around and around, the sensations electrifying every pore in my body when I started to shudder and shudder, experiencing an earth moving orgasm.
I lay on the bed, still in my bra, panties, stocking, garter belt and heels and as I tried to catch my breath I wondered how I was going to handle what I saw. I knew Johnny was extremely shy and lacked self confidence. I didn't want to embarrass him but on the other hand he had a lot of issues that needed attention. I got up, pulled on a robe and marched down the hall and knocked on his door.
"Come in" he stammered quietly.
He was sitting on his bed, dressed in shorts and a t shirt. I sat down beside him. He was quiet, very embarrassed and wouldn't look at me.
"I guess you saw me in Mom's room when you got home." He whispered.
"Do you want to talk about it?"
"Not Really"
"I really want to help you." I told him, "Help me understand. I won't tell your Mom."
I touched his arm gently and slowly and painfully the story came out.
When he was younger he discovered some of his mother's lingerie in the laundry hamper. He took it out. It was soft and smooth or lacy and it made him feel horny. He would try things on. His "thing" would get hard. When he massaged his "thing", it felt so good that he never wanted it to end. He would massage and rub until he came. Whenever he was frustrated, he would go to the laundry bin. He found the smell of the lingerie different but it always made him feel horny. He told me when his mother was away, he would go to her room, open her lingerie drawers and try on different things to make him horny and then he would rub himself until he came. He would wear lingerie in the house and even sleep in it because it felt so good. He found solace and comfort in his mother's lingerie.
He finished high school at a very young age, went to college and never had any friends his own age. The girls in school were always older that he was. They wanted "Johnny's" help in school but they thought him a smart little brother. He never went to his prom, never been on a date and had ever even kissed a girl.
