Ian discovered at a young age that he had the desire to wear female clothing, but not just any clothing, it had to be silk and or satin. He thought maybe it was a phase that he was going through. He figured if I ignored these desires they would pass. Ignoring them didn’t work and they became more intense.
He often found himself sitting and staring at the lingerie section of the large Sears catalog with the same intensity as he once perused the toy section. The images on the slick pages of full and half slips, nylons, and garter belts along with the various wigs and nightgowns always got him as hard as a rock and he sat wishing he had some of them to try on.
Wishing was all one could do. This was the sixties and there was no internet so there was no online ordering. A young man attempting to purchase lingerie was sure to raise eyebrows.
Now his boyhood friend Gene also loved these same articles of clothing, except he had no desire to wear them. He wanted to lay with a girl that was clad in them. Now they weren’t bad-looking teens but were very shy around the girls at school. So Gene’s hopes were for naught. All they had was our desires, imaginations, and masturbation.
Ian remembered telling his buddy about the black half-slip and matching panties that he had recently shoplifted from a specialty shop when he was forced to accompany my Mom on a shopping trip.
“I wear them at night when I jerk off,” he confessed.
As Gene and he were sharing embarrassing secrets that afternoon, Gene disclosed the fact that he had rescued one of his sister’s silky nighties from the rag bag.
” I beat off into it almost every night,” he admitted.
“It was a good thing I don’t have a sister as a lot of her lingerie would be missing, ” I told him after his revelation.
Gene fixed me with a slight smile before continuing.
“So you’re saying that if I borrowed some of her things and brought them over you would wear them?” he asked in a trembling voice.
“Yes,” Ian responded in an excited voice.
“Would you let me see you wearing them?” Gene asked.
“Of course,” Ian responded.
Now Gene spent a lot of time at his house as he was the only male child in his family. They didn’t hang out with the neighborhood kids very often as they all wanted to play baseball or some other such sports. They preferred to read, watch television, and played board games. Sometimes Gene borrowed one of his Dad’s Playboy magazines and the teens devoured the pictures within.
Once Gene discovered that his Dad’s file cabinet was unlocked and he came across an 8mm porno film from his Father’s collection and brought it over. Ian would set up the old movie projector and they would watch the grainy frames of couples doing the down-and-dirty. Afterward, they would have great discussions about girls they wanted to perform those acts with.
Now in their childhood, they had built a fort in the corner of my basement from three old refrigerator boxes and it became a variety of housing for the characters when we played. Ian was even allowed to sleep in it one night as I had outfitted it with an old sleeping bag, blanket, and pillow.
When they outgrew the place, they didn’t throw it out but kept it together because Ian often hid there when he needed to be alone. I recalled it was shortly after school ended for the Spring break that my Mom called him to the phone one evening, his buddy was on the other end.
“I have something for you,” he said.
Ian’s teenage prick jumped as he spoke the words.
“What did you get?” I asked barely able to keep my voice low.
“You will have to wait and see for yourself. So when should I bring them over?” he asked.
“Tomorrow,” was all Ian said. “Mom’s going shopping and Grandma is babysitting so we can use the fort.”
The next day he flew to admit him when Ian saw him walking up the driveway with a shopping bag. He was met at the door and the bag was taken to our fort, he resisted the temptation to look inside. They lingered upstairs until Mom was getting ready to leave, she gave the speech about behaving and making enough noise to wake the baby.
As soon as Mom backed out of the driveway Gene and I headed downstairs. He occupied himself playing on the pool table while he entered the old fort. Once inside he could no longer stand upright, so Ian grabbed the bag and walked on his knees to the back of the fort. He emptied the contents of the bag and his hard prick almost tore through his jeans.
Inside were a blonde wig, white bra and panties, and a white silk and lace half slip. He flopped on his back and couldn’t remove his street clothes fast enough. As he slid the silky white panties up his legs, he could feel the tingling sensation in his cock and balls that heralded an erection.
Next came the white half-slip. he ran my fingers over the embroidered hem before he drew it up slowly to enjoy the sensation of the smooth and cool material caressing his legs. Ian was as hard as a rock before the elastic band settled on my waist.
He fastened the bra around my chest and felt sad that he could not fill the empty cups. To remedy this, he grabbed his socks and rolled them up, and inserted them into the empty cups. I ran my hands over my fake boobs and was pleased with the sensation. I then placed the wig on my head and made sure that none of my dark hair was exposed.
I laid back against the pillow and I was as ready as he would ever be, so he called out to Gene. A second or two later Gene’s figure was crawling toward me. Ian’s heart beat faster as he moved and soon Gene was kneeling at his feet. It wasn’t totally dark inside the box thanks to some small holes in the side and roof.
Ian could see him smile as he knelt there just staring at him.
Damn, if you don’t look like a real girl,” he stated.
“I want you,” Ian said in a feminine whisper that surprised even him.
It was a line we had read in a trashy novel and it seemed appropriate. A second later his buddy began to strip off his street clothes. I ran my hands over my lingerie-clad body and told him to hurry. Once again the request was made in a soft silky voice that he never knew he possessed. Soon my buddy was totally naked and sporting a tremendous hard-on.
Ian became excited and his prick stiffened in its silk prison. Now he expected Gene to grab his manhood and commence to jack off as he stared at me. So Ian was a little taken aback when he crawled forward and placed his knees on either side of my thighs. He lowered his body so that his cock was flat against his belly and slip.
Gene began to slide his manhood up and down against his friend, he wasn’t afraid, he was excited and he moaned. That seemed to excite Gene even more and he increased the speed of his sliding.
“I like it when you make that sound,” Gene confessed.
“Then I’ll keep doing it,” I responded.
Ian’s own cock had grown very hard in the silky panties and I could feel the heat of his hard cock against it as he slid up and down the slip.
“That feels so good,” I told him in that soft feminine voice.
That caused him to increase the speed of his slide as well as increase the weight of his body against me and I was in heaven. I was dressed in the silkiest lingerie and a long blonde wig while my buddy was rubbing his hard prick against me.
“I’m cumming,” Gene said after a short time and I told him that I was also ready to finish.
Less than a second or two later he emptied the contents of his balls on the slip while I let loose in my panties. Gene then collapsed on top of Ian and stayed there for about a minute, they both breathing hard. Gene eventually crawled off his friend and redressed. Ian waited until he left before I shed my finery and redressed.
I grabbed us a couple of bottles of pop and we headed to the patio.
“That was something else,” Gene finally said.
“Yes, it was,” Ian responded.
“Can we do it again?” he asked hopefully.
“Anytime you want,” Ian responded.
“Good. Then keep the wig and the other stuff,” he told me.
“Won’t they be missed?” I asked.
“Naw. My sister has dozens of panties, slips, and bras. The wig had long been forgotten about and was in a junk closet.” he informed him.
“How do I clean all the spunk off of them?” I asked.
“My sister washes them by hand in the sink with a bar of soap. She then hangs them up to dry.” I was told.
“I can hang them in the fort as no one goes in there but us,” Ian informed him.
“Maybe I can borrow a pair of her nylons and a garter belt for our next session,” Gene said with a smile.
“That would be great,” Ian responded as his prick began to thicken again at the thought of wearing nylons.
“You know if anyone finds out we’re screwed,” Gene added.
“Then we must keep this a secret,” Ian responded and we swore each other to silence.
To be continued.
