That evening he thought about Gene and what had happened in their old fort. He finally had the opportunity to wear something besides the slip he had shoplifted and really enjoyed dressing up for his friend and what had happened as a result. He didn't feel weird or strange about it.
"Maybe I should have been born a girl," Ian mused before falling asleep.
Two days later Gene appeared at his door with another paper bag. Inside was a pair of black silky nylons and a black silk and lace garter belt. Now Ian had no idea how to put the nylons on but then he recalled a picture on the cover of a trashy paperback of a woman sitting on her bed and donning nylons.
It took some doing before he figured out how to draw them up his legs and not tear them. As he attached them to the ribbons of the garter belt he was already hard. Gene, of course, was playing pool as he waited patiently for Ian to dress.
It was a whole new sensation he felt as he slid the panties up his nylon-clad legs. His arms were covered in goosebumps and his nipples were quite hard. He then added the black half-slip and placed the bra around his chest with the rolled-up socks filling out the empty cups.
Ian then placed the wig on his head and dug out an old mirror that he had rescued from the trash and hidden in the fort after our last session. This ensured that none of my dark hair was visible and would help me with my surprise for Gene.
My surprise was that I had purchased a tube of lipstick and some eyeshadow. I told the clerk that had appraised my purchase with a strange look, that I had spilled a can of pop and ruined my girlfriend's and now I owed her. Now Gene said he looked like a girl without makeup and Ian could only imagine his reaction to this surprise.
He used the mirror to apply them as I had seen them do in the movies. The effect was unbelievable and he looked as good as one of the pretty girls at school, even better. Once again his heart beat faster as he arranged himself on the pillows and called out to Gene.
A second later he saw and heard him enter the fort and his mouth hung open once his eyes adjusted to the dim light and he got a good look at his buddy.
"I don't believe it. You look even better than last time," he said as he began to strip off his clothes. He then laid his naked body next to his friend. The pretty girl then watched with unblinking eyes as he slowly hiked her slip up. Ian then turned on my side and threw a nylon-covered leg across his lower belly. Ian slid his free arm around his buddy's neck and cradled his head so his face was against his bra.
Ian then took hold of Gene's hard teenage prick and began to jack him off. This time it was Gene that moaned at the sensation of my nylon leg across him and the feeling of my silky bra against his face. I wondered if he could feel my hard cock in its silky cocoon pressed against his leg.
"You like that, baby?" Ian asked in that same soft voice that he had used last time.
"Oh, yeah. It feels so good," he responded as his hand began to run the length of my leg
It felt very good to feel Gene's warm and smooth hand rubbing Ian's nylon-clad leg and he increased the speed of his hand on Gene's cock. Now with all this new stimulation, it didn't take long until he was ready to shoot.
"I'm gonna cum," he announced.
"Then go ahead," Ian's soft female voice whispered into his ear as he removed his leg from across his body.
A second later I felt his body stiffen and his cock emptied its load on his stomach before he flopped on his back, I was still on my side watching the strands of cum slide down his belly. I managed to grab his underwear and wipe him clean. It was about a minute later that he turned on his side facing me and pushed me on my back.