That evening after Ian had crawled into bed and switched the light off he thought about what had happened in the fort that afternoon between him and Gene. As usual, Ian had dressed up all sexy for his buddy in the clothing that Gene had pilfered from the donation bag that his mom and sister had prepared, and he looked forward to an afternoon of deep tongue kisses and mutual masturbation.

Ian had taken his time with the makeup and the reflection in the mirror showed the face of a very pretty teenage girl and not that of a teenage male, the more he practiced the better-looking he became. He had called Gene before heading down to the fort and told him that the house was empty and he could come over any time he wanted. Ian went on to tell him that the door would be unlocked and he had to make sure that the door was locked behind him. Gene replied that he would drop the bag of clothing at the entrance of the fort.

Ian had a difficult time donning his lingerie as his own cock was hard and throbbing at the thought of what lay ahead for him. After what seemed like hours he heard Gene calling his name and telling him the clothing had arrived, Ian walked on his knees to the front of the fort to retrieve the bag.

His heart and cock jumped for joy at the sight of the contents of the bag. The silky mini skirt and blouse were a perfect fit as were the heels and Ian couldn't wait to don them. Once dressed he called out to Gene and a second later his buddy and lover were at his side where Ian began to remove his friend's pants and underwear in between gentle kisses.

Gene was already as stiff as steel and Ian commenced to slowly stroke his friend's erect cock but was stopped before he really got started. He was handed a bottle of baby oil with the request to use it lest he is rubbed raw.

Ian covered Gene's cock with the slippery substance and then returned to stroking it it seemed to heat up between his gentle touch and Gene's body heat, it was shortly afterward that everything changed, Gene suddenly left his friend's side and then maneuvered Ian's body until he was flat on his back.

"I dream about fucking you every night and I am tired of dreaming," Gene told his friend.

Gene's hands shot up under Ian's mini and the bikini panties were slowly slid down the nylon-clad legs of his friend. A second later Ian's skirt and slip were pushed to his just past his crotch and a heartbeat after that Gene's strong arms slipped under Ian's knees and lifted them until Ian's knees were pushing against his fake boobies.

The bottle of oil was in his hand and he squirted a healthy spray into Ian's butt. Then slowly he aimed his rock-hard cock toward Ian's virgin ass and pushed himself inside amid some of the sexist moans he had ever heard.

Now Ian could have stopped it as he was physically stronger than his friend, but he didn't want to stop him and allowed his friend to fuck his virgin ass. It was better than he expected and that was how it started. Now every weekend they got together in the cardboard fort.

School ended for the Summer and the two boys looked forward to seeing each other every day instead of just the weekends, it was recently that Ian noticed a change in his friend's attitude. He was still gentlemanly and very gentle with him, but there was no attempt to mount him more than once, Ian was convinced that Gene got what he wanted and was now bored with his new lover. Ian wondered if that's how those that were born female felt after giving their virgin pussy to their lover and then being mildly ignored.

Ian waited until the end of the first week of vacation and they were secure in the fort before Ian posed the question to Gene about his attitude, there was a long silence before Gene mumbled a response.

"When can I have a turn?" Gene asked in a strangled voice.

"A turn to do what?" Ian replied.

"To dress up all sexy like you," was his response.

Ian sighed in relief before answering.

"But you never said anything," Ian responded as he moved in to place his arms around his friend. "You always talked about being with a girl that dressed up all sexy for you."

"It only happened since we became close and I saw how pretty you looked wearing them and how your lingerie felt when you pressed them to my body and how stockings felt when I ran my hands over them. Do you know that I've raided my sister's room and made off with one of her sexist bra and panty combinations? I wear them whenever no one is home and jack off into them," Gene answered.

"Just bring some clothing over on your next visit and I'll do your makeup," Ian told his friend.

Now the boys had chores assigned by their respective parents which provided them with a generous allowance, but it didn't take all day if they hustled and it left plenty of time for get-togethers in the fort. Now on the weekends, there were no tasks and that made the weekends perfect for dressing up. Both Gene and Ian's parents were golf addicts and the weekends were for the links.

Saturday arrived and Ian's parents headed to the golf course, his grandma who was charged with taking care of his baby brother was taking him to the park and that would free up the entire afternoon. Ian tidied up his room in preparation for his friend's arrival and then got himself ready. His skill at making himself look female had increased a hundredfold and he looked better with each application.

Ian had picked up a wig at the second-hand store where he received no raised eyebrows at his selection along with a long-sleeved silky pink blouse, and that's how Gene found him when he arrived.

"Can we do it in the fort?" Gene shyly asked.

Of course, Ian responded. " Anywhere you want, it's just easier to do the makeup in here, now take a seat and lose that t-shirt.

Gene removed his shirt and sat on the edge of the bed. A second later Ian pulled two chairs up, one was laden with makeup and brushes. After taking a seat Ian commenced applying makeup to his friend's face, as he did this he felt his own cock begin to stir as his friend's masculine appearance began to fade, and was replaced by a feminine one. Gene was gorgeous with makeup and the addition of a wig made him even prettier than Ian was.

"OK," Ian said after a time. "The makeup is done, now you can change."

Grabbing the paper bag that he had carried Gene made a beeline for the master bath and when he emerge Ian thought his cock was going to tear through his panties. There stood his best buddy in a pink bra, panty, and garter belt combo that was trimmed with black fringe.

His friend also sported a pair of black thigh-high stockings. The combo appeared to be made of satin by their shimmer under the light. Gene was instructed to once again sit on the bed as Ian began to apply lip gloss, he notice that Gene's cock was very hard under the tiny shiny panties.

"Where did you find such a sexy outfit?" Ian asked.

"Buried in the bottom of my sister's lingerie drawer," his friend replied.

"You are beautiful," Ian said to his friend while planting a quick kiss on his cheek. "Now we can go to the fort."

"I've changed my mind," Gene stated.

"I thought that's what you wanted?" Ian asked.

"So did I, but now I think I prefer the bed. Are you OK with that?" Gene asked as he scooted himself toward the head of the bed.

"More than OK," Ian added as he mounted the bed and lay on his friend's side,

"Are you going to fuck me, pretty girl?" he asked.

"Yes, I am," Gene responded trying to sound feminine as possible.

Ian could see Gene's cock pushing against his shiny panties and it looked bigger than normal.

"Can we try something different?" Gene asked.

"What did you have in mind? Ian replied.

"Get on your hands and knees," Gene requested.

Ian complied and a second later Gene clambered around to position himself behind his friend. He then felt Gene's hands slide down his panties.

"I saw this in one of my dad's magazines and I imagine being on your back with your legs pressed to your chest made your breathing difficult."

"A little," Ian responded.

A heartbeat late Ian felt the sensation of the slick oil being squirted on his anus and he moaned with pleasure.

"Now lower your upper torso, "Gene commanded.

Ian complied.

"Now turn your head to the left and look toward your dresser, "Gene continued.

Ian did as requested and discovered why Gene didn't was to use the fort. The mirror of the dresser reflected the image of a very attractive teenage girl on her hands and knees and another attractive girl kneeling behind her.

He watched as Gene lowered his panties to just enough to allow his rock-hard cock to spring out and then taking his cock in one hand he directed it toward Ian's butt.

"Are you ready? Here it comes," Gene said in a soft whisper as he pushed himself inside his friend amid some of the sexiest moaning Ian had ever made.

The sensations of silk against silk and nylons brushing against other nylons were more than Gene could take and he lost his load very quickly. Gene grabbed the box of Kleenex and wiped off his cock before pulling his panties back up. Ian's orgasm ended and he took his place at Gene's side where they shared gentle kisses until Ian's cock began to tingle and thicken and it wasn't long until Ian's cock was ready for action.

"Are you ready?" he whispered in Gene's ear.

"More than ready," he responded as he took the hands and knees position.

Ian covered his friend's virgin ass with a generous coating of the slick oil, he then did the same to his hard cock.

A second later he had moved behind his friend and positioned his throbbing cock against Gene's anus.

"Just relax," Ian told his friend. "If it hurts too much I'll stop."

"Please fuck me," Gene managed to moan.

Ian then began to slowly push himself inside Gene's ass, Gene moaned with each passing second.

"I'm all the way in, pretty girl," Ian told his friend.

"It feels good," was all Gene said.

The dresser mirror reflected the erotic show on the bed and added to Ian's excitement, so much so that he finished faster than he expected to. Ian removed himself from Gene's ass and lay at his side where they shared gentle kisses and carcasses and wondered what more could the Summer bring.