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In the interveining months since the start of our affair, Jake and I tried to sneak off together as often as possible and not to arouse the suspicion of my ex-wife. Most of the time it was a quickie before me went to school.
In the warmer weather the forest provided a wonderful rendevous location. There was a spot where there was cluster of Appleblossom tree. We’d lay beneath it and fuck as the white petals where blown off their branches and stuck to our perspiring bodies. Jake clutched the rough tree trunk as I drove my cock deep up his ass.
The colder weather were tougher to find secluded spots to get together but we manaaged.
Jake was becoming strikingly more feminine. His hair was now should length and his body movements were more girlish, even refering to his prick as his “clitoris”. I got a phone call from his mother informing me that she had caught “my son” prancing around in his bedroom in full drag. He had borrowed clothes from her and was even wearing make up. My head spun when I heard this. It should have come as no great surprise and that he’d evolve to this next level. I was told by his mother to have a talk with him.
When I picked Jake up he threw himself into the car with his arms crossed sternly over his chest. When we were a good distance away I reached out and stroked his cheek.
“That bitch!” he shouted.
I was somewhat taken aback by this outburst. Jake was not one for such hostility. He was usually a very calm and sedate boy.
He looked over at me with tears swelling in his eye.
“She ruined my surprise,” he said. “I wanted to surprise you. I looked really pretty.”
“I’ll bet you did,” I said, continuing to stroke his cheek. I had prominent erection in my pants. I divided attention between Jake and driving. I could tell he was quite upset about the whole matter.
I had decided to alter our destination and left it to be a surprise for Jake who continued to brood for a long while and remained silent despite my efforts to allay his anger. I reached out and rubbed his crotch. Despite his anger he got an erection which fondled through the material of his sweat pants. I tried to menatally imagine him in drag, but these thoughts were not condusive to safe driving and tried to temporarily purge them from my mind.
But before we arrived at our destination we made some business to attend to. I pulled off onto a secluded highway rest stop. Once parked I leaned over and gave Jake a long hard kiss. His mouth opened and gladdly accepted my tongue. We got out of the car and headed for the men’s room they had provided there. I’d taken the tube of lube I kept in the glove compartment and slipped it into my pocket. We were the only people there which put us at our ease. I put my arm around Jake.
Once in the men’s room, Jake had a little surprise. From out of his own pocket he removed a tube of lipstick. He turned to the mirror and applied it.
“I’ve practicing,” he said.
He turned to face me. His lips were a vivid shad of red. With the make up on his mood brightened considerably. We slipped into one of the stalls. The overall stench of the place was sickening, but we transcended the less than romantic location. We were together for a brief time.
Jake tugged my pants down around my knees and took my cock into his mouth with one starved gulp and his nose was buried in my pubic hair. He had become surprisingly adept at deep throating as well. His sexual education progressing rapidly and was an eager student.
I did not want to come in his mouth and pushed him gently away. He looked somewhat disappointed that I had cut the oral sex so short, but we other things to do today. I sat precariously and uneasily on the edge of the toilet and slipped Jaked’s sweat pants down and spread apart his firm white buttocks cheeks. For a few moments I stared contemplatively at that lovely asshole as it relaxed and tightend in anticipation. I opened the tube of lube and applied a generous amount on his asshole and my own lipstick smeared cock.
Given the confines of the toilet stall and my own position I was more less a passive participant. Jake settled back and slowly lowered himself onto my cock. I held it by the base and kept it steady. We’d fucked this way before so Jake knew what he was doing. I watched my cock slowly disappearing up into the depth of his rectum. He cletched the muscles and caressed me in the most appealing way. I brushed away his hair and kissed the back of his neck, tickling the nape with the tip of my tongue.
When I was completely in Jake settled down on my lap for a few moments to savor the sensations and suddenly just start to ride me as I passively sat there and watched. I reached around and was stroking his “clitoris”. Usually I carefully measured my strokes but we did not have a lot of time. If his mother were to call my apartment and we were not there it could plant some seed of suspicion in her mind. This was a secret that had to be carefully maintained. If we jerked off on our web cams it was only late at night after he was sure she had gone to bed and she would walk in on him pulling his pud in front of his laptop.
I tugged on his cock with ever quickening jerks until finally I spied a stream of come jet from the tip and strike the metal door of the toilet stall. He uttered a soft sigh.
I held onto his hips and assisted the excelleration of his thrusts. I was on the brink of an orgasm that has been pent up nearly a week since we last saw one another. Jerking off online was not much of an alternative to the physical contact of flesh—the sounds and scents which made masturbation empty and satisfying on the most superficial level.
I let out a long deep cry and felt the wonderful gushng sensation. I immediately wadded up toilet tissue to staunch the flow of sperm pouring out of Jake’s asshole and leave very tell tale stains on his pants. I simultaneously cleaned myself up. Within a matter of minutes we had cleaned up, composed ourselves, and were heading for the car.
It was not long before Jake realized that we were heading directly to my apartment. When we pulled into the parking lot of Target he shot he a radiant smile and seemed to be a step ahead of me. I confirmed his suspicion. The next half hour or so we spent buying a new wardrobe for Jake which would be kept at my apartment and he could wear freely whenever he wished.
He was floating on air when he picked out a couple bras and panties and seemed to be in his own world and seemed unconcerned if anyone witnessed this boy buying all these girls’ clothes. We went to the make up counter and he bought all that he wanted. He’d done a considerable amount of research online and with his mother’s cosmetics–a lot of trial and error, but was becoming more comfortable with the process.
Returning to my apartment our time was tight and I had to return him to his mother. We dropped all the clothes off at my apartment, which saddened him a bit, but our weekend together was coming up soon so he had something to look forward to. He promised not to wear his mother’s clothes anymore and freak her out.
I gave him a long hug and a kiss just before he got out of the car and I watched him as he walked up to the front door and disappeared.
I was glad that I could make him so happy.

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