George had been our neighbor forever. He was about 7 or 8 years older than me. I always thought he was a little gay, but he was always nice, and I never felt uncomfortable around him.
He had helped me with bikes and mowing the lawn and other stuff when I was a kid, since there was just mom and me. I always helped out with the house work and learned to be a pretty good cook. She said she always wanted a girl, also, but her and dad split up just after I was born, so there were stories she had dressed me like a girl for years, but I didn’t really remember any of that. I could have passed though, I’d always been teased as being to ‘pretty,’ and as much as I tried to work out, I could never get big and bulky muscles.

Anyway, after spending 3 years in college, I returned home to visit mom and celebrate my 21st birthday.
She had some of her friends over and a couple of my high school buddy’s showed up too. After everyone had left, I asked mom about George next door. He had started a collection agency and moved away downtown to a big nice condo and was doing fine. She said it was funny I’d ask, he had left a number in case I wanted to look him up when I came back to town. I was glad to hear that and without any thought of it, I picked up the phone and gave him a ring.

My car was a little, well lets say less than reliable, it barley made the 200 mile trip home, so George offered to pick me up the next day and we would hang out. He said he had a birthday gift for me, too.
We went into town for lunch, drank a few beers, since I was old enough to have one in a bar, and then he wanted to show me his condo. He had a great view of the city and the place inside was terrific. A big gourmet kitchen, big flat screen TV, and stereo stuff I couldn’t afford. We had a few more beers then he gave me my gift. It was an old photo album from when I was a boy, and he had me look all the way through it before I could say a word. Yea, there I was, from a baby until I was about 12 or 13, all dressed in girls pink frilly clothes. Tights, hats, dresses and cute little tops. I was adorable. George said he snatched the album so mom couldn’t embarrass me any more. She used to show it to all her friends as they drank wine, and they would laugh at the cute little boy.

Then George asked if I would do him a little favor, for saving the album from my mom and her friends. He took out a clothing box all wrapped in red and pink ribbons. Inside was a little girls outfit, but in my size. The pink tights, pink training bra and panties, a bright pink skirt and a tight little white ballerina ruffled shirt. “I always liked the album, too,” he said. Before I could say “hugh?,” he lifted me up from my chair and said he would help me get them on. I was boosted up, and as he walked me into the bathroom my regular clothes seemed to fall off everywhere. “Just relax, you’ll be fine, you don’t want those pictures getting out again, do you?”In the shower he soaped me up and shaved off all my body hair… all of it. He was naked too, and I couldn’t help but glance down at his growing cock. By the time I was all shaved, he had a full on hard on, and I was getting a little nervous. Still in a bit of a drunken haze, he dried us off and he put on a pair of sweats and a T-shirt. Now in his bedroom, I was dressed up in the girls outfit. All silky and snug in the tight pink tights, like pantyhose. The training bra was padded with little b cup rubber falcies, it looked like I had little titties, too.

I stood up and looked at myself in the mirror, Wow, what a picture. I was 13 again, and enjoying the soft silky feel of the tight clothes all over my body. I felt George behind me and he slipped a short blonde wig over my still damp hair. He positioned it just right on my head, then stepped back, and we both admired how cute I was. He sat in the bedroom chair and asked if I would walk around the room for him. He took some digital pictures, and I paraded around like a runway model for him. The tight pink cotton panties felt so nice squeezing my little package, and the tights slipping around my crotch with each step were moving them around a little. The cute little boobs would bounce a bit with each step. My cock began to grow just walking around the room, it was kind of cool.

George wanted some close up pictures, so I sat on the bed and he used some teen makeup, a little red highlight, and some glossy glitter lipstick that tasted like peaches. He was sitting on the bed right next to me, holding my head, and I could feel his breath on my face as he carefully made me up. After a few close up photos, he brushed my hair back from my face and held my head in both of his strong, gentle hands.
“I’ve wanted this ever since I met you, I’ve waited for this chance for years, and now you’re here. Don’t go back to school this year, stay here and let me take care of you. Like this, like a young man takes care of a young woman. OK?

I started to say something, but he leaned forward and pulled my face into his, kissing my open mouth, his tongue deep in my mouth. The sweet candy flavor of the lipstick was all around in our warm, wet mouths. He wrapped his arm around me and hugged me close as he continued to kiss and caress me. We hesitated for a breath, and I looked him in the eyes. My heart and mind were racing. I didn’t know what to do next. I wasn’t any good at romance. And this was even more foreign to me. I had a split second, say stop, or go on?

My instincts said to leave, leave the huge kitchen in the nice home, TV’s, stereos, and who knows what else? And what about the pictures he took today, and the ones he still had from before? What was to become of them? What was to become of me? Here I was in girl’s nylons and underwear? I was so confused. He was so nice and polite, holding me tenderly. What to do?
I told him I would stay, but just for a while, a few weeks perhaps, maybe longer.

I opened my mouth for him again and fell back onto the bed, and into his strong arms, kissing him more passionately than before. He moved his strong hands up on my perky breasts, fondling them like they were real. Pushing his long tongue deeper in my mouth, down into my throat, rolling half way up onto me. His leg moves up between mine. I feel like a high school girl on in her parent’s room, making out with a study buddy. “I’m going to give you your REAL birthday gift” he announces. George slides down between my legs and pulls the tights and panties down to my knees. My little hard on pops up but is immediately gulped up in Georges mouth. He sucks and strokes me until I can’t stand it anymore, I groan as I cum deep in his mouth. He swallows, then he licks my bare cock and shaved balls clean of my warm cum. Back up come the panties and tights. Snug up around my happy crotch. “Can you get me a beer, please.” He asks. I feel him admiring me as I walk out of the room and then return with a cold beer. He comments again on how nice look in the clothes, and how good I feel, and how he enjoyed tasting my cock, and my cum. He slowly drinks the beer, as I sit there next to him on the bed, my thigh being rubbed by his hand.

George never demanded I suck his cock, or let him fuck me. But after a few days of dressing up pretty for him, and him giving me blowjobs 2 or 3 times a day, I felt like I owed it to him. Sucking a guy’s dick was never anything I thought I’d ever do. But I never thought I’d have a guy suck mine, either. Or that I’d ever dress up like a schoolgirl, and model in the clothes while I was photographed. George was very happy when I told him I was going to give it a try, so he gave me a long, fat pink rubber dildo to practice on. I dressed up pretty in a dark blue skirt and sheer white blouse, so the black bra I had on underneath would show through. Pink silk thong back panties, of course, and some grey thigh highs. I’d bought a short black wig to complete the look. I wanted to look like the school library’s student aid.

I knelt by the bed and began to suck down the long rubber cock. In and out, squeezing it hard, stroking it, like George had done for me. He took some short videos, and lots of pictures while I practiced on it. He walked around and took shots of my various body parts. He really liked the sheer blouse and the look of the bra under it. I bent over as I sucked so he could photograph my cute ass and panties up under my skirt. I unbuttoned the blouse one button at a time, so to slowly expose the pretty black satin bra, I sucked on the rubber cock and he took pictures.

After an hour of this foreplay George couldn’t hold it any longer. I had gotten him really hot. He finally dropped his pants and walked toward me with his huge hard on bobbing around in the room. I opened my mouth and let the long rubber cock fall out, and replaced it with George’s bigger, longer real one. The taste was what really got me first. Warm and sweaty. I grabbed it to keep him from choking me in my throat, I felt it pulsating with anticipation of letting the big load inside out. I sucked hard on the top 4 or 5 inches, and squeezed the lower part, and stroked it, and squeezed it, and stroked it. George had taken mine all the way down his throat, but I soon realized how difficult that was. I tried, and gagged, and tried, and choked, and tried… and he came just then, spurting deep down my throat, just as I was trying to get a breath. I gasped and choked, my nose and mouth filled with cum. I spit some out my nose, and the rest came up out of my mouth, all over my hand, my top and my bra. I gasped again for air and struggled until I finally could get a deep one. I felt George’s hand on the back of my head…
“Eat it all up, sweetie, take your time. That was great, now finish it.” I looked to the side for a moment to see if I could see his face. But instead, I got a camera flash in my eyes. Later he showed me the picture of my face covered in cum, drooling and dripping everywhere. My clothes were stained from the wet cum, and my mouth was open letting more run out. I showered with him still wearing the school girl outfit, and he had me suck him off again there. I practiced on the dildo every day, and on George’s real cock a lot. After a while I got really good at dressing sexy, doing makeup and sucking and swallowing George’s cock and load. He lets me use the kitchen and everything in the house as if it were all mine. I haven’t registered for school again this semester, but there is always next year.