At 15yo I was living with foster parents. I didn't grown up with parents that would win any awards either. I was at the age that I wanted to drink and have sex, took after my parents I guess? I didn't have a girlfriend so I masturbated daily, sometimes two or three times a day.

My foster parents had me join a church youth group. At first I hated it, I wasn't into religion. God was talked about with my folks, usually the word "damn" followed the word God and a few other curse words as well.

Dale was the church youth leader, a single guy and I noticed all of the kids seemed to really like him a lot. We were a group of teenagers, all doing our own things. Most of the boys smoked, weed too. Drinking was something even most of the teen girls joined in. Now I found this out at Dale's house only a short time after joining the youth group.

I had been with the group about six months, Dale used to spend a bit more time with me since I didn't really have a family like the others did. I never gave it a thought when he would give me a hug or do something nice for me.

Dale had a birthday party for a kid named Greg, he turned 17yo and Dale had a party with beer and alcohol. Dale's thought was he wanted the kids to party at his house so they wouldn't be out drinking and driving. Most of us, including the girls got hammered. I was ripped and I needed to lay down. Dale said to lay down on his bed, most of the other beds, sofa's and chairs were occupied with drunk teenagers.

I had no idea what time it was when I opened my eyes, it was pitch dark outside. I lay there and suddenly I had this strange feeling between my legs. The first thing I noticed was the fact my cock was rock hard, the next thing I noticed was a hand rubbing my hard cock. I tried to sit up but my head was spinning like a top from the alcohol. I fell back on the pillow, I don't know if I spoke or not?

The hand kept rubbing, stroking, then a warmth surrounded my cock. It was warm and wet all the way to the base of my hard cock. I think I moaned, made some sound. Honestly I wasn't sure if it was a sound of pleasure or the pain of alcohol in my system. I lay there flat on my back, the pleasure between my legs intensified. I had masturbated many times, I knew the pleasure of doing myself, I didn't know the pleasure of someone else doing the same thing and more!

The pleasure became intense, I clawed the sheets next to me, trying to hold onto something as I felt that moment I knew I was about to cum. I arched my hips, my head seemed to ring like a bell as I felt my hard cock spasm. Whatever was happening to my cock wasn't stopping, I made some kind of moaning sound and ejaculated with intensity. I thrust my hips, shooting my cum and hearing a soft moan below my waist. Moments later I was done, that sensation of release had passed.

The sucking and licking sensation continued for a few more seconds, I lay there with my head pounding, I wanted to sit up and see what was going on, my stomach was also spinning, but in a bad way. There was movement below, like someone had got off the bed quickly. I just lay there wanting to die but there was a feeling of pleasure as well. Finally able to drift off to sleep, I woke up late the following morning.

My head still hurt but not quite and bad, my stomach was still not happy. I sat up slowly and sat in the bed. I could hear Dale's voice and some younger voices downstairs. I slid my legs slowly off the bed, looking down I saw dried white spots on the crotch of my jeans, the fly was unzipped.

I went to the bathroom and pulled out my cock to pee. My cock was sticky and my underwear was moist, I could smell a scent of cum. I cleaned up a bit and went downstairs to the kitchen. I saw Dale at the stove cooking something, my stomach was not up for food. Dale smiled and said hello when he saw me, just a quick glance, nothing out of the ordinary. I grabbed a soda from his fridge and my cigarettes, going outside to smoke.

I sat down at the patio table and lit my cigarette, my thoughts drifted between my upset stomach and what happened. Part of me enjoyed that feeling, no wonder my dad talked about a blow job could make anyone feel better. I didn't understand at the time but I did now, except for the fact that my first blow job came from Dale.

With many more parties and not having control of my alcohol intake, it wouldn't be the last time Dale would suck my cock to completion. A few months later I had a girlfriend, but she wasn't into blow jobs or having sex much. Her parents wanted her wait until she was married before having sex. I fingered her several times and then I would go back to my foster parents house and masturbate in my bedroom.

At some point Dale and I had a talk about what was going on between us. It was hard to admit I liked the feeling but I liked girls better. He smiled and said he understood but he also knew I needed to cum. Then he stood up, smiled at me, telling me not to worry, he would give me what I wanted.

For a while I stopped going to the church, Dale called a few times to see if I was okay. I was so confused. I hated what had happened, knowing it wasn't right. I would lay in my bed at night and think about what Dale did to me, my cock would twitch and I could feel it getting hard and then masturbate before I could sleep.

Greg and James came by the house one day, they talked me to going over to Dale's house. It was Christmas and everyone was going to be there. There was beer and alcohol as always but I didn't drink too much. We had food and gifts were exchanged. Everyone knew my home situation and a few of the girls gave me gifts.

It was getting late, the kids had to get back home, nobody was going to be sleeping over at Dale's that night. Dale asked me to help him out for a few minutes and when I came back out Greg had already left with his girlfriend. Dale said not to worry, he would take me home after he did a few more things. Dale went upstairs and I went into the tv room.

I was watching some Christmas show and without much excitement my eyes got heavy and I drifted off to sleep in the sofa chair. I had no idea how long I had been asleep when I felt someone moving my legs apart. I jumped and there was some older women on her knees between my legs smiling at me. I was more than surprised, then I was suddenly freaked out to realize it wasn't a real woman, it was Dale dressed as a woman.

I pulled back, trying to curl up in the chair. Dale put his gloved hands on me and told me I needed to relax. I could smell perfume of sorts suddenly. I looked at his Face hidden behind makeup, mascara, eye liner and lipstick. He wore a curly wig. He told me he would give me what I wanted. His gloved hand went to my crotch and started rubbing me. I closed my eyes and I just knew I was dreaming this. His hand pressed into my crotch harder, squeezing my cock and telling me it would be better this time.

Honestly I don't know how much I resisted, my mind wouldn't let me think. My body began to react to his manipulations. Dale kept whispering to me in some weird female tone of manner, it would be okay. Thinking now I need to go home, I didn't really want this but suddenly I felt that familiar tingle between my legs. My cock began to get hard, Dale could feel it happening as well.

He whispered it would be good, he would be the girlfriend I needed. His gloved hand rubbing my cock harder and I was trying to ignore the pleasure that I remembered so many times with my own hand. I just gave in and I don't know why. I allowed "her" to do what she wanted with my cock. She sucked and licked my cock with hunger, cupping my balls and telling me my cock was beautiful.

I could hear the sexual excitement in "her" voice. I opened my eyes for a moment and looked down. Her thick curly mane of hair blocked my view mostly, I looked behind and saw "she" was wearing high heels along with her stockings under her skirt. Her head bobbed up and down on my throbbing cock, I was very turned on by the feeling now.

Then Dale's mouth pulled away, she was gasping with excitement. I looked down at my cock, it was redish color from her lipstick. The sight of it just did something to me I never expected to happen. Dale stood up and reached down and took my hand, pulling me up as well. He led me upstairs to his bedroom, candles were lit around the bedroom.

Dale stripped me naked and lay me on the bed. She walked around the bed in those heels and knelt onto the bed close to my head. Dale reached down and stroked my cock that was still hard as stone. Then she brought her hand to the hem of her skirt, lifting it up so I could see underneath. Dale tucked her cock inside a pair of lace panties, she was hard as I was now, the head of her cock couldn't be contained inside the frilly lace material.

She pulled her cock out, stroking herself with her gloved hand. She looked upwards and moaned into the air. I couldn't help but look at her masturbate her own cock. She did this for a few moments and then looked down at me lying before her. Dale reached down and took my hand and placed it around his thick cock. The sensation was strange, his cock was warm and it throbbed in my hand.

Dale whispered for me to stroke his cock. I looked up into his female looking face. In the shadows there was a resemblance of him being a woman. I slowly tugged his cock, Dale moaned with pleasure instantly. I stroked his cock, he told me to do it faster, I did as he asked me to do.

Dale moaned like a girl as best as he could, his head tilted back slightly. I lay there looking at his hard cock beginning to drip pre cum. Then without a word from Dale I leaned over and took his cock into my mouth, I don't know why I did that. The first words to come from Dale's mouth was thank you, thank you!

The sensation of having a hard cock in my mouth was overwhelming. I don't know why but I wasn't repulsed by it one bit. My body tingled as his throbbing cock pushed into my mouth over and over. To hear that weird female voice aroused me in some unknown manner I cannot explain. I began to suck her cock with fever, taking the base of her seven inch cock and doing to her what she did to me in the darkness not so long ago.

She thanked me again, told me she loved me. I tried to take all of her cock when she told me that. I gagged I couldn't take it all, Dale looked down at me and smiled. She told me not to worry, I was so good she wasn't going to hold out much longer.

She pulled her cock away from me and began to jerk herself off. I watched her gloved hand fist herself, she leaned back slightly and cried out. A rope of cum jetted out of her engorged cock, and splattered all over my bare chest. Dale jerked her cock for several more moments until she was spent. I lay there on the bed with Dale's cum running down the sides of my chest, it felt almost hot on my bare chest.

When she was spent Dale looked down at me and began to apologize for what she had done. She slid off the bed and went to the bathroom, returning with a towel to clean me off. I lay there looking up at Dale as she wiped my chest clean of her cum. I said you make a wonderful girlfriend. Dale stopped and looked at me and smiled.

Dale walked over and put the towel into a laundry basket, she walked perfectly in those high heels she wore. From a short distance Dale could pass as a woman, she could be my girlfriend if that's what we wanted. Dale slid into the bed next to me, she put the candles out on the nightstand.

It would be only a few days later that I would have sex with Dale. She dressed up in some outfit that older guys would love. Stockings, heels, garterbelt, heels. Her makeup was so good I actually complimented her on her looks.

I would take Dale on her fours, the sensation of having sex in the most taboo manner from what I heard. It was more than I imagined. I held Dale by her hips and my young body fucked without restraint. Dale didn't try to hold me back, I came too soon. I stayed inside of Dale breathing rapidly, I wanted to fuck longer and enjoy the pleasure. Dale would tell me after that I had to learn to satisfy my girlfriend too.

I turned sixteen and Dale took me to get my drivers license, letting me use his car for the drivers test. We became weekend boyfriend and girlfriend. Dale would always be dressed the entire time I was with him. He showed me his closet of female clothing, high heels and several pairs of fashion boots to wear for me during those times.

We enjoyed a year together and then one day Dale told me he had to go away, he couldn't tell me where he was going. He was dressed up as always, we embraced and both cried for what seemed like hours. I told Dale I wanted him to fuck me, I had thought about it for several months. Dale told me I should be dressed up similar to him. He put the makeup on me, found some female clothing, bought me a pair of boots to wear in my size.

Dale bought douche for me to use, to clean myself for him, like he did for me. We lay in the bed spoon fashion and he entered me from behind. Oh god it hurt, I never thought about such things until it happened. I started to cry and he added more lube to his engorged cock. He pushed his cock into my ass again, holding me tightly. It felt like he was ripping me apart and all the while he kept telling me he loved me.

At some point I think I sort of blacked out from the pain. Dale had her cock deep inside of me. She pulled me onto my fours and began to fuck my ass slowly. I was moaning loudly from pain and pleasure. Dale fucked me with a steady rhythm, his hard cock filling me and then pulling almost out.

Dale's voice soft, telling me how much she loved to fuck me. On my fours I looked under my belly and saw my hard cock dripping cum as I was being fucked. I erotic sensation raced through my entire body seeing this happen. I told her to fuck me harder, she did willingly and more cum dripped out of my cock.

Then the moment came that couldn't be held back. I felt her hands on my hips tightly, her hips slammed into me from behind. The pain ripped through me again, I cried out from more pain than pleasure. Dale couldn't hold back, couldn't be gentle any longer. She fucked me like a whore, slamming her cock into my ass and calling me a slut.

Then a high pitched sound and then I felt the hot seed of sex being pumped into my ass. Cum poured out of my cock as Dale fucked me to the last drop. She pounded me until I collapsed onto the bed, she fell on top of me with her pulsating cock deep in my ass. We lay there like that for a long time, sometimes she would thrust her hips downwards with her cock still inside but now not as hard.

I would fuck Dale later on during the night, taking her the way she had taken me. I came too quickly, the excitement of this moment was too much to hold back. I filled her hole just the way she had filled my own. We had sex until the sun started to come up......

That was our last time together. Dale sent me a letter at my Foster home telling me he was out of the country and he would contact me sometime. I never heard another word from Dale. I had turned 18yo and a few weeks later I got a letter from a lawyer saying I needed to call his office.

I called and was informed that Dale had left me a key to a storage unit a few miles from where I was living. I had a car and a job and I drove to the storage unit after work one day. I found the storage unit and opened the door. There were six medium size boxes sitting in the middle of the unit. I opened the boxes and they were all of Dale's clothes, heels, and boots.

There was a note in one of the boxes saying the storage unit would be paid for another year and after that it was up to me what to do with the items. I was lost for a while, tried to date women, having sex with them. It did nothing for me sexually, Dale had mind fucked me good. Fourteen years later I have a good job and a nice home. Most of my dates or relationships are with passable Cd's or Tranny's. I have Dale's clothes with all of his high heels and boots in a spare bedroom closet, hoping one day he will come back to me.......