My name is Willow. I used to be called Will but now I am a femboy sissy, willow is much more appropriate. This is the story of how my step Uncle made me into an ultra submissive sissy slut. I call myself a femboy but honestly sissy is a more accurate description. Right now I'm 23 but my step Uncle Reg first started having sex with me when I was 14. Here's how I lost my virginity and how that experience made me into such a slut.
By way of background, it's important to know that I was adopted at birth. My biological mother was an opioid addict. Apparently she was on such large doses that I needed to be weaned off them in the NICU. One of the effects of being born to a mother with an opioid addiction is it effects your growth so I was absolutely tiny and I still am. In addition to that, opioids can shrink the size of your genitals. So when I was born the doctors needed a specialist to check that I was actually male. My cock has never really gotten bigger than the size of a baby carrot and my testicles are about the size of chickpeas. I was adopted by my mom who was also quite young. She was a trophy wife of a diplomat. He left for an even younger woman when I was 12. Apparently the pre-nup meant she got hardly anything. So she was poor and had me to look after. Luckily she was still very hot and she managed to bag an older stud called Bruce who is now my step dad. Him and his brother Reg own a huge construction company which they started when they we in their 20s. Reg, his older brother, first saw me at a pool party and he couldn't take his eyes off me. But then again, I couldn't take my eyes off him.
He was mid forties and looked like he had spent his life in the sun working a physically demanding job. Which was true. He was 6'8 and muscular. He was in proportion too. In every way by the look of the bulge in his tight fitting swim shorts. I had just turned 13 at the pool party and my mom and Bruce were always talking about the wedding. I was an awkward geeky kid. Pale and even skinnier and thinner than I am now and I was also going through puberty leaving me even more awkward and unsure of myself. I am 5'3 and I weigh 100lbs even now. But then I was smaller and weaker which is saying something. Seeing Reg was like looking at a true Alpha male. When he came over to talk to me I must have blushed because he made a lot of effort to put me at ease.
The wedding wasn't far off and my mom was going to spend a whole summer on honeymoon with Bruce. Which meant I was a problem. Reg had an idea though and looking back, my mom should have known what he was up to. She was head over heels for Bruce so she didn't really care. She was just keen to get rid of me. Reg had suggested I spend the summer with him in his cottage on Lake Huron. He had built the cottage himself of course and it was on a decent sized island with no one else around for miles. I could spend the summer with him and he would feed me and take care of me. I could help with chores and he might even give me an allowance "if I was good!". I honestly was so naive that I had no idea that Reg was hoping to fuck my holes into oblivion. I just thought that my new Uncle wanted to spend some quality time with his nephew. I had just turned 14 when my mom and Bruce had their wedding and soon the summer was here.
So I packed my bags. Reg suggested I bring swim trunks (he preferred speedos), maybe a few sweaters in the evening. It could get cold. He also asked me for my size as he could also buy some clothes for me. I thought that was so kind of him. I was so excited when the day came and honestly I couldn't wait to spend the summer with Reg. He was so awesome. The boat ride was memorable for being so long. I imagine it was maybe a two hour ride but I had to sleep in the small berth as it was so long and warm. When we arrived it was almost evening and Reg helped with my bags. I was struggling to get up the rocks in my flip flops so Reg offered to carry me up to the cabin after running ahead with my bags. He was so strong I thought. I felt like a little kid being carried by him and when we arrived I was amazed!
It was a gorgeous log cabin like the ones in magazines. He gave me a tour and I was stunned by the size of the bathroom. it was finished with marble (how did they get all that marble there?) and there was also a bidet with a curious attachment. It looked like there was an erect cock like wand that was attached to the bidet with a metal hose. Interesting. Also the bathroom was accessible from the bedroom. Wait? just one bedroom. Apparently so. Reg explained that we would be sharing the King sized bed for the summer. I didn't mind did I? Well.. I guess I didn't.
I hadn't really even started looking at porn by this stage let alone masturbating like my other teenage friends. I spent most of my time online and I had gone down a bit of a sissy rabbit hole. I loved to look at femboys getting dressed in skimpy outfits but I had never really thought how that related to real men. That real alphas like Reg would want to fuck the sissies. So the idea of what was happening had not really dawned on me.
Reg suggested I get freshened up and he would meet me in the bedroom so he could tell me what the summer would look like. And He thought we might want to hit the sack early. I thought that sounded great. Just before I went into the bathroom he wanted to show me the bidet and how to use it. He explained that the cock shaped wand was custom made and it was used for cleaning out the rectum. I hadn't known much about fancy bathrooms and I assumed this was a standard feature. He explained that the tip goes into the anus and I could adjust the temperature and power with the taps. He really wanted me to use it before bed. I said sure and got on with it.
I had a long shower and made sure all the grime from the walk to the cabin was off. Then I used the wand in my ass which I had to admit felt amazing. It was like I was being cleaned inside and out! My little cock got erect and started to leak some precum. At this stage I hadn't ever had an orgasm so it felt strange but pleasant.
When I was done I wrapped myself in a towel and headed for the bedroom. That's where i had left my backpack which had my pyjamas in it. To my surprise Reg was standing in the bedroom totally naked! The lights were dim and I could see the shadows his muscles made on his body. He had an eight pack despite being so big. I could see the thick veins on his forearms and legs. But of course in between his legs was a real mans cock. I couldn't believe we were the same gender. His cock was eleven inches long and had a gentle curve upwards. It was incredibly thick too. Its head was wide and the shaft was a little narrower but it expanded towards the base . Reg beckoned me over. Suddenly I felt nervous.
I was alone with this massive man on this island. I hadn't expected anything bad to happen as Reg was so kind. But he was also hot and deep down the attraction was mutual. "Come here willow don't be shy", Reg said. My heart was pounding out of my chest. First of all because I knew I had to do what he asked whether I wanted to or not. Secondly because I did want to.
My towel dropped to the floor as I walked slowly towards him. He grew bigger as I got closer and that cock of his seemed to throb with his heart beat. I looked up at his manly and handsome face. My cock which was hard from the douching was now completely flaccid and limp. I was like a doll next to this hulk of a man. "Listen Will" he said. "I know you are gay and are attracted to me. That's totally okay because I am very attracted to you. Ever since I first saw you I knew I wanted to be your first. You know what I mean by that right?". "It means I want to be the first man to have sex with you. Are you ok with that?". I had the feeling that if I said no, then he still would be the first to have sex with me. I nodded meekly. I was lost for words. I couldn't believe I was about to lose my virginity to this man.
Other boys in my class talked about who they would "do" and various attempts at getting blowjobs and all that. I knew that I was a bottom and so sex for me was about being fucked and giving blowjobs. But as a skinny geeky mommys boy I had no idea how to get that. Well I guess I didn't need to try. Reg walked a few steps towards me and now his cock was just inches from my face. "Willow. That name suits you better. Willow. I want you to hold my cock. Worship it." My small hands reached up and felt its heft and it's warmth. I really could feel it throb and gently enlarge and deflate with the beat of his heart which was now also getting quicker. I held it in my hands and gently pumped its length. I couldn't get one hand all the way round it's massive girth. I was entranced but also my mouth had dried because of my nerves. Instinctively I wrapped my small dry lips around the head which had huge drops of precum oozing from his pee hole. The moistness of the precum wet my lips somewhat and I was able to suck it more. I could barely manage to get the bulbous head into my mouth. Finally my lips were on his shaft and I nodded my head back and forth. I looked up and saw Reg grinning at me. "good boy!" "Keep sucking. Your mouth is just a hole for preparing real mens cock for what they are made for. Anal sex". While I was sucking his cock I suddenly thought what he meant. This monster cock..in ...my ass? I had never even fingered my ass let alone had an eleven inch cock up it. I somehow doubted that it was going to fit. Suddenly I got scared and stopped sucking. I pulled my mouth away and looked up at Reg saying "Uncle Reg. I haven't even fingered my ass before. The only thing that has ever been up my bum was the douche. I Don't think I can do this!"
Reg smiled again. "Sweetie you can do this. Honestly I have a tub of vaseline and I am going to go slow. Real slow.' Once I cum in you it will get easier. Trust me". I realised then that this was the plan all along. Get me isolated and fuck me. All summer. I knew I had to play along and perhaps it would feel as good as everyone said. Just...his cock was massive.
I didn't know it at the time but many years after, Reg told me that he was planning to finger my ass before fucking me. But when I let slip that nothing had ever been in my hole, that was when he decided he would go in cock first. I should have kept quiet but then Reg also told me that someone as small and as sexy as me don't come along often So the first time would be as much of an experience for him as it was for me. Still from my point of view it was intense to say the least.
When I had stopped sucking he picked up the vaseline from the shelf behind me and told me to take a scoop and smear it on my anus hole. I did as I was told and was very liberal with it. He also took a scoop (a bigger one of course) and lathered it onto his meat slab. I was approaching a panic now but I tried hard not to show it. After all this was going to be my first but it sure as heck wasn't going to be my last. "I always fuck a boy the first time in missionary. That was I can watch your face as I push it in" He wasn't sadistic has he said this but it was more like a fact of life. That losing ones anal virginity was about submitting to a superior and dominant being. Reg finished lubing up his monster and stared at me frantically rubbing my anus with my skinny little hand. He was ready even though I wasn't. He picked me up and gently put me on the bed. I remember thinking he was even bigger than I had imagined. Reg easily lifted me by an ankle and placed a pillow under the small of my back so that my ass was pointed up at an angle. He had clearly done this before. I was hoping that I had used enough vaseline. The tub was big but I saw that it was half gone. Clearly he had needed a lot to layer his entire cock in the greasy lube. I was so nervous and he knew it. In fact I thought he wanted that. He held each of my legs in each hand and I remember feeling his powerful callused hands on the backs of my knees. He leaned in and pushed my knees all the way back. His face was inches away from mine. Without warning he kissed me deeply. I closed my eyes and felt pure pleasure! It was amazing being dominated by him like this! It was ecstasy! But then...Pressure on my anus. Woah that can't be his cock! It felt like an apple. No way was he going to..Plop! My anus gave way to the pressure and I broke off the kiss to open my mouth in a gasp. Reg looked me in the eye. This was it. The moment he was waiting for. It felt like my insides were on fire as he pushed further. My anus was stretching more and more and I felt the warmth of his cock deep in my rectum. He had barely begun. However he wasn't stopping. After 5 inches or so I felt more pressure. I didn't realise there was another sphincter in the rectum and mine were quite close together. He plowed through it and I felt another burning sensation. But now his cock felt actually hot inside me. I gasped again and this time Reg leaned back as he pinned my knees back further. I was folded in half and he kept pushing. Further and further. Until..I felt his pubic bone hit my bum. He was balls deep. I had just gone to the bathroom but there was an irresistible urge to pee. I dribbled a tiny amount of pee which was mixed with the precum.
Reg's domination was complete. Although it wasn't quite. He then slowly began to pull out again. It felt like my insides were being sucked out as he pulled back. I felt my inner sphincter get released then just before he had his head out of my hole completely, he reversed direction again. The burning was less but suddenly I felt a warmth building all over me. This was the second stroke but already I had felt a combination of pain and pleasure. And fullness and submission. My tiny cock hardend and Reg saw in amazement that I was about to cum! I spurted out a tiny drop of very faintly white cum after which my cock deflated to a shrivelled up worm. I felt washed out but Reg's cock kept coming. I wanted him to finish quickly but he was taking his time now. He thrust slowly in and out all the way each time. Over the next twenty minutes or so he quicked his pace. I got hard again and came but he was still taking it steady at around a thrust per second. The burning in my rectum lessened and I got hard again but I didn't cum until his pace quickened again. This time I felt him working hard. He was thrusting at two full lengths a second now and his body made a slapping sound as he collided with my butt. Phap Phap Phap was the sound of the sex and my micro dick spurted again but this time I felt a gush of scalding hot liquid in my bottom. I knew I had made Reg cum. Suddenly I realised that I was going to have a great summer.
to be continued