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All characters are over 18 years old and are consenting. Do not read if this is not your thing, anyone under the age of 18 should leave immediately. It contains crossdressing, pegging and incest.
An updated version of part 1 has been posted with the grammar checked and fixed on it. Thank you to johnnyforeigner for editing and proofreading this story.
*****
A couple of hours later I woke up on my sisters’ beds. My asshole was sore, but I wasn’t surprised; I had been absolutely annihilated by Carrie’s strap-on she really knew how to fuck. Waking them up, I suggested we put their room back to normal and maybe open a window to get rid of the smell of sex, so mom wouldn’t find out.
I picked up my clothes and returned to my room, replaying everything that had gone on earlier that day. I still couldn’t really believe it. Just by thinking about it, I was getting hard at the memories of it, although I don’t think there was any cum left in my balls. I crashed out dreaming of fucking my two beautiful sisters again and them fucking me.
I woke up at about 9 am and for some reason the first thought in my head was what Carrie had said to me just before I passed out, saying that next time they would turn me into a sissy. All I could think of that it was some funny dream, would they actually want to do that to me?
I made my way downstairs for breakfast. Mom was sitting on the barstool looking wasted. She must have had a good night with her girlfriends. Despite looking awful though she had managed to put out the usual fruit and cereal selection.
I sat down and had some granola, adding some strawberries, blackberries, and yogurt to it. Mom looked up and gave me a smile, her way of saying it is ok to talk to me.
“How was your night Mom?” I asked.
“It was ok darling. I think I had too much to drink though.” She said
“Yeah you look pretty rough, but I’m sure all the guys won’t mind,” I said not wishing to completely insult her.
“Thanks, Austin, I’ll take that as a compliment.”
“Did you meet any hot guys?”
“Really Austin! You don’t want to hear about my love life!” She said going bright red, so she had definitely got some action, but I didn’t press anymore. Mom had had a few boyfriends since dad died, but nothing that serious. She had always put us first but I think it was time she had some fun.
“Well if you did, good on you, Mom. I think it’s time you had a little fun.” She just smiled at me, I loved it when she smiled as it showed her dimples. She then went upstairs, presumably for a lie-down. Her ass swaying as she walked, she was still very attractive for her age, looking like an older version of Carrie and April.
She was about the same height as April and I, her breasts were slightly smaller than April’s but not by much and still looked very firm. Sometimes I couldn’t believe she was only 43, she looked like she was in her early 30s. Lots of people commented on how she looked more like our older sister than our mom. Whoever the guy was he was very lucky, if I were older and not her son, I would definitely want to get a piece of her.
I then snapped out of my daydream; I had become slightly hard. Knowing this was wrong but perfectly natural, but you often look for a partner similar to your parents or siblings, plus mom knew she had this effect on all guys and even some women.
I went upstairs to get showered and then dressed for work. When I went into my room there was a note from April and Carrie:
‘Thanks for last night Austin we really enjoyed it. Maybe we can do something more fun next time. Love Carrie and April. X’
It really hadn’t been a dream. What were they planning? The thought of turning me into a sissy put a slightly dreadful but thrilling thought in my head as I went to work. I couldn’t stop thinking about last night as I walked to work and I was hard all the way. Understandably I got some very wide-eyed looks. Before I stepped into the restaurant, I stopped to compose myself, I didn’t want to be fired for being a pervert.
When I went in I was told I would be training a new waitress today who, like me, was doing this as a summer job before she started college. She looked like a typical bimbo, the type of girl that would suck anyone off to get her further in life. However, looks were deceiving as she said she was going to be studying marine biology, also telling me her name is Nicole.
She had the biggest breasts I had ever seen on a girl, about a 36E; I could not believe they were natural. They were much bigger than Carrie’s and April’s and were straining against the fabric of her uniform. Our boss was a dirty bastard and made sure that all the girls wore shirts that were a size too small for them and the skirts were just long enough to cover what they had underneath.
The restaurant, although classy and posh, also had a particular reputation with its workers. It was known that some of the more well-off clients would expect a certain additional service, although I had never experienced anything too extreme while Betturkey I had worked here. We were told they expected a posh Hooters experience hence the tight and slightly slutty uniforms for the girls. Even the boys didn’t escape it, having tight shirts to show off muscles and tight-fitting pants to show off our bulges.
Nicole had the most beautiful long auburn hair with a slight wave, reaching down to her breasts. I had always been a sucker for redheads. Like most of the girls in California, she had a lightly tanned athletic body with a great set of shapely legs on her. She was ever so slightly taller than me, but then most people are.
She shadowed me for the day as I showed her the ropes, I couldn’t help noticing that a lot of the men were checking her out and even some of the women. If I’m honest, I found it very hard not to stare at her, she was one of the most attractive girls I had seen. She didn’t seem to mind all the customers checking her out though.
After the busy lunch rush, we both took a break and one of the perks of working here was you got to eat whatever was left from the previous day, which was usually a lot and it tasted great. Sitting with Nicole to eat I noticed that she had amazing emerald green eyes. I was developing a small crush on her. We then got around to talking.
“Doesn’t it bother you all of those men staring at you?”
“No, not really, I’m used to it. All the male teachers would stare at me at school. They took one look at me and assumed I was a bimbo or a slut.” I had come to the same assumption and I think she knew that I had too.
“I hope I didn’t stare too much; it is hard working here seeing as everyone is in such tight uniforms.”
“Ahhhh, you’re so sweet, you didn’t stare too much, plus I got to stare at what you’re packing!” she said with a cheeky smile, her cute little dimples showing just like mom’s had this morning.
“Well, I guess its swings and roundabouts working here then.” We then started to talk about some TV shows before it was time to go back to work.
I hated the after-lunch period, it was a slow period and all the assholes seemed to come out and eat at this time. As we weren’t that busy you’d always have to listen as to why they were so great.
Nicole looked visibly bored, “How about we play a little game, where we dare each other to pass some of the time?” She said smiling innocently.
“Ok, what did you have in mind?”
“Well, you could suggest for me to flirt with any of the customers.”
I looked around the room, trying to find the ugliest guy in the room, I had found him – a balding man in his seventies. “Ok, go flirt and tease with that guy.”
She did exactly that, bending over to collect the plates giving him a good look at her cleavage. Nicole even ‘accidentally’ dropped some cutlery, bending over from the hips and giving him and me a good look at her panties. The old man soon left and had left Nicole a massive tip. She burst out laughing.
“That was really fun, now your turn.” She looked around the room; her face then lit up. “Right see that gay couple over, every time you go over to them I want your cock to be rock hard. I’ll give you a little helping hand.” She smiled, discreetly lifted her skirt up and pushed her pink panties to the side giving me a good look at her pussy. It folded inwards with a landing strip of pubic hair. It didn’t take long before I was hard.
Nicole’s eyes widened at the now-massive bulge in my pants, giving a little smile in appreciation at my manhood. I then walked over to the gay couple their eyes staring at what I was packing in my pants. I took their orders and walked away. Nicole was nearly in hysterics but kept it together.
Still hard I brought them their food, plus anything else they needed and went back to doing my other duties, mainly collecting plates and cleaning tables. Nicole was trying to help but would burst out laughing every now and then. It was definitely a way of flirting I had never encountered before.
Eventually the gay couple had finished and called me over to pay for their meals, I told them I needed to bring the card machine and bill over to them. Most people paid by card in this restaurant, but always had cash for tips.
When I got to the cash register for the card machine Nicole took a hard look at my crotch. “I think you’ve gone soft again, let me help with that.” Nicole slid her hands into my pants, wrapping her dainty hand around my cock. It felt like her hand was made specifically for my penis. I looked deep into her emerald green eyes; I could see the lust she had for me, both of us lost in the moment.
My cock started throbbing in her hand and we both snapped back into reality. “Right I think that should do. Go on then give them their cheque.”
I walked over to their table, my massive hard-on bulging against my pants and handed them the bill. Once again, they were staring at my straining cock while I set up the card machine. I swear all these women teasing me are going to be the death Betturkey Giriş of me. Having paid the bill, they gave me a large $100 tip.
“Next time, if you need any with that help just ask. We’ll be more than happy to help.” One of the gay men said to me, his boyfriend nodding in agreement.
Once they had left both Nicole and I burst out laughing, it was pretty funny. Her dare seemed to be a lot funnier than what I had done to her. Not long after our shifts finished, I decided to give her most of the share of the tips, she had definitely deserved.
“I can’t take 80% of the tips, it’s not fair, after all, you pleased those men more than I did mine. The tight bastard only gave me a $40 tip!”
“Ok then I’ll take 30%, but you have to promise me to go out for some drinks one day?”
“That seems fair.” She then gave me a little peck on the cheek. She then left swaying her beautiful round ass. God, she was so hot. Not long after I left and took what felt like a really long walk home.
When I got back home, I planned on having a shower, get changed and then chill out for the rest of the day. When I got to my room, however, I noticed a post-it note on top of my laptop. It read:
‘Open me. Enjoy. Love Carrie and April. X’
I sat down and opened the laptop, a private window opened and I was greeted with a Reddit forum. I would often look at Reddit for the NSFW content, my particular favorites being Gone Wild, NSFW, and Real Girls. This particular Reddit forum was called Sissies and as the name suggests it was guys dressed up as girls.
This was obviously some part of their plan, maybe to see if I would agree to dress up the next time we played. My interest peeked, I would definitely consider doing it as I scrolled through the images. A lot of them you could never have guessed they were guys; they were that good until you saw that they had cocks or no breasts. To my surprise, I was getting hard, enjoying it, imagining what I would look like dressed up and completely shaved.
I closed the lid and went to the bathroom. It felt a little odd getting turned on by it, but that however made it more exciting. Walking to the bathroom April saw me and looked straight at my pants. She had noticed the bulge and just gave me a smile; I knew she would put two and two together and tell Carrie she had seen me. I got into the shower and turned the taps to cold as they would go, luckily it worked and my boner went away. Apart from that the rest of the evening was uneventful, I had dinner, watched some TV and then went to bed as I had another gruelling shift at work ahead of me.
When I woke the next morning, I knew I didn’t need to be at work as early as the day before, so I went on a run for about thirty minutes. Running usually cleared my head, but all it did was make me want to explore this idea of becoming a bit of a sissy.
Having finished my run, I was more confused than I had been when I had woken this morning. I had a quick shower, some avocado on toast for breakfast and then started to walk to work. About five minutes into my walk my phone beeped, it was a message from Carrie.
‘We know that you enjoyed what we found for you on Reddit. When you’re on your break at work, we want you to watch this. Enjoy. X. Ps definitely NSFW.’
Great. My mind was now flooding with what they had found and what would happen if someone caught me watching.
When I arrived at work Nicole gave me a smile, and god was it beautiful. My asshole of a boss also came over and said that Nicole wouldn’t be shadowing me as closely today, but if she needed any help, I was expected to help her out. It was disappointing that I wouldn’t get to spend as much time with her today.
The shift went a lot slower today; Nicole, however, would do things to catch my eye. Mainly showing her panties slightly when she was bending over, or brief glimpses of her tits, she wasn’t wearing a bra today and she didn’t need any help. The restaurant was filled with the usual tight, rich cunts you wouldn’t even piss on to put them out if they were on fire. A couple of them slapped some of the waitress’s asses and a few women pinched my ass.
Eventually it was time for my lunch break; I went to the break room on my own and leant against the wall so I could see anyone coming in. Following the instructions sent by Carrie I clicked on the link on my phone, almost out of some duty to her, but mostly out of curiosity. The link sent me to Pornhub, the video was titled No Longer A Man! Sissy Loves Cock Now!
The video started, a woman was narrating while different clips of shemales were being fucked or sucking off dick, some of them dressed in lingerie. The voice saying that you want to take alpha cock, that you were born to be sissy. Once again, I was getting turned on by the thought of being a sissy and serving my sisters’ dildos.
The video was telling me I would need to dress slutty, wear makeup and become a bimbo slut. Wanting to feel their big cocks in my tight fuck hole, pressing Betturkey Güncel Giriş against my body. At this point, I’d have done anything to feel my sisters’ dildos in my ass and spreading my legs to please them. The video eventually ended with a compilation of cum shots, just as hot as regular porn.
As the video, ended Nicole walked in. I quickly closed my phone.
“Something’s got you flustered. What were you looking at?” She asked.
“Erm… Oh, just some porn my stupid friends sent me.” I replied trying to be as smooth as possible.
“Well, whatever they sent you has sure got you hard. If only there was someone to help with your problem. Oh, look there is.” She said looking rather innocent.
She walked towards me and put her hands on my rock-hard cock, rubbing me through the fabric of my pants. Sliding her hand into my pants, she started to slowly jerk me off.
“Just to be clear, I don’t normally do this on the first date. A hand job is normally reserved for a fifth date and we haven’t had our first yet. Don’t look too worried, just cum in my hands when you’re ready, and I’ll deal with the mess.” She said in a rather business manner.
She started to stroke me harder and once again I looked into her eyes and all I could see was lust. I could tell that she wanted to just jump straight onto my cock, but she was using all the self-control she had not to. Thoughts of fucking her came into my head, as well as thoughts of me lying there and both of us getting fucked by dildos and hard cocks. She really wanted to have my cum, speeding up her motions, her hand gilding and dancing across my shaft.
She leaned into me and whispered huskily, “That’s it cum for me, I want to taste your cum.”
“Ah shit Nicole, keep doing that. Fuck you’re so good. Fuck, fuck, fuck! I’m cummmmmming.” I came into her hands. When my dick had finally stopped twitching, she let go and started to lick the cum off of her hands. She looked very sexy with a tiny bit dribbling from her fingers onto her chin. Making sure she had every last drop she said,”Mm, that was very tasty. I hope I helped. Oh, and here is my number for that drink one day.”
I straightened myself up and left the staffroom, she settled down and ate her lunch. The rest of the shift went on as normal. I got to leave a little earlier, which was a nice change. Just as I was leaving, I got a text from Carrie:
‘I hope you enjoyed the Sissy Hypno video and that it got you hot for what we are going to do to you. I hope you didn’t get caught. X’
I replied quickly:
‘I was surprised how much it turned me on, I almost got caught, but was given a little assistance with my boner.’
‘Lucky you. X.’ was her reply.
When I got home, I knew I could relax and have the next three days off. It was great having a three-day weekend. I also knew that Nicole had the weekend off, so thought it would be a good time to meet up at a coffee shop. I texted Nicole hoping not to be too desperate.
‘Hey, you free this Saturday for a coffee?’
‘Sure. How about we meet up at Gio’s Coffee Shop at 1 pm. ?? X.’
‘K. See you then.’
The rest of the late afternoon I watched a mindless action series, I always found them a great way to get some entertainment without needing to follow every aspect of the show. It was about an LA cop who had turned rogue and seeking revenge against the police department.
At about 6:30 Mom called us to dinner, she had made simple chili due to having such a busy day, it was still really tasty though. It looked like Mom could definitely do with a night off and let some steam off. She didn’t get the chance to do this much.
“Mom why don’t you go out tomorrow night. Have some fun. I’m sure me, Carrie and April can look after ourselves.” I suggested.
“Funny you should say that Austin, I was going to go out tomorrow but I changed my mind. I worry about you guys when I’m not here.” she said. Sometimes it seemed like she was a prisoner in her own home, almost like she had developed a sense of Stockholm Syndrome to us.
“Mom, Austin’s right, let your hair down. It’s not like we are going to starve.” April added.
“Alright, I’ll go out then.” She said somewhat relieved.
“I’ll buy a pizza and we can have a film night or something, and mom you don’t need to get back early, stay out all night and have some good fun.” I said.
“I’ll try and have fun. Maybe I’ll stop out extra late so you all worry about me.” She said sarcastically.
Once we had finished dinner, I cleared the table and loaded the dishwasher. Mom and the girls settled to watch some mindless dating reality show – the type of show where all the men are buff as fuck and the women are all teeth, tits, and toes. I couldn’t stand it, just hearing it in the background I could feel my brain turn to mush and my IQ drop.
I went to my room and played some Pokémon and Counter-Strike. When I next looked up at my watch it was already 11:30. Deciding it was time for bed, I got ready and tried to fall asleep. My mind, however, couldn’t switch off. I decided to scroll through Real Girls on Reddit, eventually getting bored I looked at Sissies again. This could be me tomorrow. That thought really excited me and allowed me to switch off. The sooner I got to sleep, the sooner tomorrow would come and my fate with destiny.
Ben Esra telefonda seni bosaltmami ister misin?
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