Guys, Girls, and Sissies Pt. 01

This story contains sexual themes that aren't everyone's taste. If the title and tags of this story don't appeal to you then don't read ahead. For those who enjoy these stories, it starts off slower but ramps up and is worth the wait. Enjoy.

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Looking out of the car window I watched the woods, slowly become the suburbs, which in turn finally gave way to the concrete labyrinth of the inner city. The past three-day weekend had been the craziest of my life, and I knew that I, (and my ass), would never be the same again, but I was happy with that. Let me take you back to Friday morning.

Having recently split with my girlfriend of 3 years I had been moping around at work when Daniel invited me out for a weekend in the woods with some friends. I didn't know him too well and seriously contemplated saying no to this offer, I just wanted to be alone and feel sorry for myself. Daniel was a well built, confident guy who had never had a problem getting girls, whereas I had only had one relationship and it had ended when I caught her cheating on me with a 19 year old jock. But I couldn't sit around feeling sorry for myself forever and besides, Daniel said that Jess and Amber would be coming along too. Both were mid twenties like us and had faces and bodies that made all of the men swoon. Maybe I'd be able to get with one of them?

During the ride down, Daniel and Amber sat in the front while I sat in the back with Jess. They seemed to know each other really well and during the few hour car ride had no end of old stories and inside jokes to tell each other. I didn't really know any of them very well but tried to join in and they even laughed at some of my jokes which made me feel better.

At one point when I was dozing my way through the car journey, I saw Amber reach over to Daniel and lay her hand on his jeans. This got my attention but I tried to look asleep as she looked back at me quickly to make sure I wasn't awake, she began to stroke his crotch through his jeans. She had a smirk on her face as Daniel turned to her.

"Wow, still got a big monster in there," she giggled quietly.

"I plan to use it soon," he grinned back.

"Who's the lucky gal?" she asked inquisitively.

"You already know..." he said back with a knowing glance.

I didn't even know that him and Amber were going out, let alone going to have sex on our weekend away? At first I felt a bit deflated, but soon realised that mean't Jess would be all alone, maybe I could bag her for myself! I wondered what Jess thought of their public display but without showing that I was awake I couldn't see her expression. I closed my eyes again with a smile on my face.

*******

"Hey!" a voice suddenly shouted, as I simultaneously felt a great weight hit the top of my thighs. Jolting up I looked to see Jess sitting sideways across my lap, looking up at me.

"Come on sleeping beauty, Dan has already taken our stuff inside!" she laughed.

This had all taken me completely by surprise, this hot brunette was sitting on my lap, her ample breasts just below my nose, my peripheral vision just glancing the top of her perfectly formed orbs. Her lips looked lush; full and red. All of a sudden I felt her reach down to my thigh and for a second, she was making a sexual advance on me already...

"What's this?" she said starting to laugh heavily, I felt her fingers rub my small cock through my clothes, "I thought I was sitting on your headphones, didn't realise you were getting hard just because a girl sat on your lap!" She opened the door and stepped out, leaving me sitting up straight with a very small tent in my jeans.

"Don't worry," she continued, "Not all guys can be endowed like Dan, besides little penises are what make his look so impressive!"

Totally embarrassed I quickly stepped out of the car and followed her, my head full of thoughts, 'you idiot, she's never going to get with you now. How could you get hard at that? Why did you give her the chance to feel how small you are, she will never fuck you now and she'll probably tell everyone!'

My girlfriend was the one who had first told me I was small down there, 3 inches hard had felt impressive to me until she informed me that the average was 6 inches and her last boyfriend had been 8 inches. We didn't have sex much after that, in fact I hadn't had sex with anything but my hand for 4 months and I was painfully horny at even the slightest feeling as this showed.

I followed her shapely ass along a small track until we arrived at a log cabin, the woods around were a beautiful sight and the cabin extenuated it. Stepping inside the large building, Daniel and Amber were just finishing unpacking their bags and had already changed into swimming shorts and a bikini.

"Oh I forgot my bag, I'll just go and get it," I said looking for an excuse to get away for a moment to gather my thoughts.

"Don't worry about it!" Daniel boomed, "I dealt with it when I grabbed ours, besides were all going to go down to the stream now, you coming?"

Jess sensed my hesitation and grabbed my hand before I could answer, "Come on, we come here all the time and the stream is great, I promise you'll enjoy it," she said enthusiastically while staring into my eyes.

Just looking at her made me agree to anything she said and within 10 minutes we had made our way through the forest and to the stream. Upon our arrival, Jess stripped off her shorts and top to reveal a swimming costume already underneath and followed Daniel and Amber into the warm, gentle stream of water flowing past. I hadn't had time to change so I still had my usual clothes on and with no idea how to get back to the cabin I was stuck with them on.

"What are you doing? Get in," Jess called as she stood with her ankles in the stream.

"I don't have my swimming things with me, " I called back dejectedly.

"Just take your clothes off and come in in your boxers," she laughed while wading out until the water came up to her ass, "Were not wearing much anyway!"

"Thanks, but I'm okay, you guys enjoy it," I said as I sat down on the edge. She looked disappointed for a minute but quickly joined in with the other two, splashing each other and admiring Daniel's chiselled frame and thick biceps.

For the next few minutes I sat on the shore, but I couldn't take sitting here with those beautiful half naked girls just meters away and eventually gave in. Stripping off I left my clothes by a tree a few meters from the edge and begin entering the water in only my boxers. The girls wolf whistled and made a big fuss of me as I waded towards them and once I had adjusted to the water it wasn't so bad. We messed around in the stream for almost an hour and apart from one point where I fell head first into the water, it had been fun, the girls were very touchy with each other and us and I soon felt like part of the group.

At this point Daniel had gotten back out of the water and sat on the shore when he called back, "Hey girls, give us a show."

I had no idea what he meant but I watched in awe as the two girls giggled and walked towards the edge so that only their ankles were still in the water. Not wanting to miss out I went to step out of the water but was hit with a sudden realisation, my white boxers had become completely see-through! Submerging my groin back into the water so that no body could see me naked , I could only see the girls from behind when they performed for Daniel.

They began by making out, holding each others faces and open mouth kissing, they looked in heaven as they licked and bit on each other's mouths. Occasionally they would look back at me so I could see what was happening but most of the time they looked forwards, showing that this display was for Daniel. My last girlfriend was so vanilla, I had only seen things like this in porno's yet here it was happening right in front of me. This continued for a few minutes until they began to grope each others boobs through their swimming costumes and within 5 minutes both girls had their boobs out and were roughly stroking each other through their bikini bottoms.

I couldn't believe my eyes, why were these girls doing this for Daniel? It was like his voice had them in a trance to do whatever he says. I wasn't complaining though, I was mesmerised, my cock was rock hard but I was too self conscious to get it out with them there and my boxers see through. Daniel however wasn't self conscious at all and soon pulled out his large cock from his shorts and begin to pump it in front of them. It was only a few inches bigger than average in length but the girth was maybe 3 times mine and for a second I couldn't take my eyes off its glistening head as he gently pumped the shaft.

The girls loved this and played with each other more and more until Daniel finally shouted, "Shit girls, I'm cumming!". The two girls stopped and watched in awe while biting their lips as Daniel's cock exploded, shooting stream after stream of cum.

Turning around to me, Jess spoke while trying to catch her breath and collect up her clothes, "Hope you enjoyed that show you perv, let's go back to the cabin."

"Er, Jess, I er, my boxers have become see through, could you grab my clothes from that tree up the top," I said pointing.

They all began laughing at my misfortune as she walked up the bank to the tree. To my horror, she turned towards me after a few seconds and shouted back, "There's nothing here, you sure it was this tree?!"

"Y, yes," I said, the words caught in my throat. Oh god I will have to walk back like this, I thought to myself as I began panicking. I looked around but that was definitely the tree I had left them by, what would I do?

At this moment, my heart leapt as Amber threw me a towel out of nowhere.

"Oh, thank you, thank you," I said back as I breathed a sigh of relief. Stepping out of the stream I only showed myself for a second. My rock hard, 3 inch cock strained against my see through briefs before I could cover it. I think they all saw something because they all began smirking but wouldn't tell me what about. Me and Amber made our ways up the bank to a giggling Jess and Daniel. I overheard Daniel saying "...told you so..." but I didn't understand and they told me not to worry about it as we began walking back. After a few minutes of holding this towel around my waste I could feel my hands becoming sticky. I tried rubbing them on the towel but it didn't make it any better.

"Having trouble back there?" Jess laughed while looking over her shoulder.

"Er, no, I'm okay," I lied back.

"Wait a minute what's that," she said stopping and examining the towel, "Oh my..." she began howling with laughter.

I was confused for a second but looking closely at the towel I could now see what she had seen, several ropes of thick white cum clung to its surface. The ropes of cum were horizontally across my whole front and were complete lines except for a few patches where I must have run my hands through trying to hold it up.

"Oh man! I'm so sorry dude!" Daniel called over, his words seemed sincere but I thought I could sense some amusement in his voice, "I must have shot all over it down at the stream, I'm really sorry man."

"It's okay," I replied trying to sound cheery and calm. I felt disgusted but couldn't bring myself to take it off and walk back in the nude.

Then Amber spoke up and grabbed the towel, "Oh no, you guys are terrible, look how red he has gotten, you've embarrassed him!" She then proceeded to quickly whip it round and wrap it back around my waste with the cum stains now on the inside before I could stop her.

Not wanting to seem ungrateful I thanked her and began walking again but the laughing didn't stop all the way back to the cabin and neither did the squelch every time I took a step causing the towel to stick to my legs.

*********

Stepping inside of the cabin I was totally embarrassed, worn out and horny. All I wanted to do was get dressed, go to my room and sit on my own. Everyone quickly went to the kitchen and started making drinks as I began searching for my bag. After a few minutes of finding nothing and even going back to check the car to see if it had been left there, I walked in on them all in the living room.

Still wearing the cum stained towel I got their attention, "Hey, have you guys seen my bag? You said you had brought it out but I can't find it anywhere?"

"You sure it isn't in your room? I'm sure I put it there," Daniel replied looking only half concerned.

"No definitely not, I checked your room too and no sign of it."

"Check the girls room, maybe I put it there by mistake."

Turning to walk away, Jess jumped up and spoke as she put an arm round my shoulder, "Come on, I'll help." Suddenly the holiday didn't seem so bad with a hot girls arm around me as we went up the stairs to their room.

Opening the thick door, we were greeted by a massive bedroom. Just large enough for two double beds, two medium sized wardrobes and a few meter gap between the beds to walk in. It only took a few seconds to realise that none of the bags on the floor were mine.

Dejectedly I looked at Jess, "I'm so sorry to cause all of this trouble but I need something to wear, do you think Daniel will lend me something?"

She smiled and stroked my hair, "Aw dear, there's no way that you will fit in any of Dan's clothes, no offence but he is a giant compared to you! No, no but don't worry, I have something that might fit you."

Surprisingly, the cloths she was looking for were at the top of her bag and she pulled them out. They consisted of a pair of pink shorts that barely had a leg part at all, and a skimpy white crop top. "Here you go, I know they aren't perfect but there's only us here and you wouldn't want to walk round naked with your little guy hanging out," she said winking at me.

"Thank you, but er, they are a bit feminine, is there any chance that, er..." I stumbled before she interjected.

"No silly, these are unisex. Just get changed and we can go and have some... fun," she said with a sly smile. I wasn't convinced but whatever she meant by fun I was up for it.

As I waited for Jess to leave, she didn't; then she spoke, "Don't worry I have seen many cocks in my time, don't be embarrassed just get on with it and I'll hand you the things as you need them."

Sheepishly turning so that my back was to her I dropped my towel as she handed me a thin stringy piece of material. She must have had it hidden underneath the others because I hadn't seen it before, it was a laced, thin, pair of panties, barely wide enough to cover my cock and definitely female looking.

"They're all I have spare, but don't worry, no one else will know," she said reassuringly.

A quick glance at her told me she was losing patience and I should be grateful for anything. It was me who had lost my bag anyway wasn't it, not her? Tentatively I slid them up my sticky legs. My ass must have looked quite the sight, two pale, naturally hairless buttocks with this pink, silky lace spread between them. As for the front, my cock could sit in them uncomfortably but my small balls fell out of the sides. Not looking her in the eye I reached back and instead of the shorts she passed me the crop top. Quickly sliding it on without hesitation, the white fabric felt soft on my skin and actually fit my slender frame well. Without a female's breasts though the front didn't look quite right, it would look much better if I did. Wait what was I saying?!

Reaching back again she passed me the pink shorts and although extremely tight I finally managed to edge them up my thighs until they hugged me well. My cock and balls were pressed tightly against my groin almost painfully, and the way it gripped my ass had made the panties wedge up between my ass cheeks.

Turning to face her, I could feel myself burning red, "Oh my, you look beautiful!" She gleamed.

I wasn't sure I liked being called beautiful, I was a guy after all wasn't I? But her compliment and smile persuaded me to follow her back to the living room in almost a trance.

When we arrived back, I was shocked to see bisexual porn playing on the television. Amber and Daniel were on separate sofas and as I entered, he didn't once take his eyes off me. Feeling slightly self conscious I stepped towards the sofa with Amber on but was yanked back by Jess and pushed over to Daniel's sofa where I practically fell on top of him.

"This is the girls sofa!" she joked, "You're not a girl... are you?"

I barely heard this question as I fell face first onto Daniel. It took a moment for me to regain my footing and only as I stood up did I realise that my face had been resting on his big, hard man meat. Daniel smirked before yanking me down onto the sofa next to him after complaining I was blocking the TV. The sofa was small and spongy and very quickly I was sinking into it and being pressed against the side of it by Daniel. The porno now showed a guy and two girls taking turns sucking on a massive cock, their eyes full of lust and the main mans moans echoing around the room.

I tried to concentrate on the film but every time I looked out of the corner of my eye, the girls and Daniel seemed to be looking at each other, maybe they had seen this one before? After a few minutes I could feel Daniels hand resting on my thigh, the feeling should have repulsed me and while it didn't like it, I didn't hate having another mans hand on me. Wait, what?

I persuaded myself that I didn't want to make a fuss and so kept quiet. Maybe it was my imagination but Daniel's hand seemed to be stroking my leg more and more as the film went on. A strange feeling inside me only got stronger as the film went on and all of a sudden I inadvertently felt the urge to cum, I tried to stop it by looking away from the film but glancing back at Daniel, he seemed to know and moved his hand to touch my cock through my trousers. Like a pulled trigger, I instantly went over the edge and came hard. I could see stars as Daniel quickly pulled back his hand and grinned as I lost myself in orgasm. I was senseless for what felt like hours but was probably a few seconds before Jess yelled across the room.

"What have you done you idiot! My shorts! Did you just cum in them you twat!?"

Sheepishly I came back to reality, I don't know what had happened to me, was it the film? Was it the sexual tension from the stream? Was it Daniel? Or did I get so lost in the film that I imagined him touching me? He was straight though right? I was straight? Right?

"That's it! Come here Mister. I can't believe you have done that in my shorts that I lent you!"

Grabbing me by my top she pulled me up, making me stand in the middle of the room, the shorts squelching around my cock every time I moved. Looking over at Daniel he seemed totally unfazed but Amber was shooting me daggers from her eyes. Roughly pulling my shorts and panties down I didn't stop her, I was so humiliated that I couldn't move and almost felt like I was watching this in happen in third person, this couldn't be happening to me. I was lost in thought until I suddenly felt a tight pressing on my balls and before I could react a tight band snapped around the base of my cock. Looking down it was one of those cock rings, except this one was black and very tight, almost painfully so.

Looking up at me she took a deep breath and spoke, "Look, I'm sorry for getting so angry but you've ruined my clothes. I can't wear them again now that you've orgasmed in them. But, I guess that's okay, you needed something to wear for the whole holiday anyway and this will stop you from getting hard and having any more little accidents in them, okay?"

"Jess I'm so sorry, where did you get that... er. I don't know if this is necessary, I can be trusted," I mumbled before she stopped me with a finger to my lips.