Alexis' First Time Ch. 02

A few people seemed to enjoy the first story I wrote so I thought I'd give Ch. 02 a go. Again this is not a true story but you never know, one day it might be.

After my first time being fucked, I wanted more. So back to the site where I met 'Daddy' from the previous to chapter to see what I could make happen. I'd been on the site for a number of months and got talking to the hottest girl while I was on there. She was called Keira, I'd initially messaged her asking for advice about dressing and getting fucked, and she was amazing. She was so helpful, encouraged me to buy my first dildo and provided some amazing advice. The only problem was that she lived miles away from me but we were determined to make something happen.

We exchanged messages for weeks, trying to plan where we could meet, who we could get to meet us there and we eventually came up with a plan. We planned to meet in Manchester, figuring there's a big gay scene in the area, we could arrange to meet a few different people. Keira told me that she'd managed to get an older gentlemen who'd fucked her before to travel down to Manchester for some more fun, so I decided to ask my Daddy if he would like to join us and he was more than happy to when I told him there would be more than one bottom to fuck. A little side note... I'd found out his name was Steve!

The weekend soon came around, I packed my little bag full of Alexis' goodies and made my way to Manchester, excited for my first meeting in person with Keira. We decided to meet earlier in the day to meet each other and have a catch up before locking ourselves away for the afternoon. I travelled in my boring drab guy clothes wearing a cute little thong that said 'today is going to be a good day' underneath but I knew Keira was going to look all glam when I met here.... and I was not disappointed. She looked amazing wearing a cute little dress with tights, I could only dream of looking that good all dolled up. I was a complete bottom but if I was ever going to top someone, Keira would be that girl. She greeted me with a massive hug and I had to apologise straight away for two things, my hand slipping down and squeezing her arse and the fact that I was hard and it was probably pressing into her stomach.... talk about embarrassing. Despite having never met, it was like we'd known each other for years and hit it off straight away, deciding to go shopping before we meet up with our friends later.

I was still nowhere near confident enough to go out dressed so I stayed in my guy clothes whilst we headed into the main shopping centre. First stop, Victoria's Secret, is that cliche? I don't care, why wouldn't a guy want to shop in there. Keira had been given some money by her friend, Martin, to spend on herself before later, whereas Steve, had given me some money cause he wanted me in a different outfit. After entering Victoria's Secret we both kind of went our separate ways around the store, I was in heaven. I had never seen so many knickers. I was picking up all the different styles, g-string, thong, cheekies, brazillian, hipster and bikini. I normally shop online but this was weird, I'd almost forgot that I wasn't dressed when I was approached by a young sales assistant.

'Is there anything I can help you with?', she said. I completely froze when I turned to look at her, she was stunning. Lovely smile and an amazing figure. I could already feel my face turning red and it only got worse when I felt Keira appear behind me. 'Is this the special lady your shopping for?', the sales assistant whose name tag read Abbie asked.

Before I even had chance to respond, Keira beat me to it. 'He's actually shopping for himself today, is there any chance you could help him pick out a few new pairs of panties please? He wouldn't tell you himself.' She leaned over towards Abbie, 'He's actually wearing a pair right now.' I wanted the ground to swallow me whole, but Keira had always provided good advice so I trusted what she was doing.

'Of course, your not the first guy I'll have helped buy panties, so don't worry about it. Do you have any favourite styles?'

Abbie immediately put me at ease and I felt better. 'Erm, I normally wear either thongs or brazillians, I like them to show a bit of cheek.'

From there Abbie led me around the full store picking out numerous pairs of panties for me, she even showed me the strap of the thong she was wearing as she said they were super comfy and didn't feel like she was wearing knickers. At the end of the shop, she even took me to the till to avoid any further embarrassment but I was super relaxed now and couldn't wait to try them on when we got back. I met Keira outside where she also had a bag full of goodies and we decided our next stop would be Ann Summers where we could both pick out a matching outfit for later.

We walked into Ann Summers and it was lingerie heaven! I was like a kid in a candy store, I thought Victoria's Secret was good but this was even better, the lingerie was all extremely sexy and the choice of sex toys was amazing. We both decided to settle on a sexy schoolgirl outfit that came with the little skirt, blouse and a red tie. For underneath we decided on matching red lingerie, with black stockings. I went for a thong bottom but Keira opted for cheekies. We decided to try everything on just to make sure seen as though we needed it for this afternoon. We headed out to the fitting rooms, I'm sure I got a few quizzical looks from the sales assistants but I was miles from home and I didn't care... I'm sure they'd be tweeting about it later. Once out of sight we both went into the same changing room, Keira seemed a little shocked but I gave her a playful slap on the arse and told her to get in there.

Once we got in, I locked the door behind us. I'd never really undressed in front of anyone else whilst wearing lingerie other than when I got fucked so this was still a bit weird for me, but Keira immediately put me at ease. She quickly took off her jacket and lifted her dress over her head before shimmying out of her tights, leaving her in the cutest bra and knickers I'd ever seen. They were white lace, the knickers were cheekies, they almost made her look innocent... but I knew that wasn't the case.

All the while she was undressing, I was just mesmerised. She was beautiful and just looking at her, thinking about all the mischief we could get up to had caused a major problem in my pants. Keira turned to face me, 'Come on, you need to try the clothes on', she said reaching to unbutton my jeans and slowly pulling them down revealing my red thong which had a spot of precum.

'Oh my God, those are the cutest', she said as she rubbed the front of my thong causing me to bite my lip in pleasure.

'But we're going to have to do something about this before we leave.' Keira dropped to her knees in front of me, pulled my thong to the side and swallowed my cock whole causing me to let out a huge groan. I knew from our messages that this wasn't her first blow job, but this was mind blowing. I had to lay down to prevent my legs from giving way underneath me.

She was kneeling in between my legs slowly licking the head of my cock taking me to new highs everytime she used her tongue to tease my cock. I'd never thought about topping but I wanted a piece of this ass, I got Keira to spin around so that we were now in a 69 position. She went back to work on my cock as I pulled her knickers to the side, freeing her cock and giving me access to her asshole. I buried my face into her asshole and began using my tongue to get her nice and wet. This caused her to moan around my cock which was bringing me closer to the edge. But there was no way this was ending without me fucking her.

Being taller I was able to flip the 69 over and immediately swallowed her cock whilst I inserted a finger into her arse. I never took my eyes off her whilst doing this, watching her eyes roll into the back of her head from the pleasure really got me going.

'You want me to fuck you baby?', I asked, knowing full well what the answer was.

I pulled out the lube and condom from my bag, making sure both my dick and her ass were completely lubed. We didn't have time for a long fuck but I was going to make sure we both enjoyed this. I slowly pushed my cock into her ass, God she was tight. I gave her chance to adjust to my cock being inside her. 'Come on, just fuck me.' That was all the encouragement I needed, I really picked up the pace but due to the amazing blowjob she'd already given me, I knew this wasn't going to last long and within a couple of minutes, I had to pull out, I ripped the condom off and Keira took my cock in her mouth once more before I erupted and she swallowed everything I had to give.

Keira made the first effort to get up and get dressed, but before she could put any more clothes back on, I got onto my knees in front of her and begin to tease her cock. Getting her nice and hard before licking my way from the base of her cock straight to the tip and then taking all of her cock down my throat. Bringing her to a quick climax, I swallowed all her cum before getting myself dressed. We left the changing room, paying for what we'd bought and then headed back to the hotel. We knew we had a couple of hours to get ready before our guests arrived. On our way back to the hotel, Keira received a text message from Martin... it read: Heyy, just bumped into a couple of old friends, hope you don't mind if they join us. See you later ;) M x.

Keira quickly responded to say that was more than okay and we quickly headed back to the hotel to get sorted. Neither of us could hide the delight from our faces as we practically skipped back to the hotel knowing that in a few hours 4 guys would be using us like the cock sluts we wanted to be. Once back at the hotel, we quickly stripped out of our clothes and into the shower, shaving all the hair from our bodies and making sure we were nice and smooth for our guests. This was also the first time that I was going full en femme. Keira had been nice enough to offer do my make up and I brought a wig that I'd bought a while ago. Once we were both freshly showered, we put on our robes and we sat at the dressing table and chatted whilst Keira applied her own make up before sitting me in the chair and working her magic. She wouldn't let me look at myself though, not until I had the full outfit on as well. Once she'd finished my makeup, she placed the long blonde wig on me and we both started to get ready.

Laying both are outfits on the bed we stripped off our robes before first sliding our stockings up our legs and attaching them to our suspender belt. The feeling was incredible sliding the stockings up my freshly shaved legs. Next we slipped into the knickers that we bought before putting on our bras. Next was the schoolgirl uniform, the blouse and skirt was enough and we decided against using the ties, luckily we both wore glasses which added to the affect. Now, for the first time ever, I was able to look in the mirror and see what I looked like en femme. I turned and faced the mirror and I was lost for words. Keira had done an amazing job and I felt amazing.

'Oh my god Keira, you've made me look amazing, we so need to hit the town while we're here!!!'

We were both ready, we placed the condoms and lube on the bedside table and settled in to wait for our first guests to arrive. Although I had a feeling that some condoms wouldn't get used or maybe all of them wouldn't. We didn't have to wait long before the first knock at the door came. I skipped over to the door, and let the first guest in. It was Steve. I greeted him with a quick kiss and led him into the main part of the room, he couldn't resist a cheeky grab of my ass as I walked away from him.

He came in, took a seat and I grabbed him a drink from the mini bar making sure that when I bent over in front of him that he could see up my skirt. We all sat and chatted whilst we waited for the others to arrive, giving Keira chance to get to know Steve, and shortly after there was another knock on the door. In stepped Martin, along with his two friends who he introduced to us as Tom and Charlie. We all got to know each other over a few drinks and I think we were all waiting for someone to make the first move.

I got up and headed over to get another drink, trying to tease them as much as possible I bent over as far as I could and one of our new friends, Charlie, spanked me as I bent over causing me to let out a bit of a moan. He then grabbed me by the waist and pulled me down so I was sitting on his lap before kissing me passionately. For a minute or so I forgot how many of us were actually in the room as his hands roamed my body.

'Ooopps, looks like I ruined your makeup baby, sorry.' I got up off Charlies lap and quickly headed to the bathroom to reapply some lipstick. It took me a while as I'd never really done it before but whilst I was in there I could hear some light moans and groans coming from outside the door. I headed back out into the main room and there was Keira on her knees with Martin's cock in her mouth and wanking off Tom at the same time. Steve and Charlie were both sat slowly stroking their own cocks whilst watching on. Between the 4 of them we had 4 decent sized cocks to play with 6.5" being the smallest to Tom having at least 9" to play with. We were in for a good time.

Not wanting the other two to feel left out, I dropped to my knees in front of Steve before taking licking his shaft slowly, making him gasp with pleasure. I looked over towards Charlie and gestured for him to come over and join us. A little over a month ago, I had never touched another mans cock, now here I am, dressed as a slutty schoolgirl with one cock in my mouth and another in my hand. I kept switching between the two cocks in front of me. Keira was much more experienced than me so I was doing my best to mirror what she was doing. After working both cocks for nearly 30 minutes Charlie pulled me to my feet.

'I think it's about time we got these sluts ready to be fucked.' Charlie said before he and Steve stood one in front of me and another behind. Just being called a slut and the anticipation of the fucking I was about to receive had me more excited than I'd ever been. Tom and Martin positioned Keira in the same way.

I now had Steve stood in front of me and Charlie behind me, both of them had there hands all over my body whilst Steve was kissing me and Charlie was kissing my shoulders and neck, this drove me insane. Then Steve slowly started to unbutton the blouse I was wearing and Charlie began to unzip my skirt from behind. In a matter of seconds I was stripped down to just my lingerie whilst Charlie reached around me and began to stroke my cock. I had to stop him after a couple of minutes as it was to early to make a mess of my new panties. I looked over to where Keira was standing and she was busy sucking away at Tom's cock who was sat on the desk, she'd also been stripped down to her lingeire and her knickers were around her knees whilst Martin was giving her what looked like an amazing rim job judging by the noises she was making and then he began to slip a couple of fingers into her hole to get her nice and ready.

Distracted by the erotic scenes that were taking place on the other side of the room, I was soon brought back to reality when I was pushed over on to the bed so I was now bent at the waist. Steve had stepped to one side and now Charlie had pulled my thong to one side and was beginning to slide his finger into my awaiting asshole which was twitching with excitement. Loud moans from both of us filled the room as we were now being completely dominated by these 4 older gentlemen and I think I can speak for both of us when I say we were loving every minute. Charlie and Tom stepped to the side to have a quick refreshment break but the other two had no intentions for that, Steve quickly picked me up on the bed and placed me on my hands and knees whilst Martin did the same with Keira.

Me and Keira were now face to face, as Martin headed over the bedside table to pick up a condom, me and Keira began to kiss as we waited for what was to come next. Although I received a surprise when Steve decided that he wasn't waiting for a condom and he slowly slipped his cock into my well lubed hole causing me to moan straight into Keira's mouth as we kissed.

'Oh fuck Daddy.... I've missed your cock so much. Please.... fuck.... me..... make.... me.... your..... sissy....' I was trying to talk but it was so difficult with a cock pounding in and out of your hole.

'Oh yeah, you've missed Daddys cock haven't you? Your still as tight as the first time I fucked you, I can't wait to fill your hole with my cum later. Your getting more than one load tonight as well, we'll turn you into a cum loving cock slut by the time you go home tomorrow.' In the meantime, Keira had slipped her underneath me, freed my cock from my thong and was now stroking my rock hard cock slowly. The pre cum was oozing out of my cock soaking the bed sheets below.

Martin had also realised that condoms weren't a necessity and was now slowly entering Keira, she buried her head into the bed sheet, releasing my cock as she struggled to stop herself from screaming out from the pleasure as Martin was now ball deeps in her hole. If there was anyone walking down the corridor or in the adjoining rooms to us, they would have been hearing a hell of a show. Charlie and Tom rejoined us on the bed and slipped themselves in between us, making sure that their cocks were within distance of our mouths so we could suck them off at the same time.

For the first time, I was going to be able to suck Tom's cock while Keira got Charlies. I slowly started teasing the head of Tom's cock before he forced my head down making me swallow him whole and causing me to gag at the same time. On the other side of the bed Keira was slowly licking away at Charlies balls whilst we were still both getting pounded. This went on for about another 10 minutes before Martin and Steve had gotten tired and pulled out of us.

Me and Keira figured it was time for us to do some of the leg work so we swapped positions and quickly mounted ourselves on the cocks we were sucking on. We both got into the reverse cowgirl position so that we could put on a show for the other guys whilst they sat and watched. Taking Tom's cock was going to be difficult, he wasn't much thicker than Steve but he had a lot more girth, Charlie was the same so we both took our time. I slowly started to lower myself onto his big dick, inch by inch it disappeared into my ass until I bottomed out on his dick. Charlie was bigger than Tom so Keira was still working her way down his massive shaft. I let myself settle on Tom's cock and give my booty a little jiggle to try and open myself up a bit more for him. Once we were both settled and ready to go, we both leaned forward placing our hands on the gentlemens shins for balance and then began to bounce up and down making sure to milk the cocks that were inside us trying to push them towards the edge. I then leaned back, placing my hands on his shoulders and continued to ride him, this way our other two friends had a great view of my hard cock bouncing up and down while he fucked me.

Keira meanwhile had lost her dominant position and had been flipped over and was now face down in the bed gripping onto the sheets as Charlie pounded away at her ass. Tom was a much bigger guy than me, and I wanted to try a new position. I wanted him to pick me up and fuck me whilst he pretty much carried me. I got up off the bed, he picked me up, I wrapped my arms around his neck whilst he hooked his arms under the backs of my knees. Luckily Steve was on hand and helped guide Tom's cock back into my ass. And we began to fuck again, it felt so good, I was achieving everything I'd set out. This must be how a woman feels when she's getting fucked. Eventually Tom pressed me against one of the walls and continued to fuck. Back on the bed, and Charlie had increased his pace and was really fucking Keira now, an explosion was imminent.