Chapter 6

The Saturday morning started as usual, swimming lesson the full workout and I have to say that I am improving in all areas. This time Luke did thumb fuck me and make me cum in the pool before watching me cum again on the exercise bike. There was just one oldish man in the workout room at the same time and he did nothing but stare at me as I did my routine.

It was driving lesson time again and I had another 4 hours without even thinking that Dave might be trying to see my pussy.

After a quick nap to unwind from the intensity of the lesson it was down to the leisure centre for my 30 minute routine. Karen was on and we had a little chat during which she warned me that there were again some boisterous youths in the pool. I told her that I didn’t intend to use the pool but maybe the jacuzzi or sauna after my workout.

Jason Looked please to see me and he came round my routine with me, watching me and recording my progress on each machine. How he’d record my orgasm on the exercise bike I just didn’t know, I couldn’t imagine there being a box on the computer system for them to enter if a girl had cum or not.

After Jason had watched me cumming on the exercise bike again, I told him that I thought that I might be getting addicted to orgasms as I was wanting to have one all the time.

“That sounds like a good thing to me.” Jason said.

“Well it’s certainly fun at the moment but I guess that there must be times that it can be a problem, especially if the start coming spontaneously.”

“You mean like when you’re talking to someone like your bank manager and you suddenly cum?”

“Yes.”

“Are you like that?”

“No, it’s just that I want to cum most of the time and when I do it’s not long before I want to cum again.”

“I would have thought that that was a good thing not a bad thing.”

“Well it is at the moment but who knows what that damned drug did to me. It might have sown the seeds for me becoming a nymphomaniac.”

“You should be so lucky.”

Also whilst we were going round Jason asked me about the picnic and I told him that Karen had almost forced me to go with them without any clothes on. Jason smiled and replied,

“I know, she told me, she also told me that you’d thoroughly enjoyed yourself and wanted to go on a day trip to the seaside, and to walk along the sea front amusements and the funfair all whilst naked.”

“She said that! I don’t remember saying that. I’m sure that I’d get arrested if I did that.”

“Probably not, it depends which resort we take you to. If it’s one of the big ones there will probably be lots of yobs there and lots of coppers to try to keep them in line, but the smaller resorts are quieter and you usually never see a copper so I’m sure you could get away with it.”

“Do you think that I should try something like that Jason?”

“You already have and from what I’ve heard you had an amazing time and got an admirer as well.”

“Who?”

“Matt, and from what I’ve heard he’s quite keen on you, do you fancy him?”

“Yes, I think that I do but I’m sure that he wouldn’t want to go out with a girl that looks like he is babysitting. Besides, I’m not sure that I want a boyfriend at the moment, just a friend with benefits.”

“Time will tell Penny, but I guess that it’s all down to how affectionate you would get in public, if you were canoodling in public someone might complain but if you were just holding hands people would probably think that it was sweet for him to be holding his little sister’s hand.”

“Where did you get the word canoodling from Jason, do people still use that word?”

“Well I just did and you know what I mean.”

By then we were getting to the end of my routine and I was in the standing splits when Jason looked at my spread pussy and said,

“And I’m 100% sure that Matt would like to fuck that.”

“You think so Jason.”

“No, I know so, that is every man’s wet dream.”

“Do you dream about my pussy Jason?”

“Yes, but you mustn’t tell my girlfriend.”

“I won’t, thank you for telling me, maybe you should find a different way to support me in the swimming pool.”

“Nice as it sounds Penny, I don’t think that that’s a good idea.”

“Probably not, I guess we’ll just have to stick with thumbs.”

My 30 minute routine was complete and I headed for the jacuzzi. Karen had been right there was 3 boisterous youths in the pool but when they saw the naked girl walking alongside the pool they shut up and watched me. Then they followed me into the jacuzzi.

I guess that it was very similar to the previous week with them saying things and me ignoring them, then me sitting on the side with my knees open and practising my Kegel exercises. I was glad that they had the common sense not to try anything because I would have screamed blue murder and got them thrown out of the hotel.

When I left them they didn’t follow me and guessed that they didn’t want everyone to know that they had boners.

Back in my room it was a shower then some more theory test practice until I started to feel hungry. My pussy was starting to tingle in the anticipation that it would me Matt that delivered my room service meal.

It was Matt that brought me my burger and fries and after he’d put them on the side he turned to me and said,

“Can we talk please Penny?”

Basically we told each other that we liked each other a lot and that we wanted to get to know each other better. Not necessarily as a couple but as good friends, Matt adding ‘friends with benefits’ to which I agreed. I was acutely aware of the problems that would face both of us if we became a ‘couple’ and I got the impression that Matt did as well so friends with benefits would be good for both of us and we agreed to go forward on that basis and see how things went.

“So how do we start the ‘with benefits’ part?” Matt asked.

“I think that you already have Matt. You’ve already seen me naked, you’ve already made me cum, you’ve seen the videos and you know that I am still a cock virgin. I can also tell you that I’ve never given a blowjob and never had my pussy eaten. I’ve never even had a cock in my hands”

“And you want me to help you with those problems Penny.”

“Yes please, but there’s another problem that I’m hoping that you can help me with, I want to resolve those problems live on a camgirl session.

Matt’s response was to say,

“I can’t right now, I’m supposed to be working, I’ll probably get a bollocking for taking so long to deliver your burger.”

I smiled, reached over and kissed him on his lips and replied,

“What time do you finish.”

“Midnight.”

“I’ll be expecting you at midnight then. Oh Matt, there’s one more thing that I think that you should be aware of, I think that I’m becoming addicted to orgasms.”

“Well Penny, that’s something else that I look forward to helping you with. I’ll see you at midnight.”

Like a love-stuck teenage girl I ate my burger, cleaned my teeth and showered. I cursed myself for not getting any nail varnish then thought,

“Nail varnish, like makeup, will make me look older than what I look like without it, Do I want to look half my real age or a little bit older? If I look at bit older will people start complaining about me being naked so do I really want to get some nail varnish?”

In the end I decided that I would get some but only use it on the occasions where I wanted to look as close to my real age as possible. I had this vision of Matt taking me to a posh dinner and dance and me wanting to look like a woman of the age that I actually am.

I didn’t see any point in putting any clothes on because Matt had seen me naked a lot. I couldn’t ever remember seeing him when I had any clothes on. Apart from that I was hoping that he would take my cock virginity live on my camgirl site and definitely wanted to be naked for that.

I was ready for him hours before he was due so I decided to take my mind off what I hoped was going to happen by doing some more theory driving test simulations.

The next thing that I knew was someone knocking on my door. It was dark outside and all the light were on. I was half way to the door when I realised that that I must have fallen asleep and that it must be Matt knocking on my door.

It was. I let him in then excused myself and went to the bathroom where I splashed some water on my face. As I properly woke up my pussy started tingling in anticipation.

“So Matt, this is it, do you still want to do this for me, do you still want to take my virginity live on my camgirl site?”

Matt pointed to the large bulge in his jeans and said,

“Does that answer your question Penny?

I licked my lips and smiled.

“So how are we going to do this Penny? I’m guessing that you want your first cock penetration to be the star of the show, that is to say you want the camera to see me entering you?”

“I do.”

“So the best way that I can think of doing it is for me to get on my back with the laptop between my legs like you did in your videos, then for you to stand either side of my hips and then lower yourself onto me. Does that sound okay to you?”

“Yeah that’s the only way that I could think of doing it as well. Every other way would block the view of the camera.”

“That’s decided then,” Matt said, “but first come here Penny.”

I stepped to him and he put his arms round my waist and kissed me, a proper kiss, tongues and all.

That was the first proper kiss that I had ever had and I wanted it to go on for ever, well almost, there was another first that I had to take care of.

As we kissed I started to undo Matt’s jeans and with a bit of help from him he was soon as naked as I was, his warm, hard cock pressing just below my ribs.

I soo wanted to grab hold of that cock and hold it and kiss it but before that I wanted it inside me.

My first orgasm with a cock inside me was starting to make its presence known but I had to stop. I pushed myself away from Matt and pulled him down onto the bed and arranged his legs and the laptop between them so that his balls and cock filled the screen.

“Before we do it live can I just look at and hold your cock please Matt? I’ve never seen one properly before.”

Matt wasn’t going to object and he just lay there as I explored his genitals with my eyes and fingers. I was aware of the fact that when a man hasn’t had sex for a while it doesn’t take much for them to explode so I didn’t want to touch him too much. There would be plenty of time for that later. My priority was to lose my cock virginity.

I straddled him sitting on his thighs with his cock pressing against the crack of my butt.

Next I leant forwards and started my camgirl session. Once we were streaming live I announced that as promised I was going to loose my cock virginity live during that session.

The comments started coming in and I waited for a couple of minutes for the count of voyeurs to top 100.

“Right, here we go.” I said and raised myself up.

Matt’s cock came on the screen as my pussy went right up to the top of the screen. My right hand went for his cock and held it up upright and I manoeuvred myself until I felt the tip of his cock at the entrance to my vagina.

Three things happened then in this order. Firstly I nearly orgasmed at the feeling of Matt’s cock touching my entrance, secondly I soo wanted to just go down on him as fast as I could, and thirdly I slowly descended enjoying every millimetre that Matt’s cock went into me. I have never had such a wonderful feeling, another thing that I wanted to go on for ever and ever.

I was totally oblivious to the camgirl session as I descended. Even when I couldn’t go any further down and then I started going up and down I didn’t even remember the laptop.

I didn’t stop going up and down even when I felt him cum inside me which triggered me to cum.

It was only when Matt’s cock started to go soft that I bottomed out and just sat there that I looked at the laptop.

Oh my gawd, the comments were coming in faster than I could read them. Then I shut that laptop lid, got to my feet, turned round and lay on top of Matt, my mouth finding his.

After a kiss that lasted for hour (maybe 2 minutes) I lifted my head and said,

“Thank you Matt. I have wanted to do that for ages.”

“You are so welcome Penny, I’ve wanted to do that ever since I first walked into this room and saw you naked for that first time.”

“Can I explore your body please Matt?”

“You don’t need to ask Penny, you can do whatever you want with my body, whenever you want.”

“And you can do the same with mine Matt.”

I shuffled down Matt’s body until my face was millimetres from his cock. It was still soft but it was covered with both his cum and my juices. I studied it and started playing with it with my fingers marvelling how it grew and pointed towards the wall above Matt’s head.

I wrapped my hand around it and instinctively moved my hand up and down slowly. I kissed then licked the tip and tasted both the near clear liquid coming out of the end and both of our juices that were left from us fucking earlier.

I couldn’t help myself and before I realised what I was doing I was straddling Matt again and going up and down on his cock. It didn’t take long for us both to cum again then I collapsed down onto Matt again. After getting my breath back I slid off him and lay next to him on my side with an arm over him.

The last thing that I remember about that night was me thinking that my pussy felt wetter than it ever had before.

I woke to the feeling of Matt fucking me again. I was on my back with my legs spread wide and Matt was on top of me supporting his weight on his arms. My pussy was responding quite fast and before long we were both cumming. Matt rolled onto his side and I had just thanked him when I realised that it was starting to get light outside.

“Shit, what time is it Matt?”

“6:45 why?”

“I’ve got my swimming lesson and workout at 7 a.m.”

“Oh yes, a thumb fucking from Jason or Luke.”

“Yes, you’re not going to get all jealous on me are you Matt?”

“Hell no, friends with benefits not lovers.”

“Yes that’s right, so if you want to fuck Karen or whoever I don’t expect you to not do it because of me.”

“Karen wouldn’t want me and there’s no one else at the moment.”

By then I was in the bathroom sat on the toilet.

“I wouldn’t be too sure about Karen.”

“So what are you doing today Penny?”

“Swimming lesson, workout, hey you could join me there, then breakfast then a driving lesson. Then I’ve got them every Monday, Wednesday and Friday until I pass my test. Oh, and I’ve got my theory test on Tuesday. I need to revise for that today and tomorrow morning as well.”

“You could save some time by getting a room service breakfast Penny. It won’t be me bringing it because I’m not on until this afternoon but I’m sure that one of the other guys will appreciate seeing you like that.”

“That’s not a bad idea Matt.”

“Do you want me to phone the order through? What time for?”

“9:15 please.”

“Consider it done Penny. Hey, I hope that you didn’t mind me waking you like that?”

“Hell no.” I mumbled as I cleaned my teeth.

Matt was on the phone when I came out of the bathroom. I looked at my vibrator and thought,

“Shall I, shan’t I?”

I decided against putting it in me, thinking that I didn’t want it in for my driving lesson and there’d be plenty of time once I’d passed my driving tests.

My breakfast was ordered and I said,

“Are you coming to watch me do my workout then Matt?”

“Rain cheque? Tomorrow? I’ll have more time tomorrow morning.”

“So will I, okay, tomorrow it is. Gotta go.”

I grabbed my key card and as I walked to the door I said,

“Shut the door when you leave please, Seeya at midnight?”

“Midnight it is.” Matt replied.

Karen was walking along the downstairs corridor at the same time as I was and when she saw me she said,

“You’re looking cheerful this morning Penny.”

“Yes I am, I lost my virginity a few hours ago.”

“Good for you, who with?”

“Matt.”

“I sort of expected that, was it good?”

“Amazing.”

“So you two will be at it like rabbits from now on?”

“Maybe, we’re not going to be boyfriend and girlfriend, I don’t think that either fair on him or that I’m ready for something like that, we’re just going to be friends with benefits.”

“So you will be going at it like rabbits then.”

“I hope so.”

Karen unlocked the door and I went to the pool ready for my lesson.

I was sat on the side of the pool dangling my feet in the water when Jason came and congratulated me.

“Is nothing a secret in this place?” I asked as I lay on my back ready to practise how my arms and legs should move.

“Not really, especially when you tell Karen something and you go making videos of yourself doing things.” Jason replied as he grabbed my ankles and started moving my legs like I should for the breast stroke.