04 Timothy
THREE MONTHS AGO
The thing I love about my jobs is that most of the time I get to be myself, and doing something I love, sex. I love having clients fuck me or having me fuck them, but besides two regulars I have, escorting is too infrequent. I might get the one or two older men looking to fuck a young piece of ass, but it’s only a one night arrangement and onetime payment. I have to work a few other jobs to supplement my income.
Before you ask, yes I’ve done porn. I only did it for three months, and I did low budget amateur videos, mostly of me jacking off, only one video of me having sex. It wasn’t too different to what I’m used to, but the pay wasn’t what I expected, I decided to work for myself after that.
Now I do cam shows, which pay around the same amount give or take, but since I can work from home I can work as much or as little as I want to. Some days I work from eight to eight. I’m very popular in the Asian time zone, and in the American ones. Now I charge people to watch me whack off, play with my toys or do some of the weird shit they want me to do. I make a decent amount of change from the comfort of my own home, and no one takes a cut.
One night I had been doing a show, being watched by five guys and my tip pot was way over six hundred so I was set for the night. I just finished shooting my load, and ready to log off for the night, when I got a message by someone watching me. They asked me to have a private conversation after I finished. Normally I wouldn’t, but he tipped me a fiver, so I felt like that got him at least a couple minutes.
LL: hello
Ken316: hello
Ken316: I just wanted 2 say I’m a big fan, and im glad your chattin to me
LL: your welcome
Ken316: I’ve watched all of your shows for the last couple nights, & tipped a little, but I was wonderin, r u really in London?
LL: yes, I am
Ken:316 I was wondering if you like to meet me,
LL: sorry I don’t do that cam only
Ken316: oh well I wanted to talk to you as im a virgin & wondered where gay guys go.
LL: how old are you?
Ken316: 15
X X X
I had given it some consideration, and having Tim over for the weekend was going to be a good experience for him. I had realised I’d been putting my own selfish needs before Tim’s. He had asked me because he wanted to get away from his life, and when I was his age I wanted to do the same. Why was I worried, Tim isn’t like Mark for several reasons, but mainly Tim was simple.
I made my way to Tim’s to tell him the good news. I buzzed the door and waited.
‘Hello,’ came Tim’s mother’s voice.
‘Hello it’s L, is Timothy home?’ I ask.
‘He’s here but you’re not coming up.’
‘Okay, can you just tell him I’m here,’ I say, ‘Please,’ I add remembering my manners.
There was no reply as the intercom was hung up. I waited to see if Tim would actually pick up, but instead I saw him coming down the stairs.
‘Hey,’ said Tim, when he came out of the door. ‘Sorry about my mum she’s been in a mood all evening. What are you doing here?’
‘Well I wanted to surprise you,’ I say, ‘which I think I have done and tell you some good news.’
‘Shall we walk then,’ suggests Tim. We start to walk down the street.
‘So I thought I would let you know, we’re going to have a little birthday weekend next week, just like you wanted.’
‘Really,’ says Tim, not sounding the bit excited or enthusiastic.
‘Yeah, you asked I thought about it and I thought why not. Give Tim a birthday he’ll remember.’
‘Well then I guess it can wait till then.’
‘What can?’
‘I was going to see if you wanted to do some stuff today.’
What the fuck!
‘You wanted to have sex?’ I ask, really hoping he was kidding.
‘No,’ he says, slowly, ‘I wanted to ask what is it going to be like. I don’t mean like what happens, I mean like what real sex is really like.’
I take a deep breath before I speak, ‘but why do you want to know? Have you been thinking about it?’
‘I have, well I always have I am a teenager. But I have been thinking lately, what am I waiting for? I mean I could do it right now and it could be as worse or as good if I had it in four months from now, or a year or three. So I think now it’s time to stop thinking and just do it.’
I took in every word Timothy was saying, what surprised me was how much I could relate to what he was saying. It was weird because this was the first time I was thinking about Tim instead of thinking about having my dick in his ass.
‘So when did you want to,’ I ask.
‘I think for my birthday weekend,’ says Tim, ‘but I don’t think I want to rush it. I know we’ve haven’t done a lot of the stuff that builds up to it, maybe we can go from top to bottom.’
‘Puns intended?’
‘Yes, but I do have a lot of questions that I really want to know.’
‘I will answer them all,’ I say, stopping to look at Tim.
‘I’ll write them down and we can talk about before next weekend,’ says Tim, giving off the eager student vibe.
‘Sounds like a plan.’ We continue to walk, and let the comfortable silence between us hang there.
X X X
The pleasure of meeting Mark isn’t what it once was. Our meetings had started to defrost over the last two weeks, but it was clear as day the magic was gone and it was never coming back. When it was time for his first appointment of the week I ready myself for an awkward hour of my time.
‘I don’t want to fuck today,’ says Mark, when I close the door behind him.
‘Oh,’ I say, floored by his announcement. ‘What do you want to do?’
‘I wanted to talk,’ says Mark, ‘ever since… we really haven’t been ourselves, and I want you to know I don’t hate you.’
‘Okay,’ I say, knowing better not to jump in.
‘At first I was mad at you, then I slowly realised I was mad at myself, because I had fallen for someone I shouldn’t have. I’ve done some thinking, and it affects you to. We need to pull back from each other. For now we’re going back to once a week, and I don’t want you to see Julia anymore.’
I looked at him wide eyed. He was right, he was affecting me, I was now losing out on money, and I was losing the hottest sex I’ve had with a man over forty five. The Julia thing was something I was looking forward too, as I am past done with her, but I was genuinely sad about losing Mark.
‘If that’s your choice,’ I say, trying not to sound like the money grabbing whore I am. ‘Is today going to be your only visit?’
‘I think that’s best, and one the reasons why I want to talk to you and not fuck you. I want to see what kind of man I am when I haven’t fucked you because I honestly don’t remember. So today we’re going to talk.’
‘Okay,’ I say, having no idea what we’re going to talk about for an hour.
THREE MONTHS AGO
After talking to this fan for a few days I finally felt a little certain he wasn’t having me on, so I went about to chatting to him a different way. We mostly exchanged messages about his questions on what it was like to be a confident gay man. He asked if I did actually enjoy sex with men, or if I did it solely for the money. I answered his questions, because there was a naivety to them, which I felt if this was someone trying to honey trap me, they were certainly doing a good job of it.
Eventually I asked him for his number, and he was more than eager to give it to me, but I wasn’t interested in speaking to him through text messages. The minute he gave me the number, I called him through my throw away sim card to have a conversation with him. The phone rang a couple times before he answered.
‘Hello its LL,’ I said, when he answered.
‘Hi it errr,’ he said, and his voice didn’t sound too deep, but it did sound young. ‘Ken right?’
‘You should know, it’s your name isn’t it?’
‘Not really, I kinda forget what names I use where.’
‘Why do you use a different name?’
‘I don’t want to be spotted by any one I know.’
‘That makes sense,’ I said, ‘but you need to be a little more consistent with the names. So what is your name?’
‘Tim,’ he said, steadily, ‘What yours?’
‘You already know mine, its L.’
‘What does the L stand for?’
‘I’ll tell you that if we meet face to face.’
‘Seems fair I guess,’ said Tim, then there’s a silence. ‘I err want you to know, I am really am new to this whole thing.’
‘What whole thing?’ I asked, curious to know what he meant.
‘Having sex with another boy, I’ve wanted to for a long time. Well I thought about it for a long time. I mean I’ve liked boys for a long time, I mean when I think about it, I think I was in love with my best friend when I was like nine, but I didn’t know what it meant. Now I do, and I’m okay with it.’
‘And how do you parents feel about that?’
‘Well err I haven’t told them…yet. I will soon though.’
‘No need to rush, if you want to tell them you can tell them. It’s your choice.’
‘I know, but I really want them to know, but I’m not sure when I want them to know the real me. I mean my parents of devoiced, and I’d like them both to know me, you know, but I kinda feel like it would be nice for me to say, mum I’m gay and this my boyfriend. So she doesn’t think it’s a phase or that I’m doing it for attention.’
‘Okay that makes sense,’ I said, realising this kid has some brains. ‘So how come you haven’t had sex yet?’
‘That’s, well… a tricky one, and a long story.’
‘I like long stories, and I’ve got time.’
X X X
With Timothy’s visit only three days away, I was in a panic about how I could make this special weekend very special. I need a cake of course, then there is the gift I think I have got it, but there is the one thing I’m missing. I think I’m worrying a bit too much about the sex, which is weird I never worry about sex.
I am worried because this the first time I actually had notice I was going to be fucking a virgin. Usually they tell me when they’re getting naked, or I’m sucking on their cock. Of course then it turns me on so much I can’t wait to fuck there ass. This time I’ve known a while and I’ve wanted it so much. The thing is this time is he is very much one hundred percent a virgin. I will be his first for everything, and when I think back to mine it sure was different.
I remember all my firsts, the first time someone sucked me, when I sucked someone, got fucked and fucked someone. They all were different people. But for Timothy I'm going to be that guy, he’s going to remember me always, and unlike before where I didn’t know the guys it didn’t really matter. This time it mattered to me. I need to be on top form, and I need to not be my distant self. I need to be there and be present, so his first time is something he doesn’t regret like I do some of mine.
Before I go out and spend a load on the perfect de-virgining weekend, I need to work first. I was spending four hours with my longest regular client Richard, who was in need of me as he hand seen me for almost two months. I liked Richard as he was a handsome man, and ridiculously over paid for my company. Unlike Mark he knew what I was and since he was a business man he knew this was all business.
‘How’s business for you?’ asked Richard, after I finish sucking his cock.
‘Not great, but I think I need to move into a different area of the sex industry. Maybe I should stop selling myself, and start selling others.’
‘You want to be a pimp?’
‘Couldn’t hurt, or try and be the porn king of north London.’
‘Well whatever you decide let me know I’ll invest.’
‘You’d invest in my porn or pimping agency?’
‘Of course, I mean you and I have been meeting for two years, and I come back cos I like that you can be frank about your work and you’re worth the money. If you’re getting out of it I want to be there to help you get to the next part. But of course you’d have to fuck me for free as I'm backing the business.’
‘Well of course all investors are entitled to free head.’
‘That’s all I ask,’ says Richard, kissing me, ‘but honestly if you’re bored and want a real job I can hook you up.’
‘I’ll remember that, but for now I’ll stick to being my own boss.’
‘Well for another two and half hours I’m the boss’
X X X
Since it has been such a while since I’ve seen Richard I had forgot what it was like to just hang with a client and not entertain them. I had gotten used to doing everything for guys I’ve always been calling the shots or suggesting the shots and that’s what I need to do with Tim this weekend, just have him over and let him decided if he wants to fuck, or when he wants. Of course I’ll give him a rundown of stuff that’s on the menu this weekend.
I told Tim to meet in Soho on Thursday evening so we can discuss what is on the menu. When I got to the coffee shop I saw Tim there early.
‘Am I late?’ I ask, sliding into the seat opposite Timothy.
‘No I’m early,’ said Tim, ‘I really wanted to know what you couldn’t tell me on the phone.’
‘Well I wanted to tell you about sex since I’ve read your questions, and I’m going to answer them before the weekend, so you can make an informed decision about it.’
‘We’re going to talk here? Why could we do this at your place?’
‘Because if we did it at my place it would be too easy for me to tell you what’s what and then jump into it. What I’m going to tell you, you might know or you might think you know because sex is a serious business, and I want you to take note of what I say and when you come over on Saturday I want you to know all your options and make your own decisions.’
‘What you’re saying is I get to choose.’
‘Yes it’s all up to you, it’s your first time not mine. I want you to have all the power.’
‘What if I say you choose, you will?’
‘Nope,’ I say, ‘you choose everything the power is yours.’
‘Wow that’s kinda scary,’ says Tim, ‘I thought we would just go with your lead.’
‘I know, but you’re making an adult decision and it’s time for you to follow through with it.’
‘Okay,’ says Tim, showing signs of worry.
‘Right well, gay sex where to begin,’ I start, feeling like the world’s most fucked up teacher. ‘Well it is enjoy able if you do it right. Porn, TV and movies portray it as a simple as bending over and sticking your dick in a hole. It is that easy if want to cause pain. Or want your partner’s hole to bleed.
‘Sex is a messy business, in more than one way. You always want to be clean and showered. You want to make sure you wash your balls, your ass and clean under your foreskin, because that can be nasty. Now if you’re going to bottom you gonna want to douche.
‘What’s that?’ Tim interrupts.
‘It’s the cleaning of your rectum to make sure it’s clean free and ready for action. Yes it’s messy, but believe me it’s better than the alternative. I call of that the prep, and once that’s done its down to the fun.
‘You can start out with some kissing, it’s good to helps build tension, it can go on as long or as short as you want. However, some guys don’t kiss because they think its gay, but willing to shove yourself in a guy’s ass isn’t gay, so there fucking idiots. During the kissing you can move your hands around to get a feel build more tension. While you’re kissing clothes can come off or stay on, just depends on the person again.
‘After kissing most people usually move onto oral. Most sexual health people say to have safe sex your need to have oral with a condom, you can, but unless you like sucking on latex, it’s not the same. Never suck after brushing your teeth cos there is a risk if you do without a condom. Depending on how much you want to suck is your choice and how long the guy can hold his load. If he does cum and cums in your mouth it’s your choice if you want to spit of swallow, but the first couple of times the feeling of cum will be weird in your mouth.
‘Now let’s move on to the main event anal. First of all it isn’t everyone’s bag, some guys don’t like it because of the mess, and some don’t like it because of the pain and some like it because of the former and the latter. But for you, I want you to be sensible, if you like it you like it, and if it hurts you and don’t like it don’t force yourself to do it because a guy wants to. If you want to stop tell them, because sex is about pleasure, but some find pleasure in the pain, but I'm jumping ahead. Bottom line if the pain is too bad stop.
‘To have nice safe anal sex you need to make sure you prep the hole. The best methods for this are rimming and fingering. I personally like to have my hole rimmed or rim a guy before I fuck, because it relaxes the muscles. To help get a better experience you can use flavoured lube, or just go without your choice.
‘Then you’ll want to take some lube and put a little bit on your finger, then slowly rub it over the hole, and then slowly put a tip in and then gently play with the hole as this will help loosen things up. After a minute or two, you could introduce another finger or two just to get the hole ready.
‘After you’ve done all that, it’s time for penetration. Always use a condom on people you don’t know, and even some you do. Just be safe when your starting out okay, don’t want you to get anything. After you’ve done that use lube, a lot of lube. On your dick, on the guys’ hole, there is never such a thing as too much lube. You want everything to be nice wet and slippery, then you put it in.
‘Never forget about positioning, find the best for you and your partner, it’s different for everyone, height and body sizes play a big part so make sure you try to get it right. Then you fuck, you can go fast or slow, but I suggest you go slowly otherwise you’ll bust a nut so quick. When you’re ready to shoot do it were ever you like, or where they ask, but do try to let them know you’re gonna squirt. And that’s gay anal sex.’
There’s a silence, I let Tim take it all in.
‘That was a lot of information,’ says Tim, after a few minutes, ‘You’ve really got sex down to a routine.’
‘Like I say that is the basic set up I do, of course there are some more steps. Some get missed or you mix it up.’
‘I see,’ says Tim.
‘Now I you’ve got something to think about.’
TWO MONTH AGO
This was nuts, but why was I doing it? Well because I'm a little curious. Timothy had asked to meet me, but I had insisted on some where public, as I wanted witnesses, and also to make sure I wasn’t being had. I have no interest in meeting this guy for sex and I have never given him the impression I had. The internet was a murky place.
Timothy asked to meet me some where close to home, as he wanted to be safe in his environment, which I understood. It was Saturday afternoon, so no dodgy during school meetings. Of course I had seen a picture of him, but until I saw him in person I didn’t know if the two people were the same. Of course I was a little exposed and not in a good way. Whoever he was he had seen me many times and had seen me a lot.
As I reached the destination I had no idea where I should be looking. I didn’t know why I was being so paranoid. I just was. Maybe because I had a strong feeling this boy wasn’t a boy at all. I had to be being had, yet the idea that he was real was keeping me on the spot.
As I looked down at the time, I felt someone tap me on the shoulder. I turned around and standing in front of me was the boy I had seen a picture of. He was still a little small, slim, quite the bit pale, short cropped brown hair, and a pair of glasses. This was Timothy.
‘Hi,’ he said, rather sheepishly.
‘Hi,’ I said, just as nervous as he was. ‘Timothy I presume?’
‘Yeah that’s me.’
‘Well you do look like your picture.’
‘Thanks,’ he said, looking at his shoes, ‘you look better in person.’
‘Thanks,’ I said, ‘so did you come here with anyone?’
‘My mum,’ he said, still looking down.
‘Wait what?’
‘Well I kinda told I was gay this morning, and when she said it was a phase I said I was meeting my boyfriend and umm now you’re here.’
What the fuck was going on? Was this a trap? Fight of flight that was the question now.
‘Why would you say that?’ I asked.
‘I panicked and I didn’t know what else to do. I remember what we said about and since we we’re meeting, but I never thought she’d come’
Before I could come up with an answer I noticed a woman coming towards us. She was a little Hispanic woman, with long dark hair.
‘You must be Timothy’s friend,’ she said, not introducing herself.
‘Yes I guess I am,’ I said, still taken back by her bluntness. ‘I guess it’s nice to meet you.’
‘So are you the one that convinced my son he is gay?’
‘I didn’t convince him at all, he approached me and he is either gay or not, it’s just the way he is.’
‘I don’t like you.’
‘I don’t need you to like me; I want you to love your son for who is and not blame anyone for it.’
‘Fine,’ she said, she then turned to Timothy, ‘We’re going home.’ Then she grabbed him and pulled him down the road.
‘Tim I’ll call you later,’ I called, before not knowing why I had said it.
X X X
Saturday had arrived and was fully prepared to have Tim over. To be honest I was nervous and horny. From today I could fuck Tim all day long and it was no longer an issue, and given that he was a horny teenager, and I was like a horny teenager we could be have sex so many time this weekend, the prospects where great.
However, I do need to remember the last time I was expected a shag filled weekend I only got half of what I expected. So I am hoping that Timothy didn’t let down his generation. The condoms were stocked, the lube was ready and this weekend was going to be a virgins wet dream.
Tim had only been to my place once before, and I think the novelty of him being him would take full effect during his stay.
‘Today we are celebrating Timothy’s sweet sixteenth birthday,’ when I open the door to Timothy, with party poppers and happy birthday playing. ‘You can legally bang dudes and do some other stuff I'm forgetting. But for now just enjoy your birthday.’
‘This really wasn’t what I was expecting,’ says Tim, smiling widely.
‘What did you mum do?’ I asks, taking Tim’s bag from him.
‘Just gave me a card, she didn’t seem too bothered.’
‘Well lucky you have me, I am bothered and this weekend is whatever you want to do, or whatever we can get away with.’
‘Could I have you walk around naked?’
‘In theory yes, but not right now, because we’ve got cake to eat and bubbly to drink.’
‘Did you make me a cake?’
‘Oh god no I can’t bake cakes, I just got a small one to have.’
‘L you are the best,’ says Tim, giving me a hug.
We had some of the cake, and then Tim wanted to chill and enjoy his bucks fizz, his first legal-ish drink. Which I was happy with, it was all creating a nice mood to make the events even better.
‘What are we having for dinner?’ asks Tim, casually.
‘What do you want?’ I ask.
‘Pizza?’
‘Pizza it is,’ I say following through on all my promises.
Sometime later I order an extra-large pizza with everything on it, since Timothy couldn’t choose. The talk was causal, and informative to a degree, but the more I listened; I could tell all the talk was a stall tactic. I had the strongest feeling that he felt like me, horny and nervous. I didn’t want to push him in that direction, but I feel I need to at least introduce the idea.
‘What do you think about what I told you the other day?’ I ask, when Tim was chewing away.
‘I looked up a lot of the stuff you said too. You know those sex shows on TV they said a lot of the stuff that you said. So I feel like I’m fully informed. Then I watched some porn and saw they don’t do like you said. I want to have sex, but I want to top first.’
I was surprised and not surprised at the same time.
‘That’s cool,’ I say, to show it hasn’t fazed me.
‘But I err would like to wash and stuff first.’
‘We can do it together if you like.’
‘I didn’t think of that.’
‘It’s a good thing to suggest making sure you both are clean.’
‘What about the bum washing part?’
‘I do it every morning, so I’m good.’
‘Oh,’ says Tim surprised, ‘so shall we go now?’
‘Okay then,’ I say. I walk over to Tim and grab his hand and walk him into the bathroom. I start the shower, and while I’m doing so I start to undress. I know he’s looking at me, because he’s finally seeing me in person. Once I’m naked I step into the shower. ‘Join me once you’re ready.’ I just let the water wash over me, I look to see Tim get slowly undressed and he is keeping himself bent over. He joins me in the shower, and I notice he is keeping his hands in front of his crotch. ‘Want to get in?’ I step to the side so that he can get under the water. ‘Tim you know it’s okay if you’ve got a hard on.’
‘It’s embarrassing we haven’t even touched and I might..’ he trails off.
‘Well this only proves you do like men.’
‘I guess.’
‘Tim just remember were too guys, who like guys so don’t be embarrassed, so turn around and let me see.’
I know this may come as a shock but I have never touched his cock let alone seen it. This was going to be the point when I find out if waiting had really been worth it.
He turns around slowly and moves his hand and I'm very shocked. His cock is massive. Giving my professional eye he’s a good seven inches, but fuck me is his girth thick. Holly shit it was worth it.
‘Damn,’ I say, ‘you’ve been holding out on me.’
‘It doesn’t look small.’
‘Tim if you’re small I'm tiny. I’m not going to lie it’s going to be challenge.’
After we wash up, I help dry Tim off before we go into the bed room, where it’s time to see if I can take all of Tim.
‘I know you told me what we should be doing can we skip a couple things?’ asks Tim.
‘If you want to,’ I say, ‘what did you want to skip?’
‘The blow jobs, I don’t think I can handle it, well taking that is. I don’t think I can do the rimming thing. It seems too weird.’
‘So you want to jump right into the main event?’
I take out a condom and the bottle of lube and hand them to Tim. ‘Okay then let’s dive right in then.’
‘But you said,’ starts Tim, ‘I thought you would…’
‘Force you to go slow? Tim it’s all up to you, and it seems like you like any other man you just want to fuck, so let’s fuck. I assume you know how to put on a condom.’
‘Yes.’
‘Great,’ I say, taking the lube from him and putting on a large amount into my hand, as Tim struggles to put the condom on. Once he’s done I put half the lube on his rubbered boner. ‘Now rub it on.’ He does as he’s told, then I take the rest of the lube rub it on my hole. ‘So how do you want to fuck me?’
‘I don’t know,’ says Tim, sounding extremely nervous.
‘Okay lay down,’ I tell him, and he does, ‘since you’re new to this I'm gonna help you out.’
I know I said I wasn’t going to take control, but I feel that he needs this guidance. Once I start he’ll calm down and take over.
With Timothy lying down his dick is pointing straight up; I straddle him placing his dick right in front of my ass. I then grab hold of Tim, and find my hole using the tip of his cock. When I find it I let it sit there for a couple seconds so Tim can get used to himself being there. I then force myself back a little more, so I can feel the tip of Tim’s dick go in. I manoeuvre myself so that Tim is inside of me, then I slowly lower myself taking in all of Tim’s girth and length till I finally feel myself filled.
‘How does that feel,’ I ask.
‘Weird, but a good weird,’ says Tim.
‘Well congrats boy now you’re a man.’
Without giving any warning I lift my ass up Tim’s shaft, and the back down again, and I hear Tim gasp and I do it again.
‘You like that?’
‘Yes,’ says Tim, through closed eyes and clenched teeth, as I ride him a couple more times ‘I don’t know how long I can…fuck.’
I suddenly feel my inside warm up and feel something expand inside me. Just like that Timothy’s first time is over.
‘It’s okay,’ I say, to be encouraging.
‘NO it’s not!’ shouts Tim. ‘That was only like a minute. I’m so embarrassed.’
‘Don’t be,’ I say, as I slowly climb off him seeing the jizz filled condom. ‘Believe me that’s how the first time is for guys.’
‘You’re just trying to make me feel better that wasn’t good. How could it be, it was so short.’
‘Well Tim mine was like yours, no more than two minutes. It was just so exciting. Anyone who says otherwise is either extremely lucky or a liar and I know where my money is. After a while it will get better and go longer, but that takes time. But I don’t know why you worrying we have a whole weekend to do it like twenty times. No need to be sad.’
‘I knew I shouldn’t have skipped stuff.’
The rest of the night was me and Tim talking about how to last longer at sex. He had no interest in trying again that night, even though multiple time I saw him get hard. Instead Tim decided he wanted to go back to beginning and go slow, real slow. We kissed, we sucked, I rimmed, and he fingered. It was all done nice and slow and it was a pleasant experience. During the course of our play, Tim came another two times.
In the morning I decided to take Tim out for some breakfast, as we sat and ate he didn’t look like a happy boy who just got laid. He looked the saddest I’d ever seen him. I think his ego and expectations had taken a serious shot.
‘Happy birthday again,’ I say, handing him his gift, once we got back in the flat.
Tim takes the gift from me, and unwraps it, once he sees it’s a shoe box he opens it and looks shocked.
‘What is this?’ he asks.
‘It’s the Timothy Morales anal starter kit, complete with, travel size lube, a box of condoms, anal douche and of course small dildo. I thought you could use this when you’re at home so you can get some practice in before you ready to take the plunge.’
‘I don’t believe this,’ says Tim.
‘Well do you like it?’
‘I really do, but what if I wanted to bottom last night what would you have done?’
‘Given it you then, so you could’ve prepared.’
‘You know you have given me an idea,’ says Tim, sounding more like Tim again.
‘Oh yeah?’
‘Since I’m no good at the fucking, I think I’m might use your birthday gift’
Yes, come on Tim give me that virgin ass, time to show you how you lose your v card properly.
‘Do you want me to show you how to use it?’ I ask.
‘I think I know how a dildo works,’ says Tim.
‘Wait what?’
‘I’m going to use the dildo on you, I think that will be fun. And I know you’ve got more I’ve seen the shows.’
‘You’re gonna fuck me with dildos?’
‘Yeah, and I'm gonna fuck you good this time.’
I can honestly say I didn’t see this coming, but he better fuck me good.
