Mom's Best Friend

Growing up a single child was weird for me and no, it's not because I'm from the Northeast of England. Not only was I a single child, but I also only ever had my Mom in my life. I was now 23 and my Mom had me when she was relatively young at 21, meaning she was now 44. She worked extremely hard. When I started secondary school at 13, she went back to college and trained to become a nurse. She now put in a lot of hours every week and would work some weird shift patterns which I'd never be able to deal with. When my Mom told my so-called Dad that she was pregnant, he bolted and was never seen again until a few years ago. He tried to contact me after my 18th birthday, but I politely told him to fuck off. I was always my Mom's priority growing up and she'd never had another man in her life since my Dad walked out on her. Yeah, she had moments where she would go out with friends and bring somebody home. And when she brought those people home, I'm not ashamed to say I stroked my dick to the sounds of her being fucked.

As I got older, I always thought I was a little bit different to everybody else, but I couldn't seem to figure out why. At 23, I was still a virgin and had never had a girlfriend and to be honest, I wasn't really that bothered. I didn't have a massive group of friends so they couldn't take the piss out of me for it, and I never told anybody anyway. Whenever we were talking about sex, I'd just play it off like I'd done it and I was an expert. My friendship group got a lot smaller when we turned 18. A lot of my friends were only interested in going out, getting drunk and taking drugs. That wasn't me and it never would be. I tended to get on better with older people, so enjoyed the company of people at work and whenever my Moms friends come round.

I was also quite feminine growing up. I liked to look good, and I thought I did. I was just over 6ft tall, slim, and played football a lot, so I was in good shape. My hair always had to be perfect, and I was always using all different hair products to make that happen. I had my ears pierced, would only wear designer clothes, and had to be wearing the best shoes on the market. I loved to smell good as well and would always be spending money on the best aftershaves. Underneath the clothes, I thought my body looked good. I hated to see hair on my torso or pubic area so would often shave my chest, balls, and ass. For underwear, I hated wearing boxer shorts. The thought of my cock bouncing around made me uncomfortable, so I'd always wear tight briefs. I didn't have the biggest cock in the world by any stretch of the imagination, but I was more of a shower. I was always around 4 or 5 inches when flaccid and then a thick 7 inches when fully erect.

From 18, I started to masturbate a lot. Usually once a day, maybe twice on a weekend depending on how horny I was feeling. I downloaded lots of porn and had quite the collection but as I started to get older, my taste in porn started to change dramatically. I started off watching lesbian porn which helped me feel manly. Then I moved on to more traditional kind of porn, which found me watching the women more than the men and thinking about how much fun it looked like they have from being pleasured by a cock. Then I found one of my favourite ever porn stars, Daisy Taylor. She is incredible and I loved watching her getting fucked. The way she stayed hard was so hot and so I started watching more and more trans porn. That led me down a dark path to the 'gay' category online and it immediately had me questioning my own sexuality. I quickly shrugged it off and went back to watching normal and lesbian porn.

'Hey Chrissy,' my Mom shouted me. I hated it when she called me that but she's the only one I'd let get away with it. 'Can you come down here please?'

I trudged downstairs, and Mom was sat in the living room with a cup of tea in her hand. A lot of my friends used to tell me that she was a MILF when we were in school. She had big tits, long blonde hair and worked out at the gym three times a week so had an ass that matched that. 'What's up Mom?' I asked her, sitting myself down on the sofa.

'Are you okay sweetie?' She looked a little concerned. 'You seem to spend a lot of time on your own and I just wanted to check in with you.'

'I'm fine Mom,' I told her abruptly.

'You never go out anymore, look at the weather out there. It's gorgeous, yet all you do is go to work, come home, and play video games,' she quickly responded.

'And?' I was sick of this conversation, we had it at least once every two weeks.

'Don't you ever want to meet anybody?' Mom got more and more frustrated every time we had this talk.

'I'm not bothered.' I tried to get up and walk away.

'You know it's okay if you're gay?' She said, hanging on the word gay for a long time.

'I'm not gay,' I shouted before I got up and headed back up to my room.

I barely spoke to my Mom for the rest of the day, and I spent the evening on my own. She went out with her friends, and by the time she got back on the night, I was already asleep in bed. The next morning, I was up and about early for my Sunday league football match. I was dressed and out of the house before Mom got out of bed, and by the time I got home from football. As I was heading out to my car, I noticed another car parked outside our house and quickly realised it must've been Kevin's.

Kevin was my Mom's best friend. They grew up at school together and had now known each other for 40+ years. Kevin was openly gay. He was married early in his 30s, but his husband sadly passed away just a few years later. Since then, he'd not been in another relationship and had stayed single. He seemed happy though. I'd known him since I was growing up and kind of thought of him as a fake Uncle. We got on well and we always had a daft laugh when he was about. He was a little taller than me, had grey hair, a beard which was darker and was a bit of a gym freak himself and had always been involved in sport. In the summer he was always wearing tank tops and showing off his muscles that were underneath.

At football, I couldn't finish the match. A nasty tackle early in the second half ended my game when my knee started to swell up. I had to come off, I couldn't run but was still able to walk. A quick check over by one of my teammates and he told me it wasn't anything serious and I should be able to recover with some ice and rest. By the time I made it home, Mom's car had gone but Kevin's was still outside. I walked into the kitchen and there was note on the table, 'Kevin is coming for car this afternoon, I'll be home late tonight, there's food in the fridge.' I went upstairs and got showered. I threw on a pair of shorts; I didn't bother with underwear purely for comfort reasons and a t-shirt and made myself comfortable on the sofa. I had my leg elevated with a bag of frozen peas covering my knee.

About an hour or so later, there was a knock on the door. I hobbled towards the door and opened it to see Kevin standing there with his usual smile on his face. It was a warm Sunday afternoon, so he just had his tank top, running shorts and a pair of sliders on. He lived about 15 minutes away by car, but must've walked as you could see tiny beads of sweat on his forehead.

'Hey kid, how you doing?' He asked as I stepped aside and invited him in.

'I've had better Sundays,' I laughed as I followed him into the living room. 'Can I get you a drink?'

'A glass of water would be lovely,' he said as he took a seat on the chair, and I began hobbling into the kitchen. 'What have you been doing?'

'Classic football injury,' I shouted from the kitchen. 'Knees a little stiff but apparently I'll be fine in a couple of days.'

I walked back into the living room with the drinks in my hand and handed him his drink before taking my place on the sofa again and elevating my leg again to try and stop the swelling. When I'd been sitting for a while, it tended to go stiff again which would make walking more fun. I chatted with Kevin for a while, I didn't expect him to stick around for this long but there was no sign of him leaving anytime soon. After a little while, I needed to use the bathroom. I slowly climbed from the sofa, limped to our downstairs toilet, and took a leak. And then slowly, I walked back to the sofa, barely able to bend my knee because it'd stiffened up.

'Do you want me to take a look at that?' Kevin said pointing at my knee. 'I might not be a physiotherapist, but I know enough about sports injuries and might be able to help with a little rub down.'

'I mean, if you think it will help, I don't see any harm in trying,' I said, trying not to feel awkward about someone I'd known for so long massaging my leg.

Kevin moved over from his chair and got down on one knee by the side of the sofa. He put both hands around the side of my knee and started to twist it from left to right and then got me to bend it and pull it towards my body before extending it again. 'Is there any pain when I do that?'

'No,' I said, wincing a little bit but there wasn't enough pain for it to be anything serious.

'Well, that's a good sign, at least you haven't severely damaged any ligaments or anything like that.' He continued to play around with my knee until he was satisfied, I wasn't in too much pain. He then proceeded to massage just below my knee, he claimed it was to help with the blood flow and should eventually help with the swelling. Kevin's hands then started to work their way above my knee and around my thigh and hamstring. He was certainly right about it increasing blood flow because I could feel my cock starting to stir in my shorts.

Not wearing underwear was now starting to look like a big mistake. As my cock started to stiffen, I shifted my mind to anything but the massage and tried to stop myself getting an erection, but it wasn't working. Blood was rushing through my cock, and I was now fully erect underneath my shorts, so I made a grab for a cushion and placed it across my crotch. It was only after I did it, that I realised just how obvious that made it look.

'You okay kid?' Kevin asked me, noticing me fidgeting about underneath his touch.

'Yeah, yeah. I'm fine,' I managed to quickly stutter out. I tried to forget about my erection, and just tilted my head back and tried to relax as much as possible. That was the only way to get this to calm down right now.

'That cushion isn't covering anything you know?' Kevin laughed. 'Has it been a while?'

I blushed, 'depends on how long you think a while is.'

'A couple of months maybe?' Kevin looked up at me.

I must've been redder than a tomato now. 'I'd say it's more like years...'

Kevin stopped massaging my leg and looked directly into my eyes. 'No, you must be joking, are you, yeah, you know...'

Before Kevin had chance to finish, I beat him to it. 'Yes,' I said quickly before looking away in embarrassment.

'A good-looking lad like you has never had sex. The world must've gone mad. It must be by choice?' It felt like he was trying to boost my ego.

'I suppose it is partly. I've never really tried to get with a women,' I told him. 'Plus, I'm not sure if it's what I want.'

Kevin looked confused and even I wasn't 100% certain on what I was trying to tell him. I was already extremely aroused, so I was fully blaming my dick for controlling my mouth. The kink I had watching gay porn was always older/younger relationships and the older men tended to be silver haired foxes.

'I don't want this to sound weird or that I'm being creepy but, it seems like you need to care of that problem in your pants, and if you're unsure of what you want, maybe I can help?'

I don't know who was more shocked by that statement, me because Kevin said it, or Kevin for saying it himself. How do I respond to that? My Mom's best friend is currently kneeling beside me, offering to get me off and I've known him since I was younger. Could I let him, do it? Would he want something from me in return? Whilst I was going through all these questions in my head, Kevin's hand started to move further up my leg until he was running the inside of my groin beneath my shorts. His fingers gently tickled the side of my balls, and it caused me to jerk a little bit and I let out an involuntary groan.

'I think that tells me all I need to hear, but I'll ask again, would you like me to help out?' Kevin looked at me whilst he held his hand high on my leg.

My cock controlled my brain and body again as I nodded and told him I wanted him to help. Kevin smiled at me before moving both his hands to the waistband of my shorts. He hooked his fingers into either side and started to try and tug them down. I had to lift my ass slightly off the sofa so he could pull them down and leave them resting around my thighs. My hairless cock sprung out along with my balls and landed against my stomach.

'Fuck,' Kevin said. 'Look at the size of that thing and so smooth as well.' Why was I so turned on by this? Kevin reached for my cock and took it into his hand and gently started to stroke my shaft. I couldn't help but moan. It was the first time somebody else was touching my cock. Embarrassingly I was struggling to hold on already just from Kevin slowly stroking my cock. I started to squirm underneath him.

'You're not going to last long, are you?' He taunted me which was turning me on even more. 'I bet if I even put your cock anywhere near my mouth, you'd explode, wouldn't you?'

'Fuck,' I mumbled as he slowly started to increase his pace. 'I can already feel it building.'

Kevin just laughed. With his free hand he gently started to knead my balls and play with them. He then removed his other hand, leaving me even more frustrated. All I wanted to do was cum, but it seemed like Kevin was enjoying this. He then spit on his spare hand and wiped his saliva around my dick before starting to stroke it again. 'Are you going to cum for me? You're going to cum for me, aren't you?'

'Fuck yes,' I moaned at him. 'You're going to make me cum, please don't stop.' I pulled my shirt up so my load wouldn't cover my shirt.

'I know what will tip you over the edge,' Kevin smirked at me. He then licked his fingers on the hand that had been playing with my balls and moved it to the head of my cock. He then rubbed the head of my cock quickly and the sensation was too much for me.

'Ohhhhh fuck, I'm cumming. I'm going to cum.' Cum erupted from my cock like a volcano, covering my stomach as it just kept on flying out of my cock as Kevin milked me dry. He continued to slowly stroke my cock until there was nothing more coming out. I was breathing heavily as warm cum covered my body.

'Let me get you some tissue,' Kevin said as he got up and walked to the toilet before returning with a wad of toilet paper in his hand. I wiped myself down before pulling my shorts up and Kevin kindly took the tissue and flushed it down the toilet. 'I hope that helped with whatever you might be feeling,' he said as a car pulled into the driveway.

Mom came through the front door and joined us in the front room. Kevin was sitting back in his chair, and I was still on the sofa as she walked in. 'Oh, for god's sake Chris, what have you done now?'

'I'm fine Mom,' I told her. 'It's just a knock, it should be fine in a couple of days.'

'Are you sure? You look a little flushed,' she asked with genuine concern on her face.

'Don't worry about it Kelly, I've given it a quick look. It's probably just a minor sprain, he'll be back on his feet and back on the pitch in a few days,' Kevin stepped in as I stuttered in response to her saying I looked flushed.

I found it within myself to get up from the sofa and hobble my way upstairs to my room. And now, I had a lot to think about. That night I went to bed very confused about what I wanted. Every time I closed my eyes and tried to sleep, images of Kevin playing with my cock filled my mind and I started to get hard again. The only way I was going to get some sleep was to take care of the problem between my legs. I quickly jacked myself off until I came again and eventually, I drifted off. Jerking off didn't help my dreams. I woke up a hot mess in the middle of the night after dreaming of Kevin fucking me. I was on my back, him thrusting away between my legs as I moaned in pleasure.

I spent a lot of time over the next few days watching gay porn again. I joined forum sites anonymously and asked people what I should do about my confused sexuality. Most people told me to take the plunge and some of them were telling me that if I was going to, then it needed to be with someone I trusted.

A week went by, and I heard nothing from Kevin and to be honest, I avoided him whenever he would visit Mom. I made sure to always stay upstairs, and even took on some extra hours at work, so I was out of the house more. What happened between us was still weighing heavy on my mind, but I knew I wouldn't be able to avoid him forever. Next weekend was my Mom's birthday and she'd arranged to have all her friends come to our house for food and drinks, and then they would go out later. I tried to get into work that day, but I wasn't needed.

By the time her party came around, I was completely back on my feet now. Thankfully, it wasn't a serious injury, and I was able to get back into some light gym work. I was downstairs dressed in just a pair of shorts and t-shirt when most of the guests start to arrive. Kevin was one of the last to get here. As soon as he seen me, he smiled and wandered over. He wrapped his arm around my waist and pulled me closer to him, 'how you doing kid? How's that knee?' He asked me, acting like nothing had happened.

'Yeah, good.' I suddenly started to feel nervous.

But so far, I had nothing to worry about. He quickly left me alone and mingled with my Mom's other friends. I stayed downstairs in the kitchen and helped keep things tidy and fetched drinks whenever somebody wanted anything. I watched on as bottles of wine kept disappearing into the recycle bin. And seen as though there was only 5 of them drinking it, it was even more impressive how much they were getting through. Kevin was taking it a lot slower, only getting through half as many beers compared to the number of glasses of wine the women were getting through.

'CHRIS!!!, can you get some more wine from the garage please?' I heard my Mom shout through from the living room. 'Bring plenty,' she then laughed.

'Don't worry, I'll give him a hand,' I heard Kevin say as I walked out the back door and towards the garage that was joined on to the side of the house. I panicked and tried to grab as many bottles as I could from the fridge, but before I could even get the door open, Kevin appeared behind me.

'Why do I get the feeling that you're avoiding me?' He said, standing in the doorway.

'I'm not,' I stuttered.

He walked into the garage and walked directly towards me. I froze on the spot, unsure of where to go or what to do. He got as close as he could to me before he sat on the work bench that we had in the garage.

'Have you thought anymore about what happened last time we were in each other's company?' He looked at me with a smirk.

I had to lie to him, I couldn't tell him that I'd been thinking about it non-stop, and I was now more confused than ever about what I wanted sexually. 'Not really,' I managed to move further down the bench before he moved his hand on top of mine.

'Oh, come on, I'm sorry,' he said with a little chuckle. 'I genuinely just want to help you; I could tell you were slightly confused, and I bet me jerking you off didn't help.'

I shot him a quick look to tell him to keep his voice down as my Mom and her friends were just in the living room and any of them could be wandering into the kitchen. 'Honestly, I don't know what I want,' I told him.

'Do you think you might be gay?' He asked tentatively.