Mom's Best Friend

Over the next few days, I was able to think about how truly frustrated I was that Kevin couldn't fuck me. It was a rare time in which I felt confident, and I was willing to try it and it all came to a quick stop just like that. After I got past the disappointment, I started wondering whether I should buy some toys, that way I wouldn't have to wait for Kevin and could have something inside me sooner. But I quickly changed my mind on that and decided that I wanted Kevin's cock to be the first thing that goes inside my ass. So, whilst I waited, I realised the best thing to do was to entertain myself by sending Kevin photos of my ass on Snapchat in various positions. He responded by sending me photos of his massive cock until the last one showed me that he'd blown his load all over his own chest.

On Friday evening I was lounging around downstairs after having tea when Mom walked into the living room and said, 'I have a training thing I need to go to next week. I'll be gone from Monday morning and won't get back till Tuesday evening,' it was hard to not smile but I did my best. 'I'm sure you'll be fine overnight won't you.'

'Of course, Mom,' I told her. 'I'll just arrange to meet some friends for food on Monday. I might even have a couple of days off work.'

After Mom left the room, I immediately text Kevin and told him about what Mom was doing next week. I told him I was taking time off work and thought he might like to have me over with a suggestive wink emoji on the end. He quickly responded saying he'd check what annual leave he had with work and would take the same days if he could. An hour or so later he text me again, this time to say that he had his annual leave confirmed and was more than happy to have me over. We thought it might be safer in case my Mom turned up early again. It was easier to get me out of Kevin's rather than him out of my house. Now I just had to get through the weekend. I went shopping online, wanting to impress Kevin when I saw him. I settled on buying a jockstrap and a thong. They turned up on Sunday thanks to next day delivery.

On Monday morning, I was in contact with Kevin, and I said I would text him when Mom was gone and then he would come by and pick me up. Mom left our house at around 11am. Rather than texting Kevin straight away, I thought it would be best if I went upstairs and showered, making sure to clean myself and a chance for a quick shave. It also gave me time to make sure that Mom wasn't going to randomly turn up in case she forgot something. By the time I was out of the shower and ready, wearing my new red jockstrap, I text Kevin to say she was gone, and he could come and get me whenever he wanted. About 20 minutes later, his car was outside, and I was quickly in the passenger seat, and we set off for his house. As we pulled into the driveway at his house, I noticed that he hadn't bothered to open any blinds downstairs.

As we exited the car and walked towards his front door, I couldn't get the smile off my face. It was finally time. I was finally going to lose my virginity after years of waiting and it was most certainly not going to be how I expected to lose my virginity. He turned the key in the lock and stepped aside to let me enter before him. As I stepped foot into his house, he spanked me which made me let out a high-pitched squeal. He closed the door behind him and then pinned me against the wall in the hallway. He kissed me and straight away had his tongue inside my mouth as my eyes closed and my mind drifted away to cloud nine.

'We've got all day,' I said when he broke off the kiss. 'What's the rush.'

'I've waited long enough already, the quicker I break you in, the more fun we can have today, tonight, tomorrow and the future.' He quickly had my t-shirt up around my neck and was now sucking on my nipples and gently biting on them, making sure he got both. I had my head back against the wall, holding my t-shirt with one hand as I moaned. The next time he detached himself from my body, he took me by the hand and led me into his living room which had a sofa, a couple of chairs and a rug in front of a false fireplace.

On the table by the lamp, I noticed a bottle of lube, 'you had no intentions of taking me upstairs, did you?'

'Nope,' he quickly replied. He then fumbled with my shirt to remove it before removing his own, leaving us both in our jeans and socks. We continued kissing with his hands moving all over my body, squeezing my crotch and ass which had me getting more excited. I reached for his crotch and his cock was threatening to rip through his jeans which was a good indication that he wasn't wearing any underwear.

I started unbuttoning his jeans, until I was able to reach into them and pull his cock out. My hand was stroking his cock while we kissed. I was still getting used to the feeling of another man's cock and I was still in awe of the thickness of Kevin's. With my spare hand, I pushed his jeans down until he took over and eventually stepped out of them, taking his socks off with them. I dropped down in front of him, my knees on the hard wood floor which wasn't the most comfortable but that didn't matter whilst his cock was the centre of my attention.

I held the shaft of his cock upwards, so I had easy access to his balls and started with those. I got my head in between his legs as much as I could so I could lick his taint before working my way back over his balls. I took one of them into my mouth and gently sucked on them. Luckily, Kevin shaved his balls but left a little patch of pubic hair just above his cock. My hand was still slowly stroking his cock as I moved onto the other ball and continued sucking. Kevin was moaning and seemed to be struggling to hold his balance as he had one hand resting on top of the fireplace to keep himself upright.

I suggested he moved to one of the chairs, which he did, and he handed me a cushion so I could be more comfortable on my knees. When I was back in position, I moved my mouth over the head of his cock and took the head into my mouth. Kevin moaned straight away as my tongue traced around the tip of his cock and he put his hand on the top of my head to encourage me to go deeper. 'Fuck, you're so good at this,' he kept telling me as I deepthroated his cock again and again until I needed to stop to breathe. Kevin seemed too breathless as well. I then just teased his cock by running my tongue up and down the underside of his shaft.

'Do you want to try a 69?' Kevin asked me as he gathered himself.

'How would that work?' I asked him. I'd seen it in pornos obviously, but I couldn't imagine how two men would do it and comfortably.

He smiled at me, 'I'll lay on my back, and you can sit on my face. Then I can lick your hole while you play with my cock.'

He shuffled himself off the chair and onto the rug, but not before he grabbed the lube and placed it beside him. I stood and turned my back on him and unbuttoned my jeans. I then slowly slid them over my hips and bent over, showing him my ass, which was framed nicely by the jock I was wearing.

'Hmmm, someone's been underwear shopping,' I heard Kevin say. 'I approve.' I stepped out of my jeans, leaving my sports socks on and walked round to the side of his head before slowly lowering myself down so I was sat on his chest. I leant forward and took his cock into my mouth, and it wasn't long before I felt his tongue probing around my exposed ass, my cock still rock hard in the pouch of my jock. At times when I was trying to suck his cock, I just couldn't. The pleasure I was getting from him rimming me was making me moan and I lost all focus other than the sensation in my ass. Whenever he took a break on my ass, I would dive back onto his cock and deepthroat him, feeling the head of his cock rub the back of my throat. Next came the cold sensation of lube as he spread it around my hole before slowly sliding his finger inside me. That amazing feeling from when he did it last time returned, and I was loving it. Every now and then he would slide his hand under my crotch and rub my cock through the material of my jock. I could feel that it was slightly damp from pre cum leakage.

'Do you think you're ready to try my cock?' He asked me as he slipped a second finger into my ass.

'I don't know,' I said as I looked over my shoulder. 'How will it fit?' I stroked it in my hand, still feeling the impressive side of it.

'We'll use lots of lube on your ass and my cock, and I would recommend you ride me first so you can control how much you take at a time,' Kevin was reassuring me, and I trusted him. He placed a generous amount of lube and massaged around my hole and inside me before handing it to me so I could cover his cock.

Once we were ready, I stood above him and moved down so I was standing directly above his cock. Kevin held it straight whilst I lowered myself down. When I was just above his cock, I put one hand out to steady myself and then held Kevin's cock, who then used his free hands to help me balance as well. I felt his cock pushing at the entrance to my hole and pushed out ever so slightly so that the head could pop in past my sphincter.

'Holy fuck,' I almost shouted. 'It feels so fucking big.'

'Just take your time,' Kevin told me, resting his hand on my thigh.

I continued to lower myself down on his thick pole, taking inch by inch. Kevin kept encouraging me, saying things like, 'you're taking my cock so well, normally first timers can't take any of it.' After what felt like an eternity, I finally felt my ass resting against the tops of his legs. I felt so full and the first thing I noticed was that my cock was no longer hard.

'Fuck me,' Kevin moaned. 'Your ass is so fucking tight. Just stay there for a little while and let yourself adjust.'

'I feel so fucking full,' I told him. In my head, I was just thinking; holy shit, I have a fucking dick inside me. I am currently being fucked. The thoughts were running through my mind quicker than The Flash.

After a couple of minutes, I felt ready to move. I was able to reach out and place one hand on the sofa whilst Kevin took my other hand as I slowly started to rise off his dick and then lowered myself back down. Kevin must have noticed that the look on my face wasn't one of total enjoyment, but he encouraged me to keep going, saying that once that initial feeling goes, all I'll be left with is pure pleasure. And he was right. As I found a rhythm of bouncing up and down on his cock, suddenly, pleasure started to flood through my body. And my confidence started to grow, eventually I had both my hands behind me for balance and I was riding his dick a lot quicker. Looking down, I could see my own cock flopping about in my jock. I found it weird how I could be feeling so much pleasure with a soft cock, but I wasn't going to complain.

'Please will you fuck me from behind?' I asked him, feeling ready to try new positions but also out of breath from riding his cock.

'I thought you'd never ask,' Kevin said with a devilish smile on his face as I got up off his cock and moved into position on all fours. This was the first time that I felt like I was submitting to him, and letting him take control. I almost felt vulnerable but excited because I was now going to get properly fucked. Kevin knelt behind me and thrust his cock back into my ass and I let out a long groan before he grabbed my hips and started to drive his cock in and out of me.

'Holy fuck... fuck me... fuck yes... it feels so good... don't stop... please don't stop,' I kept moaning and moaning over and over again. The sound of his body slapping against mine was for some reason turning me on. His hands were really digging into my hips as he kept going.

'Oh yeah,' Kevin said in between breaths. 'You like your Mom's best friend fucking your ass?'

'I fucking love your big cock in my ass.' I said back to him, 'thank you, thank you for fucking me.'

'If only your Mom could see you now,' Kevin laughed. 'Big strong Chrissy on his back, begging for more cock, you don't like being called Chrissy, do you?'

'You can call me whatever you want as long as your dick is in my ass,' I moaned at him. 'And while you're behind me, fucking spank me.'

Kevin laughed loudly, 'holy shit, who thought I'd turn you into a cock slut this quickly,' he said before he slapped my ass which made it sting and probably left a handprint on my cheek. His demeanour then changed; his breathing seemed to increase. 'Fuck, your ass is to fucking tight. I'm gonna cum soon, but I want to see you when I cum deep inside you.'

He slipped his dick out of my ass with a plop and turned me over and onto my back. He held one leg in the air and the other pushed out to the side. The leg he was holding was shaking with pleasure as he lined his cock up with my hole and pushed it back in. I had my hands out to the side, gripping onto whatever I could while I moaned. He was really pounding my ass which was making my leg shake even more. My whole body felt like it was shaking. 'Argghhh fuck... keep fucking me... fill me with your fucking cum... I fucking need it,' I told him.

'Here it comes, fucking take it,' Kevin moaned. He thrust deep inside me and held himself there. I didn't feel much other than a warm feeling deep inside my ass. Kevin continued to grunt through his orgasm until his cock started to soften and eventually slipped out of my ass.

Not trying to ruin the moment, 'should I go shower?' I asked him quickly. 'I don't want to leak all over your rug.'

Kevin laughed, 'it's fine, but shower is at the top of the stairs.' I didn't want any awkward after sex chat, so I ran up the stairs with my hand covering my ass and I could hear Kevin giggling to himself as I did so. I sat on the toilet first and tried to empty out as much cum as I could before jumping in the shower and cleaning myself. Once I was out of the shower, I put my jock and socks back on before heading downstairs. Kevin was in the kitchen, so I put my t-shirt on before he came back with a couple of drinks for us, still completely naked and we sat on the sofa.

'So, how was that?' He asked, eventually breaking the silence.

'Honestly,' I looked at him and watched his face drop like he was expecting some bad news. 'It was amazing,' a broad smile broke out across his face.

'I'm glad to hear it. Were you okay with what I said to you? About your Mom and stuff?'

'Oh yeah, absolutely. To be honest, it turned me on a little bit.' I could see his cock twitching, and, in my head, I couldn't believe that he might be able to get hard again already.

'And you're not bothered that your Mom's best friend loves fucking your ass?'

'Absolutely not, if I was going to experience anything like this, then I'm glad it's with you,' I leaned over and kissed him. 'Plus, we still have all afternoon and evening.'

After that little conversation we had some chill time. Kevin disappeared upstairs and came back in a pair of briefs and a t-shirt. We left the blinds closed downstairs all day so that we didn't have to bother putting pants on. We spent the afternoon watch television, me leaning in close to Kevin and enjoying being all cosy. I fell asleep at one point and woke up on the sofa, to see that it was already getting on for 6.30pm.

'Evening sleepyhead,' I heard Kevin say when he saw me stirring on the sofa. 'I've left a takeaway menu in the kitchen if you want a phone an order in. Just get whatever you like, and I'll pay for it when it turns up. I'm just running upstairs for something.'

In the kitchen I looked over the pizza menu before settling on a couple of different pizzas. I found my phone and rang the number. As I rang the number Kevin appeared in the kitchen, naked from the waist down with his hard cock sticking out in front of him. He walked up behind me and bent me over the kitchen counter, and I felt him applying lube to my ass. Just as he was lining up his cock with my ass, the takeaway answered my phone call.

'Hi, can I put an order in PLEASE?' My voice changing as Kevin pushed his cock back into my ass again. He slowly started pushing in and out again.

'Delivery, please.' He slapped my ass loud enough that the guy on the phone heard. 'Can I have... oh fuck... sorry... fuck... a pepperoni pizza please?'

'Oh yeah, and a meat feast pizza... fuck... please?' I was seriously struggling, and I turned to tell Kevin to stop but he just smiled and kept fucking me. 'Some chips as well please, yes that's every-fuck-thing... thanks.'

I quickly put down the phone which was Kevin's cue to start fucking me harder and faster. Now I was just moaning in tune with his thrusts. 'Fuck, you're like a Duracell bunny,' I told him.

'Yeah, I told you. Once I broke you in, you were going to love it, do you want me to stop?' He asked before he stopped thrusting.

'I didn't say that did I? Keep fucking me, we haven't got long before tea gets here... oh fuck.' Kevin started thrusting again. He lifted one of my legs, so my knee was resting on the top of the kitchen counter, and I was standing on my tippy toes on the other leg. I put my hand out in front of me onto the wall to stop Kevin fucking me through it.

'I fucking love your cock,' I moaned at him. 'I want it every fucking day.'

'Yeah? How do you like my load?' He asked. 'I've got another one ready for you.'

'Fuck yeah, give me it. I want you to fill me again with your fucking load.' Kevin pounded me for the next couple of minutes and I could feel my legs starting to give way underneath me. And just before they collapsed Kevin pushed his second load into my ass again, filling me with that warm sensation again. As his cock fell out of me this time, I collapsed onto the kitchen floor, my legs shaking as I struggled to catch my breath. 'Holy shit,' I said, crumpled in the corner of the kitchen in a mess. 'How did I not know this would feel this good? I haven't even came yet, but I feel like I've had multiple orgasms.'

Kevin was now sat on one of the kitchen chairs, 'Just imagine how good it would feel when you cum with something in your ass.' After I fully recovered, I climbed up off the kitchen floor and cleaned the mess on the floor that had leaked out of my ass. Kevin put me a towel down on the sofa, so I didn't have to shower. When the food turned up, Kevin collected it from the driver, and we ate. We then sat and chatted for most of the night until it started to get late.

'I should get going,' I said, making a move to stand up.

'Why don't you stay?' Kevin asked. 'I could drop you off at home on my way to work tomorrow.'

'I was hoping you'd say that' I said with a big smile on my face before I kissed him. That night, Kevin led me to his bedroom where we spent the night sleeping in the same bed. It had to have been one of the best nights sleep I'd ever had. When I awoke the next morning, Kevin had already left the bed and was somewhere else around the house. I glanced at the clock and saw that it was still early, but I knew Kevin would be getting ready for work and that I'd need to get going soon. I climbed out of bed, feeling sore, sticky, and still extremely horny. I hopped in the shower quickly and freshened myself up. When I was in the shower, I thought about playing with myself and making myself cum, but the horniness inside me took over and I made the executive decision that I needed to be fucked one more time.

I wrapped myself in a towel and wandered off downstairs and looked around but couldn't see him. I looked around every room downstairs and couldn't see anything. Only when I was in the kitchen could I hear a sound coming from outside, most likely in the garage. I quickly ran upstairs and found a pair of shorts, threw them on, grabbed the lube and headed outside towards the garage. It was a warm morning, so I wasn't likely to catch a chill being outside with no t-shirt on. As I walked into the side door of the garage, I could see Kevin was messing around with this tools like he was looking for something. I closed the door behind me, which got his attention.