Babysitting with Robert

**

Week 9 was the week we really talked about me.

I didn't feel at all weird about hanging out with him casually after our talk the week before. Maybe that in itself is weird, but as we drew on the chalkboard with the kids and watched them run circles around each other I found it very easy to separate the two sides of our night.

We seemed to have a routine at this point. We didn't drink all night but as soon as the kids were in bed we would have a glass of the rum he was now keeping at the house for us. Then we would chat about everyday life. He always updated me on sports of course, and then I would tell him about college. It was almost exam time, and then I would have a huge summer off before university.

Then we would seamlessly transition into talking about sex and relationships like it was nothing. I repeated a lot of what I had said a week earlier, talking about how my lack of control was hindering my happiness and all the rest of it. He offered some advice in return, doing the best job he could of helping me out.

He told me that I could eat any boy for breakfast and that I needed to believe that. He wanted to me to regain my confidence in myself and in my sexuality. Take back control of how I behaved and realise that I was never the one who should be chasing a high. As far as he was concerned the boys should be chasing me and it should be for me to only give it up when I wanted to, because he knew for sure that there wasn't a single guy I could want more than they wanted me.

It was a confidence boost and it did make me feel special, but the way you feel can't just change overnight. It was nice though, and it made me happy. As basic as that was it was a constant with him. Every week we learned more about the other and every week I felt better for it.

It had all happened so quickly but it was clear to me now that this was the best part of my week. I spent every day from Sunday onwards excited for it and looking forward to spending time with him, and it was still a surprise to me what a unique bond I had forged with a much older guy. I knew he was a real friend and I knew that he truly cared and I could never shake how special that made me feel.

He left a little early again and for that hour that it was just me, I realised how much I missed having him there.

**

Week 10 was the week I knew I had a stupid crush on him.

It really was stupid. It felt typical of my luck. Of course I had a crush on a guy with whom nothing could happen. Of course the best guy I had connected with in my entire life was a grandfather of five. It was one of life's greatest jokes on me, but at the end of the day it was easy for me to look past it. It was a fleeting crush and nothing that would impact the sweet friendship we had formed. It was just a reaction to recent events. He made me feel cared for and special because that was in his nature.

It would lead to nothing, and that was fine. Feelings come and go. I didn't want to have sex with a 55 year old man anyway. It was just a cruel blow that he was 55 to begin with.

We still enjoyed a good night when the time to babysit came. It was a stop start conversation because young Ryan was feeling sick and couldn't settle and fall asleep for very long at a time. We still fit in some chatter in between each of us heading into his room to check on him, but we only really sank into more mature conversation a couple of times.

He checked in to see if I had been keeping well and I told him this had been one of my better weeks in a while. He told me to keep it up, but that whenever a bad week came upon me, he would still be here on Saturday nights to chat to me about it. He assured me he would be here every week through the good and the bad times.

Before long we were joined by Ryan who was struggling big time, but he caught some sleep in his grandpa's arms. We returned our conversation to less adult topics while he was present, but in the end we needed to cut Cerys and Matthew's night short because their little boy needed them and they were back before it was too late.

**

Week 11 was the week that we really talked about sex.

It was as if we had to make up for the previous week when time was stolen from us. He arrived earlier, and we had the kids in bed nice and early too. Then we spent our time together, laughing and happy.

The primary focus of our night was sex, and that probably wasn't the smartest thing for me to engage in when I fighting off stupid feelings. It came about naturally as so many of our topics did and we slipped into it with so much comfort. I never felt nervous to tell him anything though I did take more joy in talking about his sexual history. I was still finding myself again when it came to my sexuality so sometimes it seemed better not to talk about memories that could have been negative. Instead I pestered him and learned more about his youth.

I found out it had been a couple of years since he gave up dating altogether. His focus moved onto the kid's full time, and he had effectively chosen to give up any chance of being with someone ever again. That was beneficial to me. Not only was my crush ludicrous enough already, but he was retired anyway. I could look beyond it now and just enjoy time with my new friend. We had a relationship that spanned so many important facets of both of our lives. We didn't have to talk about sex and love forever. We could just stay friends and talk about life itself and he would provide me with the same care and attention he had for the last couple of months.

**

Week 12 was the week that I realised I wanted to have sex with him.

Don't our minds work in mysterious ways? One second you've convinced yourself something isn't possible and the next you're willing to risk it all.

I had added Robert on social media a few weeks earlier after we had established our friendship. As our 12th night together approached he messaged me to say he was looking forward to seeing me. He said he looked forward to spending time with me and our time together hanging out and chatting was his favourite time of the week.

Just like that I knew. It just clicked, the cogs started turning. I knew what I wanted and little else mattered. I thought about it a lot, but I felt so sure of myself that I was never attempting to convince myself out of it. I had zero doubt that it was what I truly wanted, and it was something that would make me happy. It was different to everything else that had happened over the last year of my life.

This was me realising I actually wanted to be with someone. This was me making a positive decision for myself while in the right frame of mind. This was me choosing a person because of how much I liked being with them and how much I felt like they respected me. He had helped me build up a new confidence and now it was him I wanted to use that on.

I had no interest in seducing him and acting like my old self. I just planned to tell him my truth and seeing how he took that. He had listened to everything I had said so far so I was convinced he would do that again. Even if he didn't want to do it, he would respect and trust me enough to hear me out.

Picturing sex with him was crazy. I had never experienced anything like that in my life. A much older guy. I had no idea what he would look like and how capable he would be of performing. These doubts were based on a complete lack of knowledge more than anything, but an important element of me now wanting to have sex with him was a growing attraction. He had a thick head of grey hair and kept his face clean shaven. He was huge as well, over a foot bigger than me. He kept in good shape and had told me plenty about his running regime. He was a tall, slim and handsome grey fox and he had started to turn me on. I was well on the way now, and I knew that come Saturday I would tell him.

I was so relieved that the kids were in a good mood that night. I wanted as much time to talk to him as possible. I wanted to pour my heart out and see what he offered me in return. We hung out for a while as normal before I said anything, time I needed to settle some nerves. I never had doubt that I would get scared and not tell him though. I was sure of myself and content with my decision. I told him about the message he sent me first and how happy it made me feel, and then it was time to treat him to the news.

I told him about the positive impact he had had on me, how much happier I had been in recent weeks and how I felt more and more like my old self. I even told him that it had been a while since I had slept with anyone because I wasn't relying on that for gratification anymore. I told him that my feelings for him had grown over the last few weeks and at first it didn't seem real but it was and I had to tell him about it.

I remember scooting down the couch and turning to face him, closing the gap between us. I crossed my legs and spoke so passionately about how I felt and as perplexed as he seemed, he listened to everything I had to say as he always did. I had to convince him that he had helped to fix me and now I knew what I wanted, it was just a weird coincidence that the person I wanted was him.

He told me to wait and see how I felt in the future, but I had done that already. It had been a couple weeks since I had started to feel this way, even if sex only came into the equation over the last few days. He wanted me to do it with the right person and found it hard to believe that was him. So I challenged him to look at me and see if he believed I wanted to fuck him for the sake of it, or because I truly cared about him.

When he finally accepted this is what I wanted, he still found arguments for whether that meant it was the best thing for me to do, or for him to do to me. He was very aware of the age difference and was terrified that he would just be another regret. He didn't want to have the same effect on my wellbeing that the other negative experiences did. He was scared I would wake up the next day and realise that it wasn't what I wanted at all. I couldn't prove what the future would hold, just convince him that I was happy and I wanted to share something special with him because I knew we could have a fun time and it would be just that. Of course we weren't going to get together long term, but we could have one small experience that would mean more to me than everything else I had done in the last year.

"I want to do it with you." I must have said it four or five times. He was taking everything slow, thinking about his responses and taking a breath when he needed it. He laughed or chuckled his way through my rants, and we ended up just giggling about it together. Not taking everything so seriously for a second was a big helper, and after that everything seemed so much easier. The mood lightened and he seemed less desperate to play devil's advocate about the whole thing. I was winning him over.

He asked me if I could truly see myself not regretting this at all because that was his worst fear, and I assured him of that. He laughed again and shook his head. "I didn't expect this at all." he said, and his voice was more strained than usual. He really was shocked by the whole reveal, but it was so cute.

"I know it's a bit weird and out of the blue." I said, leaning in to touch the thigh of his that was just an inch or two from me as I sat facing him on the couch. We had barely moved in what may have been hours. "I didn't know how to tell you at first."

He ran his hand through his hair and cleared his dry mouth with a sip of the hard stuff, gurning at the burn in the back of his throat.

The whole time I wanted it I didn't know how it would happen. It may be a little awkward for him to do it on his daughters couch with the kids upstairs, but as far as I was concerned I wanted it happen there and then. The stairgates would protect us from them and I just expected we could keep extra quiet.

It seems we had agreed to do it without outright saying it, but my hunger for him had been growing for a while and I was desperate to make a real connection with someone again. "Are you okay doing it here?" I asked. It was such a relaxed and surreal conversation to have.

"Tonight?" he said, surprised again.

"If you want to." I was happy to give him the offer and see if he was comfortable, but if it came down to it and he wasn't willing to do it right here then I would have had zero hesitation going back to his house when I was finished for the night.

"Okay." he said, before smiling at me nervously. "I'll try my best."

I giggled and lifted myself up off my bum, ending up on my knees beside him. I leaned in to kiss him excitedly, and he kissed me back. The seal was broken and I could already feel the happiness that it brought me. This is how it was supposed to feel.

We kissed for a quick 15 seconds before I straddled him, sitting in his lap with my knees either side of his legs. Then we kissed and kissed. Minutes passed by with us just kissing. It was what I needed. I loved the affection of the innocent exploration. Just our lips at first, and then our tongues dancing gently. He grew in confidence and brought his hands to my hips and then stroked along my thighs after passing over the fabric of my skirt. I held his face in my hands, wrapped my arms around his neck, pressed my fingers into his chest, it didn't matter. I just loved kissing him and being in his arms and feeling like I was doing the right thing.

I could have kissed him all night, but I could feel his dick pressing against me through his pants and I knew I needed so much more than just his lips. I pressed my hand against him for a second as we broke our kiss, and we giggled into each other's faces as our noses stroked against one another. It was such a foreign feeling to be this excited, and the feeling of him hardening for me sent shivers through my body. I lifted myself up, standing over him so I could push my knickers down my legs, stepping out of them with my right leg and then kicking them off at my left foot onto the couch beside us.

I crouched down back over his lap and undid his pants, and he lifted his bum off the couch so we could push his pants down his legs. I fell back onto my knees as they reached his knees and immediately took hold of his dick to guide it against my opening. I fell further into his lap as it entered me, and it wasn't until I let out a sharp breath that I remembered I needed to keep quiet. I smirked as I moved in to kiss him again, slowly gyrating my hips back and forth against his crotch. We shared a few slow kisses as we breathed into each one, trying to keep the noise under wraps all while sharing in the moment that was so intense for the both of us.

I remember him mumbling a "wow" or two as I pulled back from kissing him and started lifting myself up and down his dick, edging up inch by inch before falling back down until his shaft was engulfed again. I kept it slow at first because I had no idea how long it had been since he had sex and how the body and cock of an older man work, but I edged things up a notch or two each time he kissed me.

He kissed my neck as I rode him and while doing that his hands explored my legs some more before sliding onto my bum. He held a cheek in each hand, squeezing them occasionally. With his hands there to guide me I sped up again, breathing roughly into his hair as he sucked on my neck. When he pulled away we shared one more sloppy kiss before I arched back, putting my hands behind myself and onto his knees which hung off the front of the couch. I rode him harder again, grinding on his dick as he brought his hands to my hips to hold me steady.

We were further apart at this point so I could watch him as I rode him, taking in the little expressions on his face each time my bum slapped back against his thighs. He looked so serious, but that would break every time he looked at me and he smiled. It was the only time he looked a little nervous the entire time we had built up to this moment. After finding a rhythm to ride him with for a few minutes I leaned back in to him, pressing my body against his and kissing him. I felt every inch of his cock slide out of me slowly as I lifted off him.

I took his dick in my hand for a second as I breathed into his cheek, realising for the first time he was circumcised. It was the first time I had handled a dick like that, though I had little clue what difference it made. The second it took me to catch my breath was a quiet one, my hands massaging his dick the only real movement being generated by either of us.

The feeling was almost too much, the intensity of feeling so much emotion tiring my body as much as my mind. I wanted to revel in each moment and appreciate how good I felt and I tried my best to do just that, the feeling of his hand on my lower back such a simple thing but in that moment it made me feel incredible.

I wanted to make him cum. I had no idea if he could go for hours or if his dick was already on the brink of explosion but between the intensity of my feelings and the fear of being caught, a quick and simple hook-up seemed like the best route. When I started thinking about sex with him, this was what I expected. I would fuck him, and then I would use my mouth to make him cum. I wanted that cum so bad. For the first time in a long time I wanted to finish someone and be truly happy about it.

I lifted a leg over his lap and kneeled beside him again, just like I had when we started kissing. With my legs together and bum poking up into the air I leaned forward to take his cock in my mouth. I had both hands around the base at first, propping myself up as I bobbed in a messy circular motion over the head of his cock. Those first swipes of my tongue over the sensitive head generated the most sound out of him, sharp exhalations followed by almost silent inhaling.

I battled with my long black hair, pushing it behind my ear whenever my movement led to it falling over my face. He soon helped me with that, bunching it up in his hand and holding it over the back of my head. I kept licking his dick over and over, bouncing between tongue and then lip focused action at random. The only time I really broke from his dick was to tell him to tell me when it was time. "Tell me when you're coming." I said, and he murmured acknowledgement.

I pushed myself around halfway down his cock as his spare hand roamed down my back. He lifted my skirt a little and stroked the very top of the back of my thigh before his hand slid onto the closest ass cheek he had available. He squeezed it and stroked the skin gently as his breathing intensified again, and then he told me it was time.

"I'm close." he said, and this time it was me mumbling an acknowledgement.

"Mhmm." I forced out, mouth still very full. I quickened my speed, pushing him over the edge and feeling his body start to rock as he came. His hand on my ass squeezed tighter and he let my hair fall loose, letting out a gust of breath he held in as he approached orgasm. He tried his best to keep quiet, but his foot smacked into the ground a couple of times as his body convulsed.

His load hit the roof my mouth pretty hard, and he had quite a bit of cum stored up for me. I started to swallow before he was even finished, drinking his cum with satisfaction. I kept sucking him until he could take no more, bringing his own hand to the base of his dick to pull it from my lips. I sat up with an overwhelming feeling of, basically, 'Oh shit, you just did that.' I really did, and I fucking loved it.

I rested my head on his thigh for a second and we chilled in silence, his dick softening to the side of my head. The way I felt was unique to my recent life but the complete norm when I was around him. I was happy and felt special and there was no chance of regret. I felt satisfied as he told me it was an "amazing surprise."