Damn It!

"Sounds good. What did you have in mind?" Anna asked cheerfully.

"Well, I thought since we were here, why not start with a swim?" I replied looking over at the crystal-clear water.

"Sounds like fun. Want to make it interesting?" Anna asked with a cheeky smirk.

I knew that smirk.

"What are you thinking?" I replied staring at her.

"Topless," Anna said smiling.

I wasn't about to say no.

"Easy for me. Why not," I said getting up from the chair.

"I knew you'd say that and maybe," Anna said standing up and moving beside me from the other side of the table. "Maybe we can skinny dip after dark..."

She pulled her shirt over her head, dropped it on the chair and then reached behind undoing her bikini top. She handed it to me, keeping her arm over her breasts for a moment before she pushed her shorts down with her other hand and walked to the water. Seeing her only wearing the bikini bottoms was quite intoxicating and with her sensual walk to the pool I was keen to join in.

"I'm game if you are," I said watching while she turned to face me and dropped her arm. Her tits were free and I couldn't help but stare.

With a cheeky grin, Anna turned, making sure I was looking when she stepped down into the pool and then dove in. It was a sensual sight to say the least and I felt myself fill with joy and happiness.

She popped up in the middle of the pool, looking stunning with her wet hair falling over her shoulders.

"Coming in? The water is fantastic," Anna said cheerfully.

I didn't waste any time, removing my shirt and heading into the water in my board shorts. I can honestly say it was easy and fun, with us swimming around for hours until the sun went down. There wasn't any pressure, just two people enjoying each other's company for once. Yes, we did end up skinny dipping and it was enjoyable to finally see her completely naked. She liked my piercings and showed me a couple of her own. Anna even suggested getting her nipples pierced and wanted me to go with her. I simply told her to let me know when and I would go along. After all, what was wrong with two friends having some fun together?

Chapter 15

It happened to me one morning. I woke up and just lay there in bed when this thought and feeling overtook me. I felt energized for the first time since Heather's betrayal came out. I wanted to get out there and live life again, I wanted to be free and get moving. It was Josephine and I that had many discussions and long talks about all of it for months. She kept telling me to get back out there, to move on and put it all behind me. Just two days prior, Josie got angry at me and told me to get on with life because I wasn't young any more. I had never heard her speak that way to me and it flicked some kind of switch. I guess some of it finally sank in. It had been a year since Heather died and we all knew it was time.

It also meant I wanted to feel fit and healthy once more. Not that I had let myself go so much; it was more that I wanted to put more effort in. So, I did what anyone with a personal assistant does. I got her to schedule in my mornings so I could work out before work. The only problem was, Carly and Josephine wanted to do it with me. Given everything that had happened and the fact they were two of my most trusted people in my life, I agreed. That and they brought up those two words no guy likes to hear when there is nothing wrong with them; 'I'm fat.' Yep, Carly said that when I ask her to schedule gym time, and boy did she mean it. There was no way this woman was fat; I just couldn't see it. Perhaps my definition of fat is different to hers?

There we were, at the company gym, me in my running shorts and t-shirt, towel in one hand, water bottle in the other when Josephine and Carly walked up wearing the tightest active wear imaginable. The last thing I wanted to be was distracted. Damn it!

"Ready?" Josephine asked throwing her towel over her shoulder and walking ahead to the treadmills. This woman was the embodiment of motherly comfort but by the grace of some higher power did she make working out look good. I knew her husband was a lucky man and he was grateful for his wife. I had heard that comment a few times over the years we had been working together and he never let me forget it. I understood where he was coming from and I never let it get to me, he just loved his wife that much it seemed.

We had agreed to a routine of warming up first on the treadmills, then some bike work, then weights and a cool down of stretching on the mats. We'd alternate days for different areas of the body, but the routine would be the same.

"Sure thing," I said before Carly smiled and walked in front of me to one of the treadmills. She put her towel over the handle, water bottle in the holder and as I was doing the same, she pulled her leggings up, doing that little dance where they are working their hips side to side, while pulling upwards. I had a hard time looking away from her ass as it jiggled and the seam pulled into the cleft of her buttocks.

I know it sounds so dumb, but I was really noticing how thick Carly's ass and legs were. The curves of her cheeks, the flair of her hips and then the way her waist curved in. Not much skin was on display, but from what I could see underneath the gaps in her crop top, she had blemish free skin up her spine and boy did her back look good. While she didn't have the widest hips, she still had a nice curve to them, but with a thick, round ass that led down to some seriously toned thighs. I tried not to stare and when she turned, I think she caught me, that little smile of hers giving it away. I wasn't even going to dare look at her chest, which seemed rather large in that tight top. Compared to Josephine she was medium to large, but then again, anyone except Olivia would look smaller against Josephine.

"Well, here goes," I said trying to distract myself away from the two women next to me. I jumped on the treadmill and went for it. Getting into the zone.

Next thing I knew, we were doing some weights on the machines and then stretching. All of us were sweating profusely and it felt invigorating to be active again. We did chat throughout the workout but I tried to keep my eye level up as they looked amazing all sweaty. I know what you're thinking but women always look good wet and this was no different. Carly in particular had this dark patch between her tits which highlighted them further. What? I was a lonely man, leave me alone.

We hit the locker rooms, got showered and dressed before heading for the office. That was our new routine and I couldn't have been happier.

Chapter 16

Time had flown now that I was back in the saddle, so to speak. It was getting easier to move on from the hurt of losing Heather, and there were still times I missed her, but everyone around me had allowed me to live again. There was only one thing missing, but I wasn't about to push the intimacy thinking it would be best to let it happen organically. The preceding year had been one I'd rather forget in some respects but it also went by fairly quickly. That's what I've been telling myself anyway.

I was in good shape; the dad bod had receded and some definition had started to re-appear. Anna had noticed and complimented me on it at various times throughout my journey back to fitness. I mean she had nothing to worry about given she looked great all the time, and I let her know that too, given it didn't feel right to be the only one receiving praise. I guess it brought us closer together and there were some glances at times, touches and even some longer hugs. Even during our nightly swims or should I say skinny dipping sessions, we found ourselves gravitating towards one another and our bodies pressed up against each other.

I guess that's why we ended up sitting close together on the sofa, bodies touching while trying to watch a movie, when Anna took the remote and turned the TV off. I looked at her and she quickly started.

"John, we need to talk," Anna said which made my ears prick up. That could only mean one thing and I was hoping it wasn't what I was starting to think.

"About?" I asked giving her my full attention now that things seemed serious. I felt her fidget slightly before she took a quick breath. It must be something big.

"Us."

I stared at her a moment waiting for the rest but she seemed to hesitate.

"Okay, what about us?" I asked trying to figure out what she was trying to say. She looked at me and then gave me a small, comforting smile. Her hand reached mine, squeezed it and then let go. I knew that move, it usually meant she was comforting me around something bad. I took a breath and waited. I didn't have to wait long.

"Contrary to popular belief I am a private person. I know I've let my hair down at times, but only with those I trust deeply... and I know I went a little silly after Mark died, but that wasn't me. I will keep what's between us private," Anna said which was comforting. I knew what she meant; I could understand the need to act out a bit. Thankfully I was over that now.

"I know. I appreciate it," I said touching her knee. She smiled at that and I was about to say something else but she continued.

"Good. With that in mind, I wanted to ask you something. Something personal," Anna said staring at me intently. I knew right then it was big, she was waiting for any reaction just in case.

"Sure, you know you can. Shoot."

"Okay," Anna said and I could see a moment of doubt and nerves. She stood up and began to pace a bit before stopping in front of me. I was looking up at her, those beautiful eyes when she continued. "I was wondering if you'd like to become... a friend with benefits."

The nerves hit her hard right then and I could tell it took a lot for her to ask me. I quickly stood and put both hands on her upper arms, making sure I made eye contact. I wasn't against it, that's for sure, she was attractive and vibrant. It's just that I wasn't completely sure how I'd feel even though it had been a long time since Heather had passed.

"I don't know and I mean that from the point of view that," I said grabbing her hand to try and calm her fears. I could tell she was starting to freak out a bit, it took a lot for her to ask. "I'm not sure how I'd feel after, if you know what I mean. I find you very attractive and I think's it's obvious from some of our swims that I would like to hands down, sleep with you... I do love you, you know that, but, if I'm being honest... I'm a little scared that it'll feel like I've done something against Heather."

I know that was a little weird given Heather had cheated on me, but it is the truth. I focused on Anna and the way she relaxed spoke volumes. She had been so accommodating with me and wonderful that I couldn't help but feel privileged to know her. Anna had been great and I needed to give back as well, not that she would expect or demand it.

"I get it. I do, and I'm only asking to try. I'm not about to demand anything. This is purely because I feel we both have needs and, well, I trust you. So why not take advantage of that mutual situation we find ourselves in? I'm not going to make you feel bad. I'm here for you, and we can take as much time as you need," Anna said which was lovely and wonderful to hear.

"Thank you," I said smiling at her. Her nerves seemed to go and the happiness return. "I don't want to hurt you. Believe me and yes, I do trust you too."

That brought at tear to her eyes. She quickly wiped them away and nodded.

"Sorry," Anna said with that light chuckle people do when trying to compose themselves.

"Don't apologize, it's okay," I said pulling her to me for a hug.

It was warm and wonderful to hug her, with her pulling back to look at me.

"This doesn't mean we have to be super serious or anything. I'm not wanting to get married again, I had the love of my life, so I'm not asking for a commitment, just a chance to scratch an itch so to speak. You know, so we can help each other out at times," Anna said giving me a look that meant business.

"I know, I understand completely and I'm not asking for commitment either," I said pulling her face to me but she stopped me right there. I could see she was anxious again.

"Please don't hate me, but can we just not kiss to start with?" Anna asked nervously and I could tell she was trying to smooth everything over. It was quite endearing actually. "Like you said about Heather, for me it's Mark, and maybe it's because we've been friends for so long... but... I don't want to push that envelope yet. Is that okay?"

It was a relief that she wanted to not get too personal.

"Of course. Let's stay comfortable. I'm glad you said it," I replied clutching her hand. "One step at a time. It'll help me get back on this horse."

"Thank you. It really means a lot," Anna said with a smile. "God, I hope I didn't screw anything up then."

"Why would you?" I asked quickly. "Can we just make sure we talk through it and sort out any issues? I'd appreciate that. It'll help us be comfortable with one another..."

"I appreciate that too. Thank you," Anna replied kissing my cheek. "We've both lost a lot and I'm sure you'll agree that we're not trying to replace them. Just dip our toes back into the water, so to speak..."

I smiled and knew exactly what she meant. It was hard not to compare to someone you had been with for a long time, but still it was out of mutual respect we put the past behind us.

"I wouldn't have it any other way," I said feeling her relax more.

"I mean, we have seen each other naked, right?" Anna asked with a smirk. She was indeed correct, the number of times we skinny dipped at night in recent memory, was more times than I could count on one hand.

"Yes, we have," I replied with a happy nod. "And I should have said this sooner... you are gorgeous..."

Anna blushed and squeezed my hand.

"Likewise. You're very handsome," Anna said getting all girly on me. "Shall we?"

"Why not," I said taking her hand and heading to the bedroom. She smiled and nodded slowly while biting her bottom lip. "Now that we have that out of the way, how about we have some fun?"

Anna put her arm around my waist and pulled me to her, slowing our movement to the bedroom but allowing us to explore each other with our hands.

"I like the sound of that. What did you have in mind?" Anna asked before we got to the bedroom door. "Before you answer." Anna got close to my ear and whispered, "I hope it's okay to say it, but I am really horny..."

I felt my arousal lurch forward and my old friend stir down below.

"I see. Well let's see if we can do something about that," I said happily. "No pressure, but when you whisper it makes it sound so much naughtier."

I got a grin from her and then she moved back to my ear again.

"Good, because my pussy is soaking wet," Anna said in a whisper. "God, I want you to fuck me..."

We sauntered into my bedroom and then I had the worst thought imaginable. It had been so long since I had been with anyone else that I forgot all about protection. She could sense my hesitation.

"Umm," I said trying to think quick. This couldn't be happening, could it?

"What is it?" Anna asked seeing me worry. I could tell she was trying to make this as comfortable as possible for me.

"I, ah... don't have any condoms," I said seeing her smile brightly.

"John, honey," Anna said warmly. "I've been tested and I don't have anything other than a needy sex drive. I know you don't have anything..."

"Oh, it's not that. I haven't had the snip," I said looking at her, but again she beamed almost giggling with how stupid I must have sounded.

"Is that all?" Anna said with a giggle before pulling me towards the bed. "Believe me when I say this. That's what makes this even hotter..."

"Really?" I asked looking at her smoulder while shaking her head ever so sexily. "You're not worried?"

"Not one bit, I love it raw," Anna replied going straight for my pants to get me out of them. "I should warn you now. I love it when a man explodes inside me."

I was flabbergasted and speechless. My pants and underwear were in her hands before I knew it and she folded them before putting them on the chair in the corner. I couldn't do anything other than remove my shirt and throw it away. She just giggled again and began undressing herself. I know, not very polite of me, but I stared like it was the first time seeing something new. The way her body moved and constricted throughout the process.

"Wow," I said swallowing hard.

While I wasn't kidding when I said Anna and Heather could be twins, there were some differences. Anna was different and in only good ways. I looked at her hips, those wonderful hips that had birthed two children and I was in awe. She had a triangle of close-cropped pubic hair, which seemed to be pointing the way to glory, above her otherwise bare pussy. Anna saw me staring and for a moment I heard doubt in her voice.

"Not too shabby for my age, huh?" Anna asked which threw me for a curve ball. Here was a woman in her late thirties, making that comment and she looked incredible. Barely a hint that she had kids, with a trim figure and she was unsure of herself. It wasn't that way when we swam together, I had to put her mind at ease. "You're pretty hot, my god..." No one had ever asked me that or said that before.

I looked up at her and smiled which soothed her concern.

"My god you're sexy. You have no idea," I replied happily. "I was just admiring how beautiful you are."

The way her face lit up at my response quashed any remaining doubts. I looked back down at her pussy, her huge clitoris between those beautiful lips. It was going to be wonderful to suck on and to pleasure Anna. Hopefully my skills would win her over. But she had other ideas.

"Now since this is our first time, how about I crawl onto the bed and you take me doggy?" Anna asked with a sexy grin.

I cleared my throat, again my brain not registering because I was in awe of how Anna took control while being completely naked. It didn't seem odd and I wasn't nervous at all.

"I've never had to ask this before, but are you okay with my piercings and," I asked but she moved closer and pushed her naked body against mine. It felt so amazing to have a warm feminine body against me again, I almost melted. I had missed that soft touch. A lot.

"Sweetheart, you are a picture of perfection to me. I love your piercings. I'm just trying not to stare because I want you to be comfortable our first time," Anna said which warmed my heart. I put my arm around her and squeezed her to me which made her smile.

"I meant what I said just a moment ago. You are so beautiful and now after what you just said, more stunning to me than you can imagine," I said which caused her to tear up slightly. I think we both needed to hear we still had something to offer. "Now..."

I took her hand and led her to the bed, letting her crawl onto it while looking back at me. I started to feel a little anxious, but when I saw her ass curve and her wet slit peek out between her smooth thighs, my cock sprung to life. All my worries that I couldn't perform disappeared and I moved behind this wonderful woman.

"I am soaking wet, but I'm not sure how you're going to go... please be gentle, it's been a while since I've had a lovely thick cock," Anna said with a tone that was full of sensuality and desperation.

"Don't worry my dear, I have no intention of doing anything that doesn't pleasure you," I said putting my hand on her ass. She pushed back slightly and moaned.

I leaned over and kissed the small of her back, moving down to just above her fabulous rump when Anna put her hand on my head.

"Sorry," Anna said. "I, ah... not one for butt stuff, really. I liked what you did, but I'm not into anal... sorry."