Caught Off Guard 5

For so long now, I've been frustrated. Due to our past, things we've said to each other during an argument or Lisa's inability to get over things she perceives from our past, our sex life has suffered. Not just our sex life but our overall intimacy.

Sitting at my desk, I often drift off thinking of what we should be, what we could be and what I want us to be. Today was no different, except today was. It's been a long time since I presented Lisa with 'The Game' (reference my other works) and it has gone totally ignored. As if I had never put it together, never came up with the list. Because it's been so long, I all but gave up on it.

Over the years, Lisa and I have had a decent amount of sex. When we first met, of course, we would fuck almost every time we were together. Lisa is 54 years old, I'm 53. She keeps in great shape, has a flat stomach, is 5'4" and about 125lbs. I believe her tits are 32C in size. They point to the ground a bit as she has had kids, but her nipples are glorious.

It's funny, I've been with my share of women and never really been a 'boob guy' and it's even more strange for me because I've always been attracted to very athletic women with tight asses, and I love a nice tight ass. Not the big asses like have been pushed on us from reality shows, but a really athletic, tight ass. I guess you could say I've always been an 'ass guy'. Anyway, with Lisa, I love her ass, but I REALLY love her tits. Don't ask me why, but I love it when she comes walking downstairs with no bra and I can see their shape under her shirt and they are swinging, rubbing on the material and making her nipples hard. Or when she would be riding me and I would look up and grab her tits and hold on to them as she would bounce hard on my cock, and squirt and cum all over me.

We've been together almost 9 years and, in that time, Lisa went through menopause, but when we first met, she would have her cycle. One day, at my apartment, it was 'that time', but we were starting to get hot and heavy. She had briefly sucked on my cock, (After nine years you'd think I would get regular blow jobs, but she has never really and truly SUCKED my cock. I've never cum in her mouth either. God, I want that!) and we were headed to the bedroom.

"I'm on my period. I know you don't like that." She said as a ping of let down swam through my body.

"Oh, ok. No worries." I said, hiding my disappointment.

"You can fuck my ass if you want." she quickly said.

Without a word, I bent her over the bed, pulled her shorts off and grabbed the lube out of the side table. I put some on my finger, and as I kissed and rubbed her ass, I slid my finger around her hole. Lisa looked back at me and said, "What are you doing?"

"Taking my time. I want you to really enjoy it."

"Oh..." She said as her voice trailed off, and immediately I saw her start to squirt, as juices ran down her leg, soaking my carpet. Clearly, she had been fucked in the ass before, but nobody had taken the time to think of her. Her enjoyment. Her pleasure.

That night, I fucked her ass twice. It was so tight, and I loved it, but she easily opened up to me and it was clear she had done it before. I'm 6' 3" and a big guy. My cock is commensurate to my size. Not massive, but bigger than most, and while the first few thrusts were a challenge, when she opened up, her ass swallowed my cock to the hilt. After that, we would have anal sex about every two or three months. I always wanted it more, but was, let's say, apprehensive to ask. For no other reason than I must not have been confident enough.

More recently, and over the years, I've loved giving Lisa back rubs. Inevitably it ends with a happy finish for both of us and we both end up sleeping great. But one time as I sat on her upper thighs and was really working her back, I leaned forward to add pressure and my cock pressed into her ass entrance. I didn't push it in, but I knew it was there and as I pushed my hands harder into Lisa's back, I could feel her arch her ass up, slightly and I perceived her 'wanting it'. As I worked my way down her back, I made sure to put enough lotion on my hands that I could also rub some on my cock. The next time I worked her upper back, I leaned forward again, and the head of my cock pressed up against her ass and started to push in.

A deep breath and, "Your cock is going in my ass." Lisa said.

I thought for a quick second and to my myself just said, 'go for it', so I replied, "You love it, and you know it."

Lisa said nothing, but moaned quietly and pushed her ass into my cock and it slid in almost effortlessly. I continued to rub her back but continued to thrust into her ass, deeper and deeper with every stroke and this is how most of our back rubs would go from then on. To this day, even with all our problems and us not having sex for months at a time, I still fully believe that Lisa loves anal. I think she is almost embarrassed to ask for it.

Yesterday, Lisa tried to ensure I knew her back was sore. She would bend over at the fridge, rub her lower back, let out a moan, and make sure that I saw.

"Maybe you should give me a back massage and..............." As she tailed off to a whisper that was inaudible.

"I'm sorry, babe, what was that?"

"Nothing."

And that's what happened. Nothing.

Today, sitting at my desk, my phone buzzed and made the familiar sound of chimes. My tone for a new text message. I looked down and saw it was from Lisa. I have a picture of her that pops up whenever she calls or sends a text. She looks beautiful in it and every time I see it my cock starts to get hard with anticipation and usually only to be disappointed. The message looked weird, so I picked up my phone, entered the code and pulled up the text message. It read: M005 1PM Bedroom

My heart skipped a beat and I found myself holding my breath as I realized it was a code from 'The Game' (Reference my story of that name) and my stomach did a flip. It had been so long since I put The Game together, that I had to look up the code. The 'M' Was for Massage, but what was 005? I looked up the code on my spreadsheet and it read, 'I massage you with lotion, full body, I finger you and lick you until you cum then slide myself into your ass, Until I cum.'

I couldn't believe this was happening. First off, Lisa had sent me a code from the game, but second was that it was for a massage with anal. I knew it! Waiting until 1pm was going to be hard.

The minutes seemed to take hours; the hours felt like forever but finally it was close. At 5 minutes to 1, I went to the bedroom, made sure I had lotion on the bedside table and that the bed was made with the sheets pulled back slightly. I heard Lisa coming up the stairs and as she entered the room, she quickly shut the door. Locking the dogs out of the room. She was super casual, today but wearing the sweats that I love that are old, cling to her ass and ride very low on her hips. She was wearing a loose-fitting t-shirt that she had pulled tight and tied a knot on one side so it wasn't so loose, and I could see her mid-section. Her tits were outlined nicely by the shirt, and she wasn't wearing a bra, I could see them moving under the shirt and her nipples were pressing into the fabric as they hung free.

Lisa walked over to the bedside and set her phone down and as she did, I put my hands on her hips and ran my hand around to her tight flat belly. My cock was already hard with the anticipation. I wanted this to be something that would happen again, so I took my time as I put my hands on her sweats and began to pull them down. Lisa didn't say a word, didn't turn around and didn't protest as the sweats fell easily to the floor. I stood up and ran my hands up her legs, to her hips and up her sides, raising her arms and pulling the shirt up over her head. I threw the shirt onto the floor, and put my arms around her, cupping her tits into my hands and feeling her hard nipples. I moved Lisa over to the bed and laid her flat on her stomach.

Standing by the bedside I quickly removed my clothes and then put a few pumps of lotion into my hand, rubbing them together to get the lotion warm. I began the massage on her upper thighs, working down her legs, making sure to hit every inch and gently massaging her feet. Then back up her legs, upper thighs and let my fingers graze her pussy lips and clit as I worked my hands up to her ass and massaged her cheeks deeply.

"Roll over."

"But, you didn't do my back.."

"I will, but want to give you an all over massage, so I'll do your front first."

Lisa quickly rolled over and I started the same process. Working her thighs, down her legs to her feet, then back up. I started working her inner thighs and Lisa spread her legs which parted her pussy lips, just slightly. I could see she was dripping, and I ran my thumb and parted her lips. I could hear Lisa breathing deep and I pushed my thumb into her pussy, then out and switch to two fingers. I slowly fingered her pussy and massaged her inner walls and G spot. She came quickly, squirting her juices over my fingers and hand, soaking the sheets. With that, I removed my fingers, put more lotion in my hands and began working her hips, abs, and up to her tits, massaging them with love, passion and lust. I worked my way over her arms, hands, and fingers and then back over her breast, abs, hips and pussy, sliding my fingers in again, as deep as possible. Then out and down her thighs to her feet.

"Roll over." And Lisa rolled over without question.

This time, I mounted the bed, sat just below her ass, and straddled her thighs. More lotion on my hands, rubbed some on my rock-hard cock and began working her lower back. As I moved up her back, I rocked my hips forward for leverage and each time, the head of my cock would lightly press on Lisas waiting ass hole, and each time, Lisa would breathe a deep breath of anticipation. As I got up to her upper back and shoulders, I made sure that my cock pressed harder on her hole, but not hard enough to penetrate. Lisa tried to press her ass against me, wanting my cock, but I would rotate slightly away so it wouldn't go in. I wanted to finish the massage.

After working her upper back, I moved lower, put a little more lotion on my cock and in my hands, then went back to her upper back. As I started to press hard, I rolled my hips forward and my cock pressed hard against Lisas hole, she pushed into it and the head of my member slipped into her ass.

"Ohhhhh, fuck yes." She said as she exhaled a deep breath.

I pushed my cock further in, then pulled back so the head of my cock would spread her tight entrance again and Lisa whimpered. Then I pressed down hard on her back and hard with my hips, sliding my 7-inch cock deep inter her ass. Lisa let out a loud moan and arched her ass into me, trying to get every inch of me into her. I rocked forward then back slowly then forward until my cock was almost as deep as it could go. I was still straddling her thighs and slowly pumping in and out.

I pull back one last time and let my cock slip completely out of her and Lisa let out a long sigh and moan. It was clear she wanted more, so I grabbed her by the hips, pulled her to her knees and she kept her face on the bed, turned sideways and she spread her legs slightly, giving me the invitation. I moved between her legs, as close as I could, and pressed my cock into her ass. As I did, Lisa pushed back hard against my cock, taking it fully. She began moving forward and back, slapping her ass against my pelvis, and ensuring my cocks was ramming in her ball's deeps with each thrust. She loved it and wanted more.

"Fuck me, Fuck my ass. I want you to fuck my ass hard!" As she was backing into me. With that, I grabbed her hips and started to ram my cock in as hard and as fast as I could. With every thrust, her face was being pushed into the bed and with every thrust she would grunt.

"Fuck my assss! Harder! Harder! I'm going to cum!" And with that, Lisa began squirting all over my thighs, soaking the bed. I had never seen her squirt so much, even when she would ride me and would be splashing down onto my cock, hard. I continued to fuck her ass, but at this pace and with her cumming, I couldn't hold back and with one final thrust, as hard as I possibly could, my cock exploded deep in her ass, filling her with cum. I pumped about 10 more times, each time with more cum pumping into her until my cock started to soften and it slipped out of her now gaping ass. Lisa's ass was open, flexing and twitching as my cum started to pump out of it, down her crack and to her pussy lips, blending our fluids and dripping onto the bed.

I collapsed on top of Lisa, both of us laying in a puddle of our love juices. As I rolled off her, she sat up on the edge of the bed, stood up and had to steady herself, her legs and ass weak from the pounding.

"We can reuse codes, right? Can we do multiples?" she asked as she walked into the bathroom. I didn't answer but couldn't wait for the next Code to be texted to my phone.

Sitting at my desk, my phone buzzed, and I heard familiar chimes of the ring tone. Sometimes I hate my imagination, how I slip into my daydreams. They are so vivid and real, but when I come out of them, I am always in a better mood. Even if it wasn't real. I'm always hopeful that our relationship will become what it once was and more. So much more. I glanced down at the phone. It was Lisa's picture, and I checked the message.

B001 5pm Car

I checked the sheet: We drive to the ridge, bringing a couple of cocktails with us and Lisa gives me a blowjob and swallows my cum as we hang out and watch the sunset.

I can't wait for 5pm.