Past Transgressions

She reached down and began to stroke my manhood, which had only slightly wilted. As it regained fighting trim Liz swung a leg over me and using her hand to position me, impaling herself on my spear of love. As I slid inside she looked down on me and said, "Don't worry, you don't need a condom."

This was an obvious reference to our third lovemaking session in college. She had gone on the pill and told me that and said that I didn't need a condom. Hers was the first pussy I ever fucked bareback. It was so awesome that I pressured my fiancé (later my wife) into going on the pill.

As she ground her pussy down on me, she started talking, quietly at first, "Oh god it feels just as good as it did thirty years ago. Your cock was always the best. It fits my pussy perfectly. You always loved my titties. Do you not like them because they are smaller? I had them reduced about twenty years ago because they were killing my back. You can play with them. They won't break. They are just as sensitive as they were back then. Ohhhh, yessss."

The last was because I had reached up and cupped her tits and flicked my thumb across her nipples the way I remember she used to like. As I did that, I could feel her orgasm rip through her by the way her pussy muscles were pulsing on my cock.

When she came down from her climax high, Liz lay across me and began to kiss my cheek and neck. "You were the first guy to fuck me bareback, did you know?"

I shook my head and whispered back, "You were the first woman I ever fucked bareback. As well as the first one that swallowed after making me come with her mouth. You were my first titty fuck. You were also the first woman who told me what to do when I was eating her pussy and the first woman I fucked doggy style."

"I remember that time you fucked me from behind," Liz said brightly, "I thought you were going to fuck my ass. Were you?"

"I don't think so," I replied slowly. "I might have tried but you said, 'Not my ass' quite plainly so I wimped out and just slipped myself back into your pussy."

"Well," she said coyly, "Do you have some lube and we can fix that travesty of justice."

"In the top drawer of the nightstand," I said while vaguely pointing at it with my hand.

Liz rolled off me and rolled over to the side of the bed. I heard the drawer open and Liz's voice saying, "You have some anal cream here too. You naughty kids. So you guys had anal sex?"

"Sort of," I said slightly embarrassed. "We tried a couple of times. That tube is probably ten years old. I couldn't find a way to do it without hurting her."

"Let me give you some pointers," Liz said as she crawled back to me. "First, you take the anal cream and but a good glob on you." As she said this, I could feel her squeezing some of the cool gel onto my still hard cock. I started to feel my cock go numb almost immediately.

"Guys tend to get too excited and come too fast when they first start ass fucking," she said, "The anal cream numbs your dick and makes you last long enough for us to get past the pain and begin to enjoy the experience. The second part is to make sure you used enough on and just inside the lady's asshole. It will numb the initial penetration which causes the ass muscles to get stretched out."

Liz had turned with she returned so I had a good view to see Liz squeeze a generous amount onto her fingertips and reach back to spread it on her tiny butthole. After a few seconds of rubbing it in, she began to slide a finger in and out and then she brought her hand around to the front and squeezed some more anal cream and worked it in. This was followed by a good sized blob of the lube which was first squeezed onto my cock first and then more on Liz's fingers and transferred to her now slightly ajar backdoor.

"I think I'm ready for you now," Liz said in an incredibly sexy voice. I slid myself up onto my knees and positioned myself behind her. "Slow and gentle," she continued. "Just press your cock against my butthole. If it starts to hurt, I'll say, 'Stop,' please stop if you hear that."

"I will," I said as I placed my cockhead at the entrance to her backdoor. As I pressed slowly into her, she pressed back and I popped into her rectum without a lot of histrionics. Which was a first.

"You can keep going," she said. "Your cock feels so slick and smooth, like a silken dildo. That's it baby, slow and steady. Oh I feel your balls on my cunt." She snaked her hand around and found that I was balls deep into her. "Oh, yes, baby. You are all the way in. If I had known how to do it back then, I would have let you fuck my ass. You are a perfect gentlemen."

With that, I held still and she began to pull away from me and then push back on me. Oh my god the sensations were amazing. I had probably tried fucking my wife's ass less than five times in all the time we were married. The first time was an accident. We had already fucked once and she was a wet sloppy mess and when she climbed onto me, I pushed up at the wrong time and buried myself halfway up her ass. She shrieked and made me pull out. Three of the other times, I was so wound up that I shot my load just as soon as my cock entered her ass. The last time, I used the anal cream and I must have gotten some on my cock as I pushed into my wife because I lasted long enough to get a dozen partial strokes in before I blew my load. The downside is that when I came, I pushed all the way in and it hurt her, so I was banned from her backdoor forever.

Returning to the present, I grabbed Liz's hips and began to follow her rhythm.

"Oh yeah, baby. That's it. Go deep into my ass. I love it. I can feel your cockhead in my throat you are so far inside me. I knew you would be a good little ass fucker. Oh yeah baby, go faster. Pound my ass. Ohhhhhh. I've got two fingers up my cunt and I can feel your cock stretching my ass. Can we switch positions? I want to look at you while you fuck my ass."

With that, Liz pulled off my ass and lay on her back underneath me. She pulled me down and guided my cock to her back door. It wasn't working, so she rolled over and grabbed both pillows and stacking them up she lay on them under her hips. That brought her ass up off the bed and I was easily able to re-enter her forbidden hole.

The difference in friction was amazing and being able to see her face and watch the play of expressions as I fucked her ass was highly erotic. I was getting turned on and could feel the tightness of my balls signaling my impending orgasm. I think she could feel it or could see it on my face. Before I got to the point of no return, she looked at me and said, "Come on my tits, just like you used to do years ago. Wait until you are ready to pop then pull your beautiful cock out and bathe my tits in your sperm. Can you hold out for a minute more? Oh god I'm suddenly about to come. Oh goddddd. Oh goddd. Oh god. Ohhhhhhhhhh! Come on my tits baby. Bathe me in your warm cum. That's it. Oh you hit my mouth. Mmmm, your cum tastes so good. Oh it's so warm on my tits. It's so slippery and slimy. I love pulling my nipples when they have had a cum bath. Oh god, I'm coming again. Rub your cock on my clit, Yes. Like that. Slap it on my clit. Slap that bad nasty clit with your dick. Oh god yes. Oh hhhhhhhhh!"

As she slumped back onto the bed, I pulled the pillows from under her and then lay down beside her. She rolled over to me smearing my cum all over my chest from hers. I didn't care, I grabbed her and held her tight.

After a little while, she got a wicked little grin and said, "Are you too tired to come help a poor old lady wash your cum off my body?"

I roused myself from my almost asleep state to say, "I think I can manage it. As long as you can wash the cum you shared off my body."

She giggled and said, "Deal".

With that, we got up and headed hand in hand to the bathroom. We didn't fuck in the shower, but she did try to give me a handjob and I was able to make her come twice by soaping her groin while sucking her nipples.

After drying off, we fell into bed and were both asleep almost instantly. Tomorrow was going to be another day.

I woke with a start to an empty bed. Was last night just a wet dream and there was no Liz? No. It couldn't have been. Then I saw her suitcase against the wall and relieved, I knew it wasn't a dream. I grabbed a robe from the closet and went in search of Liz. It wasn't too hard to find her. I could hear her singing softly in the kitchen. There was a small stack of waffles next to her as well a pot of coffee just making that hissing spitting noise that signals the end of the brewing. She had her back to me and she looked to be wearing one of my shirts. It almost but didn't quite cover her ass. I snuck up on her and was able to wrap my arms around her and kiss her neck before she screamed.

She turned and slapped me on the shoulder. "You scared the shit out of me, you jerk. Oh my god. I am going to have to sit down. The last waffle is almost ready. Don't let it burn."

So I was left to watch the last waffle and pull it out when the waffle maker beeped. I put that one on a plate and slid it in front of Liz.

"You get the freshest one, since you did all the work," I said.

"Thank you sir," she said before she added some butter and a dab of syrup.

I poured two cups of coffee and we sat eating in silence until we were done.

"Those were really good waffles," I said. "What mix did you use?"

Liz giggled and said, "No mix silly. Those were scratch waffles."

"So what did you want to do today?" I asked. "You are my guest so your wish is my command."

"Well," Liz said slowly, "Other than fucking your brains out a few more times today. You said nobody can see into your pool area. Could we go skinny dipping? I've always wanted to go to a nude beach but I'm too chicken."

"We can do that," I said. "The plants screen the whole area except way down in the left side of the deep end. One of the fan palms died last year and I haven't replaced it yet. So there is a little area that Bob and Cleo's upper bedroom window can see about three feet of the pool and the some of the deck. As long as we stay out of that area, we are good."

"That is what I was hoping to hear," Liz said with a grin. "Let's take care of these dishes and go skinny dipping."

Ten minutes later, both of us in robes (I loaned Liz one of my spare robe) were on the back patio. I wrapped my arms around Liz as if to give her a hug and tugged on the sash and pulled the robe off of her. She squeaked and tried to cover herself. Then started laughing and how silly that was.

That was when I picked up my phone and started taking pictures of her standing naked on my patio. Her face clouded up for a second and I thought she would mad, but that passed and she started posing for me. She struck a pose and then put her hands under her tits and then bent over first showing her ass then grabbing both ass cheeks and pulling them wide to give an unparalleled view of her pussy and the little brown hole I had violated last night. It was slightly puffy and had a little tinge of pink, so I asked Liz if her butt was sore. She said it was a little, but it was totally worth it. She got a sly grin on her face and asked, "Did you want to go on that ride again big boy? Is that why you were asking?"

I laughed and said, "Of course I want to go on that ride again, but only if it doesn't hurt you."

Liz looked at me and said, "Let me tell you a secret. Anal sex always hurts. But if it is done right and it is done gently, the pleasure far outweighs the little bit of pain. What you did last night was perfect. I don't always come with a dick in my ass, but you got me off at least twice and both of them were huge climaxes. Pat yourself on the back. If you do what you did last night, any woman will be more than happy to let you fuck their ass as often as you want.

"Now since I'm running around naked, It's time for you to join the club." With that, she stepped forward and undid my sash and slid my robe off and threw it on a chair. After all the dirty talk and watching Liz pose naked for me, my cock was a little more than half mast.

"Is that all for me sailor?" she asked.

I nodded and she gently wrapped her hand around the shaft. Pulling lightly on me I could feel myself getting hard.

"Hmmmm. Seems a shame to waste a good hardon," she said. "Fortunately for you, my bucket list includes getting fucked in a pool or the ocean. I don't see an ocean, but I do see a pool."

I held out my hand and we walked over to the pool. I threw a raft in just before we got there. Liz gave me a look, but I refused to elaborate.

Once we had walked out into the warm water, I snagged the raft and picked Liz up and put her on it.

"Hey," she said. "What gives?"

I didn't say anything. I just spread her legs and applied my lips and tongue to her pussy.

"Ohhhh. I think I like this," she said. "I'm adding it to my bucket list so I can get it checked off. Getting head while floating in a pool. Oh baby. Oh. You just hit the spot. Keep licking there. Oh, yes. Put a finger or two inside me while you do that. Oh, yes baby. Oh you are hitting that spot inside me. Oh my god. Keep it up. Oh, I'm close baby. Not much longer. Ohhhhh. That finger in my butt. Ohhhhh here I go."

With that, she tried to lift her hips and it was all I could do to keep her from rolling off the raft. And then my face was splashed with this warm liquid that tasted funky but wasn't pee. And then Liz slumped and seemed to go limp. I pulled the raft into the shallow end and lightly touched her face. Her eyes opened but were not focused.

"Are you ok? Do I need to get the paramedics? How are you feeling?" I rapid fire rattled off questions.

"I'm ok," she said slowly. "I don't know what you did, but I went away to a beautiful place for a little while."

She looked at my face and ran a finger over my cheek, then tasted the liquid. "What is this?" she asked.

"I think you squirted," I said. "Right at your peak I saw this stuff gush out of you all over my face."

"Are you sure?" she asked, "I've never squirted before that I know of."

"I'm sure," I said. "It definitely came from you. I was right there in the line of fire."

"Can you help me off this raft?" she asked. "I think I need to sit down for a few minutes."

I picked her up and gently set her feet on the bottom. I helped her to the steps and she sat down.

Looking up at me, she had an impish grin on her face and said, "I had forgotten how good you are at eating pussy. And that finger up the ass trick really pushed me over the edge. Now, I know I said fucking in a pool was on my bucket list, but if you are up for it, I think I want to add ass fucking in a pool to that list."

"Well," I said slowly, "If you are serious, I guess I better go in and get some supplies. Pool water is not very good for fucking at the best of times. It dilutes your natural moisture and it can get pretty harsh. It is even worse I would imagine for trying to butt fuck since you need some real lubrication. I need to go find a bottle of silicon lube that won't wash off in the pool. If you are going to be ok, I'll be right back."

"I'll stay right here," she said. "Hurry back."

I made a dash for the house and hurried into the bedroom, totally ignoring the trail of water I was dripping everywhere.

I found the silicon lube in the "useless" toy box in the closet. That was where I consigned toys that did not get a positive reaction from my wife. As I turned to go, I spotted a jeweled butt plug and grabbed it just for grins.

As I returned to the pool, Liz had not moved from the step. She had slid over a little however and was sunning her tits.

"Found it," I said as I held up the bottle.

Liz took it and looked at the label. "Cherry flavored anal lube?" she said with an obvious question.

"Yeah," I said. "As you can see, it's almost full. It was used on one of my less than successful attempt to fuck her in the ass. The rest was used when we were in the pool or the hot tub. It is silicon based so it doesn't wash off in water. As you can see, that wasn't very often either."

"And what else did you bring me?" she said pointing at the butt plug.

"It's a little toy to help stretch your ass out. It's called a butt plug," I said holding it up.

"It's pretty," Liz said. "But it's pretty thick. Are you sure it will go in my ass?"

"Flip over," I said reaching for the lube.

Liz got on her hands and knees on the steps. Her ass was out of the water, so I shook the bottle of lube and opened the applicator tip and squirted a good sized blob between her ass cheeks. It was really thick so it stayed put until my finger dragged it down and I rubbed it around her little pucker.

When she started to moan little 'mmmms', I slipped the tip of my index finger in taking the lube with it. The 'mmmms' turned into 'ooohhhs' and she breathing deepened as my finger began sliding in and out, going deeper each time. I squirted some more lube and added another finger. As I was getting both fingers in past the first knuckle, Liz slipped a hand back and felt my fingers and got some lube on her index finger. She quickly brought it to her mouth and exclaimed, "Amazing, it does taste like cherry. Why would anyone make cherry flavored anal lube?"

I pulled my fingers out and brought my head down and stuck my tongue into her asshole. She shrieked and then relaxed as my tongue wiggled in her hole. "Oh that feels nice. I was not expecting your tongue," she said slowly.

I pulled my head back and reinserted my fingers. "Any other questions?" I asked.

"No, but my bucket list is getting longer. I would never have thought to add, shove a tongue up my ass to the list, but I can add it and check it off now," she said while grinning at me. "By the way, those fingers feel amazingly good. I was a little worried that my ass might be too sore after you fucked it so thoroughly last night, but it feels so smooth and slick, I am getting wet."

"Just hold on for a few minutes more and we will go get your fucking in a pool bucket list item checked off." I said as I picked up the butt plug. Squirting some lube on it I pressed it into her pucker and pushed.

"Whoa," she said, "Oh my goodness. That is not your cock, or your fingers. What are you doing? That feels weird. Not bad, but fuller than your cock. Oh, it is suddenly small, but I feel filled up."

I started to answer, but her hand came back to explore and it found the jeweled end of the butt plug.

"You put that thing in my ass," she accused.

"Yep," I said, "Now let's go fuck in the water."

With that I put an arm around her waist and pulled her into the pool. We both splashed around a little until I got my arm under her legs and carried her into deeper water. I stopped when the water was nipple deep on me. She was shrieking and splashing the whole time. Finally when I stopped and let her down onto her feet she stopped. The water was up to her neck.

"I am not sure I like this -" she started.

"You are fine," I said. "Making love in the water is easier in deep water. You float and it is like what I imagine making love in weightless space would be like. Jump up and wrap your legs around my waist."

She looked at me like I had lost my mind but she humored me. As soon as her legs were around me she felt better. That raised her head well above the water.

"Now what?" she asked.

"This," I said as I reached down and placed my cock into her pussy. Earlier I had greased up both her pussy hole and my cock with the lube so I was able to penetrate her completely in one smooth motion.

"Ohhhhh," she said. "That is nice. And for bonus points, I get to rub my tits on your chest."

"And I get to grab your ass," I replied.

As I began to stroke in and out of her, she moaned and arched her back. "Your cock feels like it is filling and stretching all of me and that butt plug feels like another cock is fucking my ass, but he is just waiting there. Oh god, this is incredible. You got me so horny on the steps that I feel like I am going to just explode again."