No Regrets Bowl Pt 01

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I'd met Carly on an internet dating site, which is not unusual these days. The one we used was geared towards 'mature' singles, which we both were. We messaged a few times then exchanged phone numbers and within ten days we met for our first date. I managed not to screw it up and so we had several more dates, each one ending in a kiss hotter than the one before.

On date five I dropped my hand behind her as we kissed and massaged her lovely ass cheek. She moaned into my mouth which I took as permission, so I moved my other hand behind her and caressed both ass cheeks. More moans.

She pressed her breasts into my chest and I thought I felt hard nipples. That caused a hardness of my own and, as we were standing tight together, she couldn't miss it. Pushing her hips further into my groin she began moving up and down, stroking my cock through our clothes.

"Let's go to my place," Carly said, "it's closer than yours."

"Love to," I replied as we separated and went to our respective cars. I followed her as this would be my first visit to her place. When we arrived it was a neat, attractive little ranch well-suited to the suburban area in which she lived.

"Very nice," I said as she unlocked the door and led us in. It was obvious a single woman lived here, but unlike many she hadn't gone over the top with the frilly, feminine stuff. The soft pastel walls and bolder color upholstery would have worked fine for a single male with just a change of the pictures on the walls and knick-knacks scattered around.

"Thank you, but I didn't ask you here to critique my design efforts," she said as she closed the gap between us and grabbed my cock through my jeans. "Awwww, someone went to sleep on the drive." She was correct, I'd lost my erection while we drove but I knew that would be rectified quickly.

Taking my hand, she led me into her bedroom where I noticed the bedspread and sheet had already been turned down. "Do you always turn down the bed or were you planning for something else?" I asked.

"Hoping rather than planning. Are you objecting?" she said.

"Not at all," I replied as I unzipped her sundress and slid it over her shoulders and down to the floor. That started a bit of a war as each of us tried to undress the other at the same time. I won when I dropped to my knees and pulled down her panties, leaving her naked and my face next to her pussy. Naturally I leaned in for a kiss and a lick, causing her to shudder with pleasure.

She grabbed my arms and pulled me up to standing then knelt herself to remove my boxers and socks. We were both fully naked now and climbed into the bed. We kissed as we explored each other's naked bodies with our hands. Her C-cup breasts were full and heavy and her nipples prominent. Her pussy was already wet and she moaned loudly when I touched her there.

"Wait!" she cried and I left my hand where it was but stopped moving my fingers. She slid further down the bed and laid her head on my abdomen, just above my cock head. She opened her mouth and took my head into it, never touching me with her hand.

Up til now we hadn't spoken much about sex. To be honest, I was concerned her tastes might be too conservative for me. Not that I'm some kink-master, but I like variety. I've had threesomes, anal, bondage games and so on. Spending the rest of my admittedly senior life having nothing but missionary with the lights out wasn't in my plan.

If this was any indication, I had nothing to worry about. She gobbled my cock like she hadn't eaten in days, licking, sucking, and stroking for all she was worth.

"Hon, you're going to make me cum if you keep that up," I cautioned her.

Taking my cock out of her mouth she asked, "Can you stay the night?" When I answered affirmatively she went right back to what she was doing and, as I had said, got me very close.

"I'm going to cum," I warned her. 'Mmmmm mmmmm' was her mumbled response. Hearing that I relaxed and let her bring me over the edge, shooting several spurts of hot cum into her mouth. When I did she stopped stroking so she wouldn't over-stimulate my very sensitive head, but held me in her mouth until I started to soften.

When she released my cock she climbed back up next to me, opened her mouth to show me my cum, then closed and swallowed before opening again to prove she had.

"That was great, hon. It will take me a while to recover so let me return the favor. Do you prefer I get between your legs or would you like to sit on my face?" I said.

"Oooooo, face please. That fits right in with something I want to discuss with you soon," she told me as she straddled my head and lowered her dripping pussy to my mouth. I immediately began licking her slit and driving my tongue into her opening. I kept that up for several minutes then moved up and took her clit between my lips, sucking and occasionally nibbling lightly with my teeth.

My hands cupped her ass cheeks and I let my fingertips wander into her butt crack. I didn't go far, avoiding her back door as I had no idea how adventurous she might be. I didn't want this to be our last romp in bed.

My attention to her clit was having the desired effect and in a couple more minutes she screamed "Yessssss!!!" and came, her entire body shaking and her pussy throbbing. She ground it into my face until it actually hurt but I didn't resist or stop her. I let her ride my face until her orgasm ended and she fell off me to the side.

"That was fucking fantastic, and I hardly ever swear! You need to give me the name and number of the woman who taught you how to do that, cause I owe her big time!" she exclaimed. Then she reached out and took my cock in her hand. It was already a semi and with a little attention from her I was soon fully erect.

This time we did settle for missionary, both a bit tired from the intensity of our first orgasms. Or in her case, first three. Her pussy felt marvelous on my cock and the moans she was making suggested she liked how my cock felt in her. We both pumped our hips in synch until she said "Babe, I'm getting close again."

"I am too so go for it hon." She did and as soon as her pussy started clenching my cock I shot off again. Once we stopped I remained on top of and inside her until I softened, shrank, and slipped out of her. I rolled over to take my weight off her and we laid side by side, slightly sweaty and breathing hard. Once we caught our breath we kissed and fell asleep in each other's arms.

I woke the next morning to the feeling of my cock being fondled. I was still soft but knew it wouldn't stay that way long, so I said, "Be right back," as I went into the en suite to relieve myself.

"FYI, as far as I'm concerned you don't need to shut the door if you're only peeing. Pooping should be private but pee is no big deal," she called out.

"Great, I feel the same way. Saves wear and tear on the hinges too," I grinned. She smacked my arm playfully then resumed her fondling but with full intent now. It didn't take long for mini me to be standing at attention, throbbing as if to say 'Ready for duty, ma'am!'.

I waited to see how she would proceed and in a few seconds she sat up, threw her leg over mine and straddled my hips. She rubbed her slit up and down my shaft, lubing it with her wetness. Satisfied, she lifted herself up, reached between her thighs, grabbed my cock and pointed it to her opening. Then she lowered herself down on me completely.

When she had me fully inside her she stayed still, on the exterior at least. Her pussy started squeezing my cock rhythmically. She was squeezing so tightly that I concluded Kegels must be part of her regular exercise routine.

I moaned at the sensations and she smiled slyly. Then she started stroking herself up and down my shaft, pulling all but my head out on the upstrokes and pressing our groins together tightly each time she sank down.

Carly leaned down to kiss me and I grabbed her nipple, squeezing it and making her moan. I raised my head and took the other one between my lips, suckling and licking. All this was getting to Carly and her stroking on my cock started going faster and faster. I felt my cum start to well up in my balls, a pressure I don't know how to explain to anyone who hasn't felt it.

"Babe, I'm getting close," I told her.

"Go for it. I want to feel you cum inside me again," she responded.

I started to cum and raised my hips, trying to drive my cock deeper inside her than possible. That had the effect of pushing her to the finish line. Once again her orgasm was actually a whole series of them. I thought I counted four but could easily have missed one or two. She mashed her clit into my pubic bone and ground it back and forth until she finally reached the end and collapsed onto my chest.

The next two weeks were more of the same. We got together nearly every night, sometimes at her place, others at mine. Since we were both retired we had few other commitments. Carly moved her gym membership to the location I use and so we spent every Sunday, Monday, Tuesday, and Thursday nights at my place since it was closer to the gym we used three days a week. Tuesday night was because I volunteer building houses every Wednesday. Wednesday, Friday, and Saturday usually found us at her place, taking advantage of the many options being close to the city provided.

That Friday two weeks out found us driving to her place after we finished working out. We stopped for lunch and then did some window shopping during the afternoon. Carly kept trying to upgrade my mostly jeans and t-shirt wardrobe and I wanted to make her happy so I let her drag me to the men's clothing store.

With the hatch of my Mini loaded down with bags full of clothes, we discussed dinner plans and decided we'd go to her place and order either Chinese or pizza. "I have something I want to discuss with you. I mentioned it the first time we had sex but you may have forgotten," she said.

"No, I remember. I figured you'd bring it up when you were ready. I don't like nags so I don't nag."

When the Chinese was delivered we sat on her sofa, so we could dine on the coffee table. As I helped myself to an egg roll, some wonton/egg drop soup, and Moo Goo Gai Pan with rice, Carly opened the end table drawer and took out a piece of paper. Placing it face down on the sofa, she served up her dinner and we started eating.

Between bites, Carly started the discussion. "I imagine you've heard it said that, at the end of life people don't regret the things they did but rather those they didn't do. I don't completely agree with that, but neither do I want to lie dying and think about all the things I wish I had done."

"That makes sense, and I agree with you. So what do you want to do - travel, learn a language, adopt a pachyderm?" I asked only half joking.

"Nope. My things are sexual," she said, then paused to gauge my reaction.

"Okay, you're going to have to explain that much more," I told her.

"It's a little hard for me to admit this, but I really like and trust you. So far I've had a very vanilla sex life. Believe it or not, the only positions I've ever had are the two you and I did that first weekend - missionary and cowgirl. Yes, I've given blowjobs and had guys go down on me, but until you offered I'd never sat on anyone's face. No doggy, deep throat, anal, bondage. None of the things more adventurous people do."

"That's okay, hon. Everyone's sexual experiences are different. Nothing to be ashamed of," I reassured her.

"Oh, I'm not ashamed, I just don't want to have any regrets. The idea of anal, for example, scares me somewhat but what if I try it and love it? Same goes for lots of other stuff. So I'm asking if you're willing to help me experiment," she said, pleadingly.

"Of course I will. I have to tell you I have what is apparently significantly more experience than you do. But there are still things some people like that I won't engage in. If you want those things we'll have to figure something else out," I told her.

"Well, look at this list," she said, turning the paper over and handing it to me. "These are the things I know I want to try. There may be more once we go through these but that remains to be seen."

I took the paper and scanned the list:

Positions

Spanking

Paddling

Watersports

Anal

FMF

FMF - other sits on my face after you fuck and cum in her

DP - 2nd F with strap on; you in my ass

Spit roast - 2nd F with strap on, you in my mouth

Facial

Facial then restaurant

Tied to bed, basic sex

Talk dirty

Handcuffed blowjob

Deep throat

BDSM

"That's quite a list, hon," I said.

"Is there anything on it you won't do?" she asked.

"Not per se, but within a couple are variations I won't do. I once dated a woman who was seriously into the whole Master/Sub aspects of BDSM. She wanted a Master/Slave contract and loved pain. She wanted paddled and whipped hard enough to leave scars, and that's just not me. I'll spank or paddle you until your ass is good and red and you may still be sensitive sitting down the next day if that's what you want, but that's as far as I go," I explained.

"Oh, that's fine. I don't want any scars, I just want to push my boundaries to see where my limits are," she told me.

"Okay. Are these in any particular order? How are we going to go about them?" I asked.

"First, you have the right to remove anything you refuse to do, right now. Once we have a completed starter list, I thought I'd cut them up and put them all in a bowl. Each time we want to experiment we'll pull one out. At that time, you can also say I don't want to do that today. Then we'll put it back and draw another, okay? But since it's my list I can't refuse once its pulled."

"That sounds like a plan. You've really thought about this, haven't you?"

"Yes, starting even before you and I met. I was really hoping to find someone I could possibly spend the rest of my life with. And hoped he would be good with this idea. You fit the bill on both counts," she smiled.

"And how often do you want us to pull a slip out and try something?" I said.

"I don't know. I think we should play it by ear. When I'm in the mood I'll ask if you want to and we can go from there."

"Okay. A few more things. You have several threesome activities. Wouldn't spit roast and DP be easier with another man rather than a woman with a strap on?" I inquired.

"Probably but I don't want to be with any other man. I want to be with a woman because I've often fantasized about it. So why not use her for the other things we need a third for," she explained.

"Makes sense I suppose. Do you have a woman in mind?"

"Actually I do, sort of. You've met her - my friend Lauren we ran into at the pub last week. She's bi and has dropped a few hints that she'd like to be with me, so I figured I'd ask her if she would be okay with a threeway with you involved. What do you think?"

"I hardly know her but physically she's very attractive. And I got sexy vibes from her. Learning she's bi makes perfect sense - she gives off the aura of a person who really likes sex," I said.

"It's settled then, I'll ask her. If she says yes we might bend the rules and intentionally pull a threeway slip out of the bowl and arrange the date."

"Do you have handcuffs and stuff to tie you down," I asked her.

"Not yet. I thought we could go online and order some of that stuff tomorrow."

"Okay. One more thought. Another woman I dated years ago liked me to tell her what to do. Not wanted to blow it, I asked if there was anything off the table. She thought for a minute and said 'don't pee on me first thing in the morning.' I should have asked why but I didn't. My guess is that pee is strongest first thing as you haven't been hydrating during sleep. You might want to think about that before we try watersports."

"Good idea. Might be best to try that later in the day, at least the first time. Also, once we try something we will move that slip into a second bowl, to use when we finish the original one. If we try something and either of us doesn't want to do it again, we toss the slip instead of putting it in the second bowl. And after we finish bowl one and start on two, I get to say 'not today' just like you can starting now."

"That's fair. What if there are things I'd like to add to the list?"

"Like what?"

"One I already know I'd like to experience is a prostate massage. A woman once tried it but couldn't find my prostate. And I've sometimes fantasized about being pegged. I honestly don't know if I would ever go through with it, but who knows? Maybe one day I will."

"Wow! Interesting. I would say that if you want to add things to the bowl I get veto power over them and the 'yes, but not tonight' option."

Having asked and answered all the questions we had we cleared the dinner things we went to bed. We got into missionary but after entering her I slid my arms under her thighs and lifted her legs until her knees were on my shoulders. "Oh!," she cried, "That's new."

I fucked her like that for a bit then lifted her hips off the bed and continued pounding her, my cock at a different angle so it hit her G-spot. I did that for a few strokes then set her back down so my shaft could rub her clit as I stroked.

Alternating between her G-spot and clit did exactly what I knew it would. In just a little while she was screaming out as her normal, multiple rolling orgasms coursed through her body. I stopped when she cried "Yes!" and let her settle down. When she recovered I pulled out, flipped her over, and took her from the back, reverse missionary. I only lasted a couple of minutes before slamming my cock deep into her and spraying her cervix and pussy with my cum.

When I calmed down I pulled out of her and laid behind her, pulling her into the spooning position. I reached under her arm and took her breast in my hand as we fell asleep together.