Dinner was fantastic; there was a posh resort near the town where we were staying that served up some delicious seafood dishes. After dinner we retired to my hotel where we started talking about our lives some more.

“So, a vanilla sex life huh?” April asked.

“Yeah, pretty much,” I replied. “Nothing fancy at all.”

“Well, you sure picked up on what I like pretty quickly!” she laughed.

“I’m curious,” I said, “and you don’t have to answer if you don’t want to, just how… extensive is your experience with other people?” I asked.

“You sure you want to know?” I nodded. “Okay then here goes. Fasten your seatbelt, this might be a bumpy ride!”

She began by explaining how she’d lost her virginity the summer she turned sixteen to a summer camp counselor. A number of boys throughout high school had enjoyed her favors but it wasn’t till she got to university that her sex life really took off.

“It might be easier to tell you what I haven’t tried,” she said. “I’ve had relationships with both men and women; I don’t prefer one or over the other, each has their benefits and drawbacks. I’m not into the whole bondage scene, nor am I into watersports or pain.”

“So, you’re bisexual then?”

“I like to think of it as ‘try-sexual’, there’s not much I haven’t tried,” she replied, laughing.

“Aren’t you concerned about catching something?” I asked.

“Well, I have caught a few things, nothing that isn’t curable thank goodness. Lately though I’m a little less carefree about who I sleep with,” she said. “I know, it doesn’t seem like that with you. I hope you don’t mind but I checked you out before I agreed to go out with you.”

“Really?” I asked. “I assume you liked what you found out?”

“Oh yeah! I definitely liked what I found out! I wouldn’t have gone out with you otherwise!” she exclaimed. We both laughed at that and then settled back down.

“I’m glad,” I answered, leaning in to kiss her. “I really like you, and not just in bed. You’re funny, saucy, sweet and a little bit devious. I never quite know what to expect with you.”

“I like you too Stuart, a lot. It’s good to keep people guessing sometimes. Hang in there, we’ll see where this goes.” She shifted onto the bed and patted the mattress beside her. “Come sit here,” she said, “and we’ll figure out what might happen down the road, at least for the next few days.”

I was intrigued as I moved to sit beside her. We kissed again, more urgently this time until she pushed me away.

“So,” she whispered. “I’m going to ask you some rather personal questions about your sex life, about your desires and fantasies. If you’re uncomfortable, you don’t have to answer but, if you trust me, I think you’ll like where this goes.” I nodded my head, unable to speak. This woman was quite unlike anyone I had ever met.

“Okay. You don’t have to say anything, just nod or shake your head.” I gave her a thumbs up. “You’ve never had sex with a man?” I shook my head no. “Ever want to?” Again, no. “Alright we’ll cross that one off the list.

“Ever had a threesome? Foursome? Moresome?” Again, no. “Would you like to?” I waggled my hand with a maybe gesture. “You should really try it, it’s awesome! The thing is you can’t get hung up on it. It’s just sex without attachment. You enjoy it for the erotic physical act that it is. Some people have a tough time having a threesome with their significant other, can’t separate the sex from intimacy. We’ll see about that one.

“Ever watched two women have sex?” Another no. “Would you like to?” Two thumbs up and a big grin was my reply. April laughed and fell back on the bed. “Men! You are all so easy to read! We’ll definitely put that one on the list!

“Ever tried anal?” I shook my head. “Want to?” I finally spoke.

“Was never with anyone who even mentioned it to be honest. Good old-fashioned sex was always enough for me,” I said.

“Well then,” she cooed. “You are in for a treat!” She got off the bed and went to retrieve a small vial from her purse. “Lube, it’s the answer to almost any problem!” She set the vial on the nightstand. Starting with unbuttoning my shirt, she slowly undressed me, making her way to my belt. As she lowered my slacks, she took my cock out of my boxers and let out a long, “mmmmmmm…”

She took me into her mouth, slowly using her lips and tongue to give me the most exquisite sensations. After a bit she stepped back and said, “Now, you get to undress me!” Carefully, I removed her blouse, her bra, pulled down her slacks and finally her panties, kissing her all over as I did so. “For a vanilla guy, you sure do know what you’re doing,” she breathed, writhing as I found her ticklish spots. Taking her by the waist, I lifted her up onto the bed, moving between her legs so I could savor her sweetness as I had done earlier in the day. After a few moments I felt her shift as she reached for the small vial on the night stand. Handing it to me she said, “Put a little on your finger and slip it right in my bum.”

I did as she directed and was rewarded with a sigh as my index finger slipped inside her backside right to the hilt. I was a little surprised at the lack of resistance to my entering her. Keeping my finger in her ass, I slipped my thumb inside her warm wet pussy to lubricate it before starting to work on her clit. Her hips would twitch every time I flicked it so I knew I was doing something right. A minute or so later, she pulled herself off me and took the vial of lube off the covers where I had dropped it. She applied a little to my cock and then to her little rosebud opening. She flipped onto her stomach and said, “It’s time. Don’t worry, it might seem like you’re hurting me at first but I’ll enjoy it as much as you do.”

I positioned myself behind her and placed the end of my glans up against her little hole. Having never done this before I wasn’t sure how hard to push so I started gently. Her ass resisted opening so I pushed a little harder but still no entry was granted. It was then that she pushed back against me and my head slipped inside her. She let out a little squeak and panted, “It’s OK, don’t stop now! Just go slow.” Again, I did as she instructed as I watched my seven inches disappear inside her asshole. My hands were on her hips so she reached for my right hand and moved it underneath her body, positioning my fingers onto her pussy.

“OK, you can go now, play with my pussy while you fuck my ass!” she growled, pushing back against my hips. I slid a couple fingers inside her as I started moving my dick out and in, slowly at first but gaining speed as we found a rhythm. She fell forward and buried her head in the pillows as her fingers joined mine, playing with her clit as I fingered her pussy. Her ass was so tight, tighter than anything I had ever felt before. The sensation was just raw, animal lust as I fucked her. I could feel my fingers against my own cock as it thrust into her backside. It was well that I’d already come a couple times that day else I wouldn’t be able to hold off bursting inside her.

April started moaning louder as I fucked her; her moans turning to squeals and then to screams as we both neared our orgasms. I tried to hold back until she came but it was no use, my orgasm peaked and I emptied myself inside her. Holding myself against her bum, she gave her clit a couple last flicks and she released herself just as my own excitement began to fade. Powerfully, her anus clenched against me, her pussy spasmed onto my fingers as she came. Thankfully she did not flood the covers as she had done earlier in the day, otherwise we’d have had no place to sleep. She moved her hips back and forth a few times to slide me out and back in before collapsing onto her stomach, my cock slipping from inside her, both of us completely out of breath. I was spellbound by the sight, her pussy swollen and red and a little rivulet of my come leaking from her ass.

I rolled off her, lying beside her and enveloping her in my arms. “So, you like that?” she asked quietly.

“Wow, never in a thousand years would I have thought that would feel so incredible!” I answered, hugging her as tightly as I could.

“You see, I told you it would be fun!” she giggled. “So will all the other things you’d like to try, if you’re willing.”

“I look forward to it,” I answered. She extracted herself from my arms and went to the washroom, coming out a few minutes later completely naked. She pulled back the covers and climbed into the bed as I got up to clean myself up. When I came back to bed I had on my boxers.

“I usually wear a nightie to be but I prefer to sleep naked when I’m with a lover, especially the first time we sleep together.” Taking her cue, I slipped off my underwear and crawled in beside her. We snuggled and kissed, becoming used to the feel of the other’s nakedness next to our own. Presently we drifted off to sleep.

When I awoke, April was still sleeping. She had tossed the covers off herself through the night so I gazed in wonder at her body. Being in her fifties, she didn’t have the perfection of a younger woman but she was unquestioningly beautiful. Her tummy was taught and her beasts had only a little sag, they were still full and round. I could see why she was proud of them. Getting out of bed, I pulled the covers over her before I went to the washroom to complete my morning routine. After I finished in the washroom, I started making coffee. As the coffee maker made its noises, she stirred, rolling over and opening her eyes.

“Morning handsome,” she said groggily.

“Good morning, beautiful lady, did you sleep well?” I asked.

“Like a woman who was well and truly satisfied,” she answered.

“I’ll bet you say that to all the boys,” I said lasciviously, moving over to the bed to kiss her. She must have gotten up through the night because there was no hint of morning breath. “So, what would you like to do today?”

“If it’s all the same to you, I’d like to lay off sex today. It’s been a while and I’m a little tender this morning. I’m famished, how about we find a café and get some breakfast?” she said, climbing out of bed. I stared at the full rounded bottom I’d fucked only a few hours before as she sashayed into the washroom. I heard the shower run for a few minutes, after which she came out dressed. I was sitting in a chair beside the desk in the room; she came over and sat in my lap, wrapping her arms around my neck and kissing me softly, as a lover. “Anyone ever tell you you’re pretty good I bed?” she asked. I shook my head. “Well, you are. And I should know, I’ve had a few lovers in my time!”

“Is that what I am to you?” I asked, “Just a lover?”

“For now,” she winked at me, “we’ll see where this goes.” She got off my lap and pushed me towards the washroom. “Go on, get dressed, I’m starving!” I got up and went to the washroom, gathering fresh clothes on the way. When I emerged from the washroom, she was looking at some information on the local area. “There’s a community market today down by the marina, how about we give that a look. I’ll bet there’s all sorts of interesting things to see and find there.”

“Sounds perfect,” I answered. She was wearing the same outfit she had worn the night before so she gathered up her clothes that were strewn about the room and stuffed them into the large handbag that she had brought. “We can swing by your hotel so you can get fresh clothes before we go, if you like.”

“Sure, that’s sounds good,” she replied as we headed out the door. My room was accessible from the outside and as we went out, I noticed another couple a dozen or so feet away. We exchanged good morning pleasantries and then the lady of the couple leaned in toward her partner and whispered something I couldn’t hear. I said nothing as we walked to my car. I opened the car door for April and as I walked back around the front to get in the driver’s side, I glanced back over towards them. The gentleman gave me a discreet thumbs up and the lady a little golf clap. It was obvious that they’d heard us the night before as I was fucking April’s bum. I was laughing as I got into the car.

“What?” she asked.

I just pointed at the couple and said, “I think we might have been a little too loud last night. She’s giving us a private standing ovation.”

April looked at them and noticed their reaction. She just swept her hair into place and smiled. “Perhaps,” she said, “but I wouldn’t change a thing.”

“Me neither,” I said, “not a thing.”