Mystery Girl – Anal – StoryVa.com – Free Sex Story

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Mystery Girl

by Jake Rockwell

June 2022

I was leaving a meeting with my bosses in the upstairs corner office when my pocket began to buzz. My cell was set to vibrate, so the ringer wouldn’t disturb the meeting, and I hadn’t turned it on yet. The read-out said “Unknown Caller” so I let it go to messages. I figured if it was essential, whoever it was would leave a message.

I didn’t think much more about it until after I got home and jumped into my apartment building’s pool. As the cool, relaxing water washed the day’s stress away, my mind roamed to the call I hadn’t taken. When I got out of the pool, I strolled over to one of the chaise style pool chairs, took a sip of cold Modelo, picked up my trusty cell phone and hit the voice mail icon.

The caller was female and the message made me curious. “Hi, Jake,” she said. “You don’t know me but we have a mutual friend who gave me your number. I’m hoping we can get together.”

I almost turned the message off then because it sounded like someone trying to sell something, or get me to vote for some candidate I’ve never heard of. As I went to hit the off button, I heard something unusual for a spam call. “My name is Charlotte, and our friend Barb gave me your number,” she continued. “This is embarrassing for me, and I hope you don’t think I’m some kind of slut or something, but Barb and I were talking about Sex and your name came up. I’d like you to call me back, so I’ve attached a picture of me in a bikini to a text message, and sent it to this number. I thought you might want to see what I look like before you decide to call or not.”

The message ended and I opened up the text she said she was sending. There was this pretty brunette wearing sun-glasses and a skimpy black bikini. Her body was voluptuous, yet she looked like she could run a marathon at the drop of a hat. How could I know it’s the real girl on the call? I wondered about it for a minute or two and decided to make a Face Time call with her right now, so wherever she was, whatever she was doing, I’d see her face.

My call was answered after one ring. The smiling face I was looking at was the same one on the bikini girl attachment I’d just viewed.

“Charlotte?” I asked.

“Jake! I’m so glad you called. Smart to do a Face Time.”

“Actually, I’ve never had anything like this happen before, so I’m a little curious about what’s going on,” I said. “I wasn’t sure you were a real person.”

The girl laughed one of those sultry laughs that made me smile.

“Well, Jake, I know it’s you for sure. I’ve seen you out with Barb. She introduced us at Starbucks, but you probably don’t remember me,” she said.

“Now that I see your face, I do recall meeting you. You were wearing a red tank top and black shorts, if I recall.”

“Oh my god! You do remember me.”

“I try to remember pretty girls. Um…that wasn’t too chauvinistic was it? I only mean to say that you are very pretty. I could never forget a woman like you.”

“Jake, I wonder if we could get together sometime to talk. I want to ask for a big favor.”

“My pleasure, Charlotte. When are you Free?”

“I don’t actually have any plans for tonight, Jake.”

“Hey! That’s great! I was just planing to chill tonight, so spending time with you would be way better than hanging out alone at home,” I responded.

“Wonderful. Your place or mine?” Charlotte queried.

“Your choice. Wherever you feel comfortable works for me.”

“I’ll text you my address. Is seven o’clock okay?”

“Sure,” I said. “Do you like wine? I could bring a bottle if you like.”

“Got any white?” She asked.

“Chardonnay or Zin?

“Either works for me, Jake. I’m on my way home now. I’ll see you at seven.” Charlotte flashed a perfect smile and clicked off, leaving me a bit giddy and wondering what she planned for tonight that would go nicely with a bottle of white wine.

Mystery Girl

The Meeting

At seven o’clock I rang Charlotte’s video door bell. When the door swung open I was glad I came. She was wearing a pair of very tight, very short pink shorts, and a matching halter top that barely contained her plentiful pulchritude. Her waist was no more than twenty inches, and her hips curved out to what I guessed was thirty six inches or so. I guessed her height was about six feet, as we were eye to eye when I stepped into her foyer. No wonder I remembered her from only one casual meeting.

“Charlotte, it’s nice to meet you again. I Love your outfit. Pink is my favorite color,” I smiled.

“Barb told me you were a ‘pink-aholic’.” She laughed that amazing laugh and her blue eyes twinkled with obvious delight.

“Come on in and have a seat,” she said, leading me to the living room. I handed her the two chilled bottles of Finger Lakes white wines I’d brought.

“You said either Zinfandel or Chardonnay so I brought both,” I laughed.

“Perfect. Maybe we’ll drink them both.” Again, that sexy laugh.

Charlotte retrieved a pair of wine glasses and a marble wine chiller to keep the open bottle of Zin cool.

We talked about Barb, and I asked Charlotte what Barb was up to these days. The last I knew, she had met someone and fell hopelessly in Love. Charlotte said that was true, and in fact, they’d moved to Wyoming to live on his ranch. She said the happy couple were raising Quarter Horses and beef cattle. I was glad to hear that Barb was happy and doing what she wanted with her life.

After I opened the Chardonnay, Charlotte seemed a bit less inhibited and moved closer to me. Halfway through our next glass of wine, she had her head on my shoulder and her hand on my upper thigh. My arm was around her and my hand was brushing the exposed bottom of her left breast as we talked.

Charlotte took a big sip of her wine and tilted her head up with a look that said “kiss me.” I did, and the kiss lasted for minutes. By the time we broke for a breath the halter top was around her waist and I held her incredibly firm left breast in my hand. When I rolled her nipple between my thumb and first finger, Charlotte shuddered and sighed. By then, she was rubbing my hard cock through my shorts.

“Jake, I think it’s time to tell you why I called you,” Charlotte began. “Barb told me what a wonderful lover you are, and she mentioned that you enjoy my favorite sort of Sex.”

“Oh, and what would that be, lovely lady?”

She looked into my eyes for about thirty seconds without a word, then she sighed and said, “Anal.”

My cock jumped in my shorts, and Charlotte squeezed it tighter. “I confess, that I do Love making Love to a tight, Hot butt,” I said.

“Barb said you were gentle and considerate. I’ve been using a dildo that Barb picked out because she said is about the same size as your penis, and I think I’m ready to give the real thing a try.”

“I’ve had an erection since you answered the door. You are incredibly gorgeous and the sexiest woman I’ve ever shared wine with. If you’d like to give Anal Sex a try with me, I’m honored to attempt to please you any way you’d like.”

Mystery Girl

The Sex

“I was hoping you’d say that, Jake. I spent an hour preparing for Anal in case you agreed. I’ve cleaned up everything down there, and used a great tasting solution to make sure I’m not only clean, but yummy.” The laugh didn’t come, but a low moan escaped her luscious lips as she undid my shorts and my pecker popped out into the air. I told her it was freshly showered and ready, and she put her lips over my corona and ran her tongue around it as if to check.

“I’ve dreamed of this moment ever since Barb told me about you, Jake,” she murmured. “She was right. Your cock is the perfect size for my third opening.”

“I Love what you’re doing there. I’m not going anywhere, so you can do that as long as you like. She pulled my shorts off my legs and tossed them apart while I pulled my tee-shirt over my head.

Keeping my cock in her mouth and slowly taking it all the way to my balls, Charlotte rose up from the sofa and let me pull her skimpy shorts down her long legs. Now we were both naked and she was on her knees sucking my rock hard cock. Charlotte’s long brown hair fell down upon my thighs, and the erotic view of my cock slipping in and out of her inviting mouth was almost more than I could handle. She seemed to sense my state and gripped the base of my erection with her finger and thumb, quelling my natural urge to shoot a load into her throat.

“Barb told me you recover quickly after Cumming,” she said. “But I want to feel you to shoot the biggest load you can in my Ass.”

That almost sent me over the edge again, and again this gorgeous woman sensed it and tightened her grip on my cock. “Anxious to shoot, eh?” she whispered. “I Love sucking your cock, Jake. I’m glad you don’t have anywhere else to be tonight.”

While Charlotte made Love to my cock, I caressed her large, firm breasts with both hands. I squeezed them gently and alternated rolling her nipples between my thumb and finger. Each nipple roll, made Charlotte breath in deeply and sigh with pleasure.

As much as I was loving her ministrations to my cock, my mouth was watering in anticipation of eating her Pussy and licking her butt-hole. After many minutes of the mind bending Blowjob, I invited her to move into a sixty-nine position. I laid on my back, and she straddled my shoulders, while keeping my cock in her mouth and not missing a stroke. For being so tall and voluptuous, I couldn’t believe how athletic and flexible she was.

Her neatly trimmed Pussy smelled fresh and clean. I tasted her clit with a couple of little licks and felt her shudder. Then, I licked deeper and further along her deep purple slit, savoring her freshness and intoxicating aroma. Soon, my tongue found it’s way across her tiny pink anus. It tasted of strawberries, and I smiled at her thoughtful and thorough preparation. She said she was an Anal virgin, and I wasn’t gonna question it, but she must’ve studied hard to get ready.

When my tongue lingered a second at her puckered opening, Charlotte pushed herself back causing my tongue to enter ever so little. She emitted a loud moan around my cock which she simultaneously drove deep in her throat. That was a cause and effect that I truly enjoyed. I stuck my tongue deeper into her Ass and she again took my cock all the way into her throat. WOW! I could get addicted to this. I began stroking my tongue in and out of her butt, and she kept pace deep-throating my cock.

I moved back to her Pussy and started rubbing her Anal opening with my finger. Without missing a stroke, Charlotte handed me a plastic bottle labeled Anal Lube. I didn’t need to be told what she wanted, so I continued eating her Pussy as I unscrewed the cap and ran a generous amount of lube down her butt-crack and across her anus. The lube tasted of strawberries, too. I slowly and gently pushed first one then two fingers into her Ass. Her reaction was what I’d hoped it would be. She wiggled her Ass and pushed back, forcing my fingers all the way into her anus, an action that nearly made me cum right then.

I began sliding my fingers in and out of her tight little hole, introducing a third finger a little bit at a time. The third finger made Charlotte moan louder and push back harder. I noticed she was slowing the strokes of her mouth on my cock, taking in a little less of it each stroke. She soon took her face completely off my cock and raised her hips removing my fingers from her Ass. Then, she quickly spun around and gave me a long, deep kiss. When she broke the kiss she smiled sleepily at me and said, “I want your cock in my butt, Jake.”

Her Pussy was resting against my stiff cock, so all she had to do was tilt her hips forward and let my pecker discover the well lubed, completely relaxed object of my lust. As soon as my cock found the hole, Charlotte surprised me by dropping down and letting half of my length enter her Anal opening. It was tight, Hot, and as smooth as her soft lips. She smiled at me, kissed me lovingly and slid the rest of my cock into her butt. She waited for a few seconds, then began slowly and sensuously fucking my cock with her Ass.

I tried to think of something to distract myself, but her large, perfect breasts swaying inches before my face made thinking of anything but Charlotte and her fantastic body impossible. Now that I was finally fucking my first Ass that belonged to a girl who sought me out for Anal, I was ready to fuck her long and gently. From the look on Charlotte’s face and the movements of her body, I knew it would indeed be an all night fuck.

Charlotte purred, moaned, squeaked, and murmured “my god, Jake, I Love having a real cock in my Ass. Fuck me, Jake. Fuck my tight little Ass.” I was prepared to do exactly that, as long and as many times as she wanted. I knew I was hers for the taking, and she could do anything with me and my cock that she wanted. This has to be what Paradise feels like.

During the rest of the night Charlotte wanted to try every angle and position she’d researched while day-dreaming about her first Anal Sex. We did it in both cow-girl positions, doggie style, missionary, on her stomach. on her back with her ankles behind her head, and with her head on the floor while I stood up to fuck her Ass. Between position changes Charlotte would give my cock a few deep throat sucks and apply more lube to it.

I came in her Ass four or five times during the hours we fucked. The first time was about fifteen minutes into our first Anal insertion. From then on, she wanted me to cum whenever the excitement made it happen, but I trued to make each time last as long as she wanted. Her Pussy was left untouched.

When we finally fell asleep it must have been around five in the morning. The darkness outside her bedroom window was beginning to turn into light. Somewhere around noon I was awakened by a wet mouth sliding slowly up and down my hard cock. I excused myself for a couple of minutes to go relieve myself and wash my cock with soap and water. When I returned to the bedroom there was six feet of sexual goddess lying face down on the bed.

I picked up the bottle of baby oil Charlotte had laid out, and began massaging her back and firm butt. Charlotte moaned softly and told me how good it felt. Then, she reached down between us and took my cock in her hand. She smiled at me and said, “you must’ve shot a pint of cum in my butt last night, but I want to feel you Cumming in my mouth.” With that, she moved her head down to my cock and began the most amazing half-hour Blowjob I’ve ever had. She deep-throated me, licked around my corona, sucked my balls into her mouth, and finally hands Free face-fucked me to a climax that seemed to spurt for at least thirty seconds.

Finally, we got dressed and went out for lunch around two in the afternoon. We ate like we were starved, laughed at the silly man wearing a crown of kazoos outside the restaurant window, and vowed we’d get together again soon. Before I took her home and kissed her goodbye, we made a date for the next weekend. Charlotte seemed surprised that I asked her out again so soon. I just smiled and said, “I’d be a fool to not ask you out again. Not only are you a very gorgeous woman, you are the sexiest, most sensual, and enthusiastic lover I’ve ever known.

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