Annie, Jenny, and Me
Copyright© 2022 by Master Jonathan
Chapter 4
Romantic Sex Story: Chapter 4 - This story is about a guy new to the apartment building who befriends and ends up having sex with a divorced woman across the hall. When her daughter comes to town, she introduces him and he has sex with her as well. Although there are three characters in this story, two of whom are mother and daughter, there is NO incest – he has sex with each one individually. So all those who dislike the idea of incest can read this story without worry.
Caution: This Romantic Sex Story contains strong sexual content, including Mult Consensual Heterosexual Fiction Sharing Anal Sex Analingus Masturbation Oral Sex
“Yeah, the poor girl is really feeling it this morning! What did you do to her, anyway?” she said.
“I just showed her how the big girls play!” I said. “That’s what she wanted. She begged me to fuck her like I fucked you! Of course, I didn’t, but I came close enough apparently!”
“I’ll say. And tonight you get to play with ‘the big girl’ – unless you are too tired!”
“You just be ready to fuck, baby!” I said.
“Mmm, I’m always ready to fuck. I just love the feeling of that big fat cock ... in whichever hole you choose!” she said.
Then Annie went back to tend to her poor daughter. I felt bad after talking with Annie so a little later, I stopped over to check on her myself.
“How are you doing sweetheart? I hear you are moving kinda slow today!” I said with a cheeky grin.
“I’ll be okay. Come next weekend I want to do that again!” she said.
“Well, we’ll see. I might have other games we can play!” I said.
“Ooh, I can’t wait!” she said with a smile. Yes, she was definitely Annie’s little girl, no question about it!
The following day was indeed Annie’s time with me and I was very much looking forward to our time together. But before the time came to pick her up for our date, I had some things to get. So I got up early that day and went out to get things ready for her.
I guess it was almost 2:00 pm when I got back home and our date was for 7:00 that evening. I spent the rest of the afternoon cleaning the apartment and tidying up. Around 5:00 I started getting ready to meet Annie. I showered, shaved, and got dressed for the date. I made sure everything was ready for the post-date fun as well.
It was right at 7:00 when I rang her doorbell. “Hi James, come on in,” Annie said, meeting me at the door.
“Hot damn, Annie, you look fabulous!” I said. Annie had gotten dressed to the nines for me wearing an ankle-length halter-top dress with a large deep plunge to show off her very generous bust, a side slit all the way up to the top of her thigh, and a sequin-studded collar. The dress was red with tiny glittering specks strewn about it to catch the light (and my eyes as well!) She wore silver strappy stiletto heel sandals to finish the look.
“Thank you, James, after the way you acted with Jenny, I knew I had to match her in the wow department!”
“Well, you sure did that!” I said, looking her over. She gave me a little twirl to show off everything and everything looked mighty tempting! “Boy the men in this town are gonna hate me – I have two gorgeous women all for myself!”
“Yes, it would seem so. But can you handle them both ... we are a handful you know!” she said.
I pulled her close to me. “Don’t you worry, sweetheart, I have two hands!” Then I kissed her deep and passionately. I had been waiting for this kiss all day and I took my time with it now.
“Oh James!” she gasped when I finally let her come up for air. “You certainly know how to take a woman’s breath away!”
“Well, you better get a lungful darlin’ ‘cause I’m only warming up!” I said.
While Annie got her jacket and purse I stopped by Jenny’s room to say hi. “Hi sweetheart, how are you feeling?” I asked.
“I’m doing better. Tomorrow, I should be back to normal ... and ready for more fun!” she said with a grin.
“Well tomorrow is Sunday, and since each of you will have had a night with me, tomorrow I thought we’d all do something together ... the three of us. I have something special planned for my girls, so get rested up!” I said.
“Oh, really? The three of us?” she asked inquisitively.
“Yes, and that’s all I’m saying for now. See you tomorrow!”
“Not fair!” she huffed. I laughed at her.
We left after that. Annie left some money on the table with instructions to call and have a pizza delivered for her dinner.
As we stepped into the elevator, Annie turned to me, “So where are we going tonight?” she asked.
“Well, after Jenny was so taken by the restaurant last night I thought you might like to see it too. So I made another reservation to take my other girl there!” I said.
“You don’t mind eating at the same place two nights in a row?” she asked.
“No, the food there is great and they have a wide menu. Besides, my appetite is for something a lot sweeter and tastier than a steak!” I said. Annie blushed because she knew what I meant.
We drove to the restaurant and got there at the perfect time once again. Annie was just as taken with the lights and the atmosphere as Jenny was and I was pleased that both of them enjoyed it. “Oh, James! Oh, it’s so beautiful!” she said, putting her hands to her face.
“You certainly are,” I said. Annie turned to me and then caught my meaning and blushed. Even in the dim light of the lights and candles, her blush was beautiful.
Dinner was wonderful and Annie was excellent company. We enjoyed our meal and then headed home for “dessert”! On the way home I told her that I had some surprises for her when we got there.
“Surprises?” she asked. I knew Annie was up for just about anything, but she was a curious, nosy little slut, and telling her I had a surprise waiting would drive her nuts!
Just to tease her some more, though, I suggested we go for a drive for a bit. “Umm ... okay, I guess. But what about the surprise?” she asked. I don’t think she was really thinking about going for a drive and I kinda threw her for a loop. But that’s half the fun of it – keeping her off-balance and guessing!
I knew of a little park that was rarely used anymore. The park was pretty overgrown and there had been talk it would be landscaped for a subdivision soon. But for now, it would be perfect for my needs!
I parked in a spot where it would be hard for passersby to see the car. “So what are we stopping here for?” Annie asked.
I smiled and turned to her. “Because Annie, you look so fucking hot and so beautiful in that dress that I simply can’t go another minute or another mile without kissing those soft red lips!”
I met her halfway across the car interior and kissed this beautiful, sexy woman with all I had. I wasn’t ready to use the “L” word just yet, but I did care for her very much. I had grown very fond of the “girl across the hall” and I wanted her to know it.
We kissed with all the need and urgency of a couple of teenagers making out in the family car before Mom and Dad found us. While our mouths were busy, our hands naturally found something of their own to play with – Annie’s hand found my cock and mine found their way to her amazing tits. We kissed and pawed and panted over each other until neither of us could stand it anymore.
“Please James, take me home and fuck me! I can’t wait a moment longer! I need you inside me NOW!” she said.
Since I was of the same frame of mind myself, I dropped the car into gear and took the quickest route home that I knew of. Annie barely let the car stop rolling before she jumped out and we literally ran for the door of the apartment building. Annie got to the elevator before me (hey, she had a head start!) and we went straight upstairs and straight to my apartment.
Once safely inside the apartment, we made a beeline for the bedroom leaving a trail of clothing like breadcrumbs along the way. If there was an emergency, the fire department need only follow the trail of clothes to find us!
She went straight to the bed climbing up on it and waiting eagerly for me. I came in and saw her there, sprawled out and looking at me impatiently.
“Don’t you want your surprise first?” I asked.
“Oh damn! I almost forgot about that! Yes! Yes, please!” she said, sitting up suddenly. I smiled and reached behind one of the sliding closet doors and brought out a large paper bag. I brought it over and set it down in front of Annie.
“I didn’t wrap it or anything since it’s not a birthday or Christmas present,” I said.
She was too interested in what was in the bag to worry about wrapping paper anyway. She reached in and pulled out a pair of sheepskin-lined leather wrist cuffs.
She looked at them and then to me. “You mean ... these are ... OH JAMES! OH, I LOVE THEM!” she squealed with delight!
After that, she dumped the rest of the bag out onto the bed. There was a matching set of ankle restraints, a leather-covered ping pong paddle, a soft leather cat-o-nine, a red ballgag, a blindfold, a pair of adjustable nipple clamps, a gold bullet vibe, and a rather impressive fake cock vibrator.
“All these things ... are for me?” she asked in wonder.
“Well for us ... to play. If you want to that is,” I said.
“Of course I want to!” she said. “But how did you know?”
“That you were into this kinda thing? I didn’t really. But I know you are a kinky little minx so I figured it was pretty good odds!” I said.
“I would say VERY good odds! I never told you but I have always fantasized about being tied up and forced to do things ... forced to suck cock, forced to take it up the ass, even gangbanged while being tied down. Oh God, James just talking about it has my pussy humming!” she cried.
“I kinda thought so. After seeing your reaction when I called you slut, I figured this might be a path you’d be interested in!” I said.
“Interested? James if you don’t tie me down and have your way with me right this minute...” she said.
“Okay okay! Jeez and I thought I was supposed to be the dominant one here!” I laughed.
She lay back on the bed with her arms up and the corners of the headboard ready to be tied. I put a wrist cuff on one wrist, buckling it down tight but not too tight. Then I put her arm down by her side.
She looked a bit confused but accepted it. I followed suit with the other arm then I moved to put the ankle restraints on. I reached under the bed where I had stored the ropes and brought them out. I tied one end of a rope to the D-ring on her wrist cuff ran it down to the bedframe where a half hitch held it in place there and ran the remaining rope to the footboard tying it off there. The same method on the other wrist had her arms pinned down.
Then I moved to her ankles. Because of what I planned to do to her, I needed those legs out of my way so she couldn’t clamp them together or block my way. I took one ankle and brought it up and over her to tie it to the end of the headboard behind her and then I did the same with the other ankle. Now her legs were high in the air and well spread, her arms kept her from sliding up and her legs prevented her from sliding down.
One final rope going back and forth a couple of times over her stomach would keep her from bucking upwards. She was firmly bound and helpless!
“Mmm, you look very lovely my dear ... good enough to eat!” I said. Her resulting groan made me smile.
I reached for the ball gag next. “Now let’s see how those pretty red lips look wrapped around this ball gag shall we?” I brought the gag to her mouth. Open up my sweet slut!”
“But how will I suck you co-AACK!” I cut her off the moment she opened her mouth wide enough to accept the gag. I pushed it in deeply to set it and quickly buckled the strap behind her head.
“Very attractive, my dirty little slut. Soon you will be drooling adding to the sexy picture! Now let’s see how we can decorate those magnificent tits. Oh, I have just the thing!” I said, lifting the nipple clamps up for her to see. She got a concerned and worried look in her eyes until I showed her they were adjustable. “See I can make them as tight as I want ... or as you need.”
Annie’s nipples were already pretty hard just from the excitement of this whole scene so it didn’t take much pinching and tugging to get them fully hard and erect. Once they were, I put one clamp on the right nipple adjusting the tension until she moaned and squirmed a bit. I would tighten it further as she got used to it and her nipples got numb.
Once I attached the second clip, I tested them by pulling up on the chain. I pulled hard enough to lift her massive globes up and she squealed from behind her gag.