Kris... My Sexy First! Pt. 01

My name is Jack. I've been alive 60+ years, and have been happily married for the last third of those 60. She is a good woman, sexy and we used to have regular, fun sex. With fantasies, light bondage, watching porn and getting really turned on. Occasionally she dress up in stockings, silk with lot's of glossy lipstick and we would suck and fuck each other nicely.

The last couple of times when she was away of business or family travel, I would dress up in her stockings, silk skirts and a sexy bra and blouse. She even had large feet (size 11womens) and I could actually get in to one pair of her heels. Tight and they hurt but I felt SO sexy. Some of my best jack off cums were in stockings.

A couple of times she would let me dress up for her and she would dress up also. She had admitted in the past to having some girl on girl play with a roommate so it fed her desires and fantasies too. If felt so incredibly to kiss her with my wet red lips and her glossy red mouth. Then things became boring and eventually she lost most interest in sex. Stress can do that to folks. Eventually I got to thinking as I explored porn and our sex life faded. I was getting turned on by she-male videos and becoming curious about sucking a lady cock. I always thought it would feel so good to feel a cock grow in my mouth and feel it slide in and explode with cum into my mouth and on my face. But these days in a small town it is hard to find a trusted safe partner for an old man.

That is when I began to look at some websites for horny old men. Also read a few stories here in Literotica and became curious and wondered if I could find a nice "girl" to play with and explore my desires. It took a few failures but finally I connected with a local girl that preferred older men and seemed honest and was so sexy in her photos. She was 27, about 5'11" and about 150 so a nice fit body. We emailed for a couple of months back and forth exchanging stories, desires and just learning more about each other. Her name was Kris. And she had the perfect petite body, small tight titties and nice clean shaved cock that looked incredible. Not too big or no too wide. So sexy.

My wife was going to be away soon for a family visit half was across the country so I would have some alone time so Kris and I planned to get together. She requested that I do not dress in stockings and such just be me. That was easy. But as the day approached I became very nervous and anxious. On the day we were to meet I woke up and was oddly relaxed and excited. It was winter and here it gets dark about 6pm so to keep it discreet, we agreed that she would come over to my home about 7pm.

About 6pm I had showered, splashed on some cologne, put on a nice white shirt, dark jeans and silky boxers underneath. Then I had my first glass of wine. Fastest hour in my life passed and I saw her car pull in to the driveway. To keep things from being controversial she arrived in male jeans and hair and brought her outfit and makeup with her to get ready here. I took her coat, gave her a nice hug and a glass of wine. We sat on the sofa and made small talk. But we were both obviously anxious.

"Why don't you show this girl to the bathroom so I can get into something a little more sexy, and pretty" said Kris with a smile.

"Why of course, this way."

I picked up her bag of goodies and walked with her upstairs to the master suite that I had prepared for the moment. Candles everywhere, lights really low. And had a speaker playing quiet smooth jazz music for background.

"Here is the bathroom where you can do your magic. Shower or take a nice bath if you desire. I put a little bell on the counter, all you have to do is ring it a little when you need anything or when you are ready for me to come up. But take your time and relax. You will find another bottle of wine chilled in here if you need it."

Kris blew me a kiss and said "ok sweetie, I hope you will like what you see."

"Oh I know I will and I hope you do as well." and I went downstairs to get a refill on my wine and maybe watch some porn to bring up the anticipation a little.

About 30 minutes later, I heard the little bell ring. I made sure the door was locked, turned on the football game on TV with the sound muted. Hopefully if someone being was being nosey, they would just think we were watching the game.

I journeyed up the stairs, slowly walked into the bedroom and saw Kris standing in the bathroom door. WOW! Short black skirt, stockings, heels and silky white blouse. I could just see the lace on the top of her black stockings. She was paying attention on our long chats when I told her about my dressing up with my wife. She was wearing the same outfit I had put on. The closer I get I notice her beautiful short blonde hair, and beautiful red shiny lips. So incredibly sexy and right here with me!

"You look incredibly beautiful, wow."

I said as I went to her, put my hand on her chin and kissed her lightly and sensually. She felt sensuous and soft. As we kissed, Kris slid her hand down my waste to my belt buckle. She undid it, unbuttoned my jeans and slid them down as I stepped out of them. I held her tight. My hands explored her beautiful tight young body with my hands moving over her hips around to her ass. Then down to her legs under that nice skirt.

While we were standing there and I was exploring her body, she was doing the same with me. She went directly to my growing cock through my boxers. I still at this time could not see or feel any sense of there being a cock on this lovely girl. But I knew and hoped it was there. She had a cock and I wanted to feel it in my mouth. I wanted to smell it, taste it, suck it.

She lead me to the bed and said, "Just sit down Jack... let me relax you a little. If at anytime you are uncomfortable just let me know, ok sweetie?"

"Yes beautiful" I replied.

With that, as I sat on the edge of the bed she unbuttoned my shirt and ran her hands across my chest. It felt to relaxing and incredibly sexy. I could not believe this. I had a beautiful young woman in front of me kissing my chest and licking my nipples. My cock we certainly about to break through the part in my boxers. Then we kissed again. Her soft lips met mine and that was all it took. My cock stiffened again and peeked through my boxers as I sat there.

She felt it with her elbow, glanced down, smiled and said "hello there."

After we both finished chuckling, she kissed me again then mover down to my hard cock. She wrapped her fingers around it and just held them there. I can't explain how good that felt. It had been so long since anyone but me had wrapped fingers around my dick. It pulsed again. Kris moaned then mover her lips with their red gloss closer to it. The gently licked the head, moving her tongue around it slowly. Then she wasted no time in parting her lips and very very slowly covering and consuming me. Again a sensation that has been a long time since I had felt that kind of magic.

She moved up and down on me. Sucking, licking and moaning with each throb of my cock. I reached around her head in my lap and placed my hands gently on the side of her head, holding her as she bobbed up and down on me. This was the most turned on I had been in way over 10 years.

About 5 minutes of the warm wet mouth on my member and I could cum, but didn't want to yet. I had other plans for the next few minutes.

"Come up here sweetie, I want to kiss you and taste you with my cock still fresh out of it."

Oh my I could taste what I imagined was a different flavor than before in her mouth... and it was delicious. She had been on her knees by the bed, I held out my hand to help her up. So sweet and feminine her moves and attitude were. Beautiful inside and out. She sat on the side of the bed, legs together looking sexy. It was my turn to kneel by the bed.

I ran my fingers slowly over her silky top and around the small perky tits. It felt so good feeling her skin through the silk. I sensed that she had no bra on as I didn't feel anything around her breasts as I touched them. I leaned over to her, kissing the side of her neck while I slid my fingers up the back of her head and through her pretty hair.

We kissed again, and it was even hotter than before. It felt like a level of sensuality that I had never felt. I began to unbutton her top. Working my way down and her blouse stayed together until I finished the last button, then I ran both hands from her waste up and parted the silky fabric. My first glance at the perfect pair of small tight breasts. I ran my fingertips around her nipples and I could see her breathing was speeding up as she began to quietly moan in pleasure. I kissed them for several minutes and they became wet from my mouth and slippery which seemed to add to the sensitivity. I then began kissing between them, then moved down to her belly. So smooth and firm.

"If it's okay with you I would like to see and taste that nick cock you have? I have thought about this moment since the first time we chatted online. I hope that the things I like receiving that I would hopefully know how do do this? If not please offer tips if I need them?" I said smiling.

"Of course Jack, but you know what... I have also been looking forward to being your first so just relax and lets both enjoy the moment?"

I ran my hands on the side of her legs from the knees up to her thighs. She let out a little gasp as I moved just above the stockings and felt her bare skin. Gently massaging her smooth legs. I moved across the top of her legs to the inside of those wonderful legs. I could feel movement as the black panties she had on were beginning to stretch a little with her arousal. As I kissed the inside her thighs I would also move over her bulge and kiss it through the softness of silk. With my first touch I could see it pulse and grow.

"Oh wow that feels really nice" Kris said with short breath. She was breathing quicker and hopefully enjoying herself.

"I hope you feel as sexy as you look and as good as I feel." I said, relieved that she was enjoying herself.

I took my hand from her legs and softly ran it along the side of her her bulging panties. Kris surprised me by taking my hand and held it on her cock. I took the hint and wrapped my fingers around it as best I could through the fabric. She then took her hands and held the side of my face around to the back of my head. While she pushed me in to her cock, I parted my lips and kissed the silk covered dick. I felt it pulse as I pressed my lips on it.

Kris then moved one hand and put a fingertip into the waistband of the panties. I pulled back a little and watched what she was doing. I wanted to get a good look at my first cock. She pulled the top of her panties out and down over her cock as it sprang out and twitched with excitement.

It was beautiful, so much better looking than mine. It was pretty hard, not longer than my 6" cock but it was thinner. Nice small head, and the skin on the shaft was very very smooth and shiny. It kind of hung in the air as it rested on the panties. I got closer to it, I could see it was mostly hard from what I could guess? I licked the bottom side of the head and it really pulsed then and Kris let out an even louder moan than before. She liked it!

Here I was, about to suck my first cock and I was not worried, nervous or scared at all. The passion of the moment took over my emotions and while I was looking this beautiful cock inches away from my face I just had to get it in my mouth. I kept my lips tight as the tip touched them, then very very slowly parted them and slid her cock in to my mouth. I was going so slow so I could feel every pulse and throb of the cock. Slowly allowing it to enter my mouth while running my tongue along the bottom side of it.

"Of fuck baby, that feels so good. Incredible... so nice I love it... hmmm oh yes baby" Kris spoke with an out of breath voice.

She was really panting now. I let it glide into my mouth deeper and deeper. I never thought I would be able to get this much of a cock in my mouth but it filled my mouth and I just started to gag a little as it was almost all in. I moved up and down a time or two. The feeling of this cock in my mouth throbbing is even better than I had anticipated and dreamed it would be.

"Do you want me to take these panties off sweetie?" She asked.

"Yes please yes!"

She had been sitting on the edge of the bed as I leaned back on my knees and she stood. I slid then down over her heels and sat them aside. I looked up at her... ran my hands up the back of her legs to her ass. Placed my hands over her curved and tight butt. She was completely clean shaven and smooth. Very smooth skin and a nice small nut sack. Very very hot. Her cock was jumping up and down with excitement so while holding her ass, I found the head and slid it back in to my mouth. Pulled her close to me, driving that hot shaft into my mouth. In and out as she fucked my mouth. She was moaning and grunting more and more. I felt her dick get even harder. It is not a big cock but damn it is HARD.

"Oh damn baby, this feels so good so yeas you are very very good at this and I like it a lot. Yes that's it... of damn baby. Sooooo goooood. Not sure if I can hold off. The way you are sucking me want me to cum. Think you are ready?" She quickly asked.

I pulled back and her dick popped out of my mouth. I was still on my knees and she leaned over and gave me the hottest wettest kiss.

"Mmmm I can taste my cock in your mouth and it makes me want to cum even more. Are you ready for my cum baby?" Kris softly said as she looked at me.

"Yes yes I am ready to taste and feel your cum.. and I want it in my mouth. I want to feel it shoot and hit my throat." As I said that she grabbed the back of my head again and pulled me into her again.

I guided her dick in to my mouth, and I gently put my hands on her little ass and she began to fuck my mouth again. It had softened a little as we were talking but as soon as it entered my mouth I felt it grown quickly. And soon again is was back to it's rock hard state, and thrusting in and back, in and back. Kris had put her hands on the side of my face again and was also pulling me into her as she fucked. Her moans were getting shorter and louder.

"Oh yes Jack, I am going to cum baby yes feels so good baby, don't stop. Suck my sexy dick and take that cum for me please baby please."

I was ready for it and hoping for it. She was close... I could feel her pace get steady and firm, then I felt the base of her cock throb and swell.

"yes baby, feels so fucking good and yes baby I'm cumming for you yessssss yessss yessss!"

With that I took as much of her cock as I could, and felt the first burst of hot cum hit the back of my throat. I felt my tongue sense another load pulsating up her shaft and squirt went another shot of cum. I was surprised how easily I swallowed it, but a good friend of mine had told me to put it all the way in when you are sucking cum out of a cock. I slid the throbbing cock half way out of my mouth and I felt a third shot of cum that landed on my tongue. Again surprised with the taste. It was so good, and salty in a hot kind of way. I pulled it out for a breath and a fourth shot landed on my lips.

She smiled down to me and smiled as I had a bit of cum on my chin. Kris leaned down and gently kissed me right where the cum was and she gave a nice sound of pleasure as she tasted her own cum. What an incredible experience. Sucking my first cock as so much better than I had hoped it would be.

And that was just the first part of the evening...