Taking Cindy's Cherry
Copyright© 2022 by Master Jonathan
Chapter 1
Coming of Age Sex Story: Chapter 1 - Steve was called over to his girlfriend's house under "false pretenses" by the girlfriend's teenage daughter. Once there, the young girl asks him to be the one to take her cherry and make her a woman...
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/ft Consensual Heterosexual Fiction First Masturbation Oral Sex
About three weeks ago I was sitting at home trying to watch a little television. I had just finished dinner and was flipping through the channels to see what was on that night when the phone suddenly rang.
“Hello?” I said.
“Hi Steve ... this is Cathy. I was wondering if you could come over tonight? I really need you ... I’m so lonely and horny. Can you come over and help me out?” she said. I had known Cathy for years and we’d had some good times in bed together. Cathy was a hot, sexy piece and I always enjoyed fucking her.
“Sure! I wasn’t doing anything anyway. I’ll be over in a few minutes. Be wet and ready to play, baby!” I said.
I am quite fond of Cathy, who is a very attractive divorced woman in her forties, and she was always a hot sexy piece and a lot of fun – she enjoyed sex and she enjoyed a lot of different activities and games relating to it. Her ex-husband was an idiot for letting such a fine woman slip away from him, but oh well, his loss was definitely my gain!
Cathy had a daughter, Cindy, who was 17 now. I had first met her shortly after Cathy and I started seeing each other and a couple times since, but we usually made sure she was out of the house when Cathy and I had sex. Cathy felt a little awkward having sex with her in the house, so she would make sure Cindy was gone or just come to my place when we wanted some “adult time” together.
I arrived at Cathy’s house about a half hour later. Cathy lived in a nice three bedroom house in an upscale neighborhood – thanks partly to the very generous divorce settlement the court provided her with. Seems her ex-husband found another playmate and got caught playing in someone else’s sandbox! I parked my car in her driveway and walked up to the house as I usually did when visiting her.
But I was surprised when Cindy opened the door instead of her mother. “Come on in, Steve,” she said and I followed her into the living room. I noticed that all the blinds were drawn and soft lights were on, which I also found a little puzzling, since Cathy and I almost always go directly to her bedroom when I come over. Cathy is usually quite impatient and anxious to get to the fucking so this apparent “ambiance” was a little out of character for her.
Cindy took me to the sofa. “You can sit here ... I’ll be back in a minute. I have something I want to show you, okay?” she said. She seemed pretty excited about and so I said that would be fine. Cindy was a pretty good girl and very friendly.
She left the room and, when she returned a couple minutes later, what she wanted to show me was obviously her very sexy body, clad in nothing but a skimpy black negligee, tiny thong panties that just barely covered her pussy, thigh top stockings, and sexy black high heels.
Now I will admit that I, on occasion, miss the subtleties of the fairer sex, but even I could see what she had in mind here. Not all the details necessarily, but the general direction she wanted this to go at least.
“Mom is out of town until next week. We have the house to ourselves,” she said, coyly. Then she sat on the sofa right next to me in her delightful virtual nakedness and told me what was on her mind.
“The last time you were here I cut class at school and snuck back home. I-I watched you and Mom making love, Steve. I’ve seen how happy you make her whenever you come over – she is like a changed person every time you come to see her. She might be sad or depressed or just in a foul mood, but when you come over she is happy and giddy and grinning like crazy for a couple days afterwards. This last time I asked her what it was that made her so happy when you came over. She and I had a long ‘girl-talk’ that night and she confessed that it was you and what you do to her that puts a smile on her face.
“When you left after your visit last time, Mom was in complete ecstasy. She enjoyed sex with you more that day than she has ever enjoyed anything. And it showed – even I could see it on her face and in her disposition.
“Steve, I have had a couple boyfriends and we have made out a little – you know kissing and petting and such. I’ve let them play with my boobies and rub me under my skirt or down my pants. But I’m a virgin – I have never had sex and never had anything in me except my own fingers. I’ve also never seen a ... man. I just didn’t feel like anyone was the ‘right one’ for me. I want my first time to be special and wonderful. You only have a first time once,” she said.
“Yes, I agree your first time should be special Cindy,” I said.
“That’s what Mom says too,” she said, “Steve, if it’s alright with you, I would like for you to be my first and take my cherry. I want you to do the same things to me that you did to my Mom that day, and make me feel the way you made her feel. I’m sorry I had to trick you like I did, but with her out of town, I thought this might be my only chance to find out what I’ve been missing.” she said looking down at her hands in her lap.
“Well, Cindy, tricking me was probably not the best way to go about this, but I understand your situation. At least you were honest enough to let me know the deal before getting too involved in it. Does your mother know that you have ‘made out ‘ as you say with your boyfriends?” I asked her.
“Oh yes. We have had lots of talks about boys and sex and love and stuff. And I’ve been on birth control pills since I was fourteen. Mom makes sure I take it with my vitamins every day,” she said.
I sat there on the sofa and thought about the situation for a bit. Cindy is the daughter of one of my lady friends, and even though Cathy and I see each other pretty regularly, neither of us has made the leap to an exclusive relationship.
Cathy is still leery after her divorce and I am happy with what I have with her. I don’t see a lot of other women – she keeps me pretty well oiled up so even though we haven’t claimed exclusivity and are free to date whomever we want, we still see each other more than anyone else.
Cathy is also aware that her daughter is sexually in her prime and has no objections to her experimenting with her sexuality apparently – even providing her with birth control pills. The situation was unusual, but I saw no real reason to turn her down. I looked at her again and seeing just what a beautiful young woman she was and how sexy she was in that outfit, my mind was pretty much made up.
“What size bed do you have in your room, Cindy?” I asked her.
“I have a regular full size bed. Not as big as Mom’s queen-sized bed, but bigger than a kids bed.” she said.
“Show me,” I said.
Cindy got up and smiling held out her hand to help me up. She clasped my hand and led me to her room. As I followed Cindy up the stairs and down the hall to her bedroom, I couldn’t help noticing how beautiful her ass was, especially peeking so nakedly out from under the hem of the negligee.
I had a fleeting thought about doing something about it but decided to stay with more standard sex. The next time, if there would be a next time, I might introduce her to some different activities, but that day, I was primarily going to give Cindy the best time I could, as I would for her mother.
Once we were in her bedroom, she pulled down the blankets on her bed. “Is it better to have a sheet or blanket to cover ourselves with?” she asked me.
“Neither one. It’s warm enough in here that we don’t need anything to keep us warm and it would just get in the way. The negligee you have on is nice to get a guy interested, but remember the more you wear, the more he has to take off. But unwrapping a present can be part of the fun as well!”
As I spoke, I was removing my shirt and shoes. Cindy stood there as if waiting to be told what to do. I could tell she hadn’t figured on making it this far and didn’t know what to do next.
I sat down on the edge of her bed and drew her closer to me. I pulled her in between my spread knees and looked up into her young, pretty face. “Cindy I know you feel nervous and scared. It’s perfectly natural to feel that way right now. Your first time having sex with someone is a big deal and an important step.
“But we will take it nice and slow and go as fast as you want to. If you tell me to stop, I will. If you want to go faster, that’s up to you. I only want to make you feel good and make this whole thing a wonderful experience for you. Understand?” I said, holding both of her hands as I spoke.
“Yes, I understand. Thank you,” she said with a little smile.
“You’re welcome, baby. Now why don’t we get you out of that pretty outfit – we don’t want to get it wrinkled or messed up!” I said smiling. She reached up to begin taking it off but, I put my hand on hers. “Why don’t you let me do it for you, honey. A lot of men enjoy undressing a woman. It can be exciting for both of them. Let me show you.”
I started off by kissing her. This first kiss was tentative and unsure, but as we kissed some more she began to loosen up. My hands roamed up and down her sides as I kissed her and with each move upwards I got a little higher. Before long Cindy had her arms around my neck and our kissing had gotten more passionate and, for her at least, more urgent.
I moved my kisses to her neck, planting a trail of hot, burning kisses going down her neck as the young girl began moaning her delight. I slipped the thin spaghetti straps of her negligee off her shoulders, kissing her where they once were. As they fell to her upper arms the flimy garmet slipped from her breasts and she instinctively covered herself with her arm.
She looked at me a bit embarrassed at her reaction and I smiled, gently pulling her arm away. I pulled the negligee the rest of the way down until it puddled around her ankles. I helped her step out of it, leaving her in just her panties, stockings, and heels.
Cindy, like her mother, was a very beautiful, very sexy woman. While Cathy was a blonde, Cindy had brown hair. Both women shared amazing bodies – Cindy got her mother’s large breasts, an attribute I found so delightful in Cathy. I was eager to see if these young breasts were as sensitive and responsive as the mother’s were.
When I would lick and suck on Cathy’s generous tits and thick chewy nipples it never failed to flood her pussy with a copious flow of sweet juices. I was hoping that Cindy had gotten the same sensitivity in her ample tits and hard young nipples as well.
“Why don’t you climb into bed honey and lie down on your back,” I told her.
“Shouldn’t I finish getting undressed first?” she asked.
“Actually, leave the rest on ... you look really sexy like that,” I said. Cindy smiled and then got up on her bed like I told her laying on her back.
I was wearing just my pants as I lay down beside Cindy and placed my hand gently on one of her luscious breasts, which was full and vibrant, with silky smooth skin. “Now remember Cindy, this is all about having a good time and enjoying each other okay? So when I do something, let me know how it feels or how it makes you feel. I want to know if what I do is making you feel good. That way I can keep doing it or change to something else if necessary,” I said. She nodded her compliance.
I began caressing her full firm breasts, gently squeezing the pliant flesh and hefting the globe, feeling its weight. When I rubbed her nipple with my finger, it was soft and almost rubbery, and I softly pinched the nub, toying with it to see how it responded. I was pleased when it grew thick as my teasing it continued.
I knew I would need to spend quite a bit of time kissing and licking and caressing her until she was ready for something more advanced. I intended to eat Cindy’s pussy until she climaxed, which I know was one of the things she heard me doing with her mother, but I would have to increase her sexual excitement before doing that.
Usually when I got together with Cathy, she was already fairly horny and after kissing her face and throat and licking and sucking her breasts, I would eat her pussy until she came. I expected to do something like that with her daughter now, but take longer on the foreplay, especially stimulating her lovely breasts. That was certainly more than alright. Cindy has a beautiful body and, as she said, we had until next week.
I kissed her again, but this time Cindy responded to my kiss by thrusting her tongue forward to meet my own and we rubbed them together. She had apparently rinsed her mouth out while getting ready for me, because I could taste a hint of mint.
The more we kissed and the more our tongues played together, the faster her breathing became, which meant she was becoming more aroused. When I thought the time was right, I moved down her body until I reached her chest.
I glanced up at Cindy’s pretty face, and saw how relaxed she was. The slight smile and the partially closed eyes, told me she was enjoying what I was doing to her, although she might not have known just what that was.
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.