Would You Fuck an Older Woman? - Cover

Would You Fuck an Older Woman?

by Tony Tiger

Copyright© 2021 by Tony Tiger

Erotica Sex Story: A sixteen-year-old boy can be surprised. This one found it very delightful and a real growth experience.

Caution: This Erotica Sex Story contains strong sexual content, including Mult   Teenagers   Romantic   Sharing   Polygamy/Polyamory   Interracial   First   .

Carmena surprised me. I was over doing her lawn like many times before. I was hot and sweaty and wearing only some tattered denim shorts. She brought me some water and I was startled that she was wearing only a rather thin robe. Her breasts were vaguely visible but the nipples stuck out clearly. I’d never seen her this bodily visible before. My crotch started swelling like any normal sixteen-year-old-boy’s would.

Then came the phrase I would never forget. “Would you fuck an older woman?” I was stunned and couldn’t answer immediately. She smiled and waited.

“I ... I ... I might. Depends on the woman,” was the best I could muster. I drank some of the water to calm myself. Then she opened her robe and I saw what I’d thought about many times. She was Latino and a mother. What lovely rounded and slightly sagging breasts. What a curvy body even after birthing two children. What a nicely decorated crotch with curly black hair. What a smile and pretty face topping it all. My addled brain output, “Do you mean you?” She laughed a bit as she nodded.

She knelt down and undid my shorts to let my swelling cock jump out and show off. Grasping it she kissed and sucked the swollen head. “This is quite nice. It seems interested.” Hell yes, it was.

I was almost paralyzed. She led me into the house and to a shower which she put me into with her presence under the water to help. Damn, I’d never thought about such a great activity. We dried each other and she led to a bed where I was laid down next to her luscious body. This was a much better situation than with any of my teen partners and a much more stimulating body too. Soon enough I was between her thighs and pushing in and pulling out of the finest pussy I’d ever felt. She wasn’t just laying there to let me masturbate in it like my teen pieces had essentially done. She was really participating in the mutual stimulation and making it clear her tits and other erogenous body parts wanted and loved the attention. She had a big orgasm like I’d never felt from a teenie and my own felt like my balls were going out through my buried dick. Wow!

As I laid there panting she talked to me. “Thank you. You are only the second man to do this with me. I needed it to take away the possession of my pussy from the man I am divorcing. Now it is mine again. I’ll never forget you and I hope we do this often too. What do you think?”

“I sure hope so! I bet I have a lot to learn too. What do you think?”

She gave me a kiss that used her tongue much better than any I’d ever had and said, “It would be quite enjoyable to be a teacher, I’m sure. Let’s figure out when you can be with me.”

I got home from school about four o’clock and her kids did too. The oldest was eleven so he would be put in charge of the seven-year-old for an hour while she came over to my house to “tutor” me. My folks didn’t get home from work until six at the earliest so that was great. On most weekends the kids went to be with their dad so Carmena and I could spend time together at her house. I got used to being in the presence of a lovely naked woman! She was doing somethings sexy for the first time in years she told me.

It wasn’t just rutting after a while. I learned about developing affectionate feelings to go along with the physical closeness that we did a lot. She held me just for closeness sometimes when there were issues in her divorce and she felt lonely. I wished I could spend more time with her. Spending the night in her bed would be wonderful but couldn’t happen since our relationship had to be kept secret.

When the legal stuff finished and she was officially single we did celebrate but something changed. She told me that now she could date and there was a man who wanted to take her out to get to know her. I had to ask if that meant she might have sex with him and she held me close as she said it could happen but I wouldn’t be excluded. She said, “There are things that I need a partner to do on dates. I’ll have you babysit with the kids when I go out and I also want you to realize that you can be dating too and I really want you to. That’s part of growing up.” I had to absorb that.

She kept no secrets from me and I knew about her dates, even meeting them when they picked her up when I was there to babysit. One thing that happened was her taking me to bed after she got back after a date. I wondered if she was thinking about the guy as she was screwing me. My dates were pretty chaste so far. No hot chicks but still a lot of fun.

Then it happened. She got back from a date that I babysat for and he didn’t leave but she sent me home. My sleep was restless. When I looked in her driveway the next morning the guy’s car was still there.

That was a Friday night and I went over to see her Saturday after lunch. She was in a robe and promptly took me to bed. She tried to seduce me as usual but I had to talk and was pretty blunt. “Did you fuck him?” She blushed at that.

“Yes I did and I liked it. I’ll probably do him again too. I want you too and right now. I couldn’t care for you any less, believe me, just like if you have another lover. This new for me too so work with me, please.”

I had lots of feelings as I touched and kissed and licked and filled her pussy knowing another man had been there just a short time earlier and probably more than once since I had been in her after school the day before. Objectively my cock couldn’t feel any difference as I moved inside her but my mind sure was thinking a lot about it. I had to realize though that it was new and different for her too, having only her third sex partner and now two on the same day, even only hours apart. She clung to me as we copulated and she held me close after we peaked. Her voice was soft as she said, “We did it three times but I didn’t get any climaxes like we have. I was kinda tense and more concerned how you would feel than I expected. Can you tell me?”

I kissed her and looked into her eyes, “Carmena, I love you and don’t want to give you up but think I can understand your needs. This is new for both of us, I realize.” She kissed me hard and shed some tears.

She shared anything and everything about the relationship with the new boyfriend and our own lovemaking continued to be good.

A wife on the next block needed yardwork done too since her husband was often gone for days to work. It wasn’t long before she asked the same question as Carmena, having gotten my name from her. Ruby was also Latino but in her early fifties and married about four years for a second time. What do you think I said when offered another big-titted experience? Sure she had more wrinkles and a thicker body but lots of enthusiasm and experience which she loved telling me about. “My husband doesn’t want to know how much fucking I’ve done even though he enjoys how it makes me do him so well. He knows I need it while he is gone and doesn’t object but also doesn’t want to hear anything about it. I’m glad you do. I sure enjoy what Carmena has taught you.”

I was enough for her and she fucked the daylights out of me after I did her yard work and paid me too. I was always amazed at how good these older women could make me feel. There was no reason to date for sex, that’s for sure, but it did nothing for my social life. Was there any way I could combine the two enjoyments?

My dear Carmena helped. Feeling a little apologetic for fucking now two other men as her dating life picked up, she introduced me to a young single woman from her church. Rosita was twenty but looked younger and had just broken up with a fiancé when he was cheating on her. They’d been fucking and she was getting horny so Carmena had an answer for that. Me.

She was gorgeous. Nice tits and long dark hair with a seductive smile. We quickly found activities to do to get acquainted and I just waited for the question. Of course I said “Yes” and our clothes came off. I went slowly and gently the first time and she started out anxious but relaxed a lot.

When I focused on her very hairy crotch to get acquainted I had to use both hands to part the abundant dark curlies so my tongue could do what I knew women especially liked. The moment her twat was tongued she squealed and shivered. I found out that was the first time ever. Her orgasm soon after I started it was, as she told me, one of the best she’d ever had. Her fiancé never tried to do what I was doing on our first intimate encounter. She kissed me to taste herself and loved that too.

I positioned her over me and that was another first. As she sank down on my ready rod and I put my hands to work fondling and treating her firm and well-shaped breasts she murmured “Why didn’t he ever want this?” She was able to get herself off again and I let go in her not long after. She laid down on top of me and cried. My question got the answer, “I’ve missed so much. Thank you and Carmena.”

My questioning revealed that her ex was the first and only man she’d gotten intimate with and that only because they were betrothed. He apparently just stuck his cock in as soon as he could get her lubricated enough to do so and made no effort to get her orgasm to happen. She now felt that losing him was a blessing, not a sadness. When could she get together with me again? Outside activities were not important as a prelude she said shyly. I did suggest she check with Carmena about trimming her pubes so access was easier for me and that really embarrassed her.

She was so sweet and smart that I really connected with her as a person and out physical closeness just cemented the rest of the times together. She really blossomed there too, doing some research on the web and timidly asking me to show her some nice porn so she could expand her horizons in that domain. No mention of my connection to Carmena which continued along with Ruby which I don’t think she was aware of.

I had developed at least warm feelings with all of them which I realized made the sex much more special and satisfying. There would be a sense of loss if any of those connections were ended but I did wonder how I could keep all of them going. It was a scheduling problem sometimes even now while I did yard work as a good reason to be at some places. Winter coming would cut that back a lot though. Hmmm.

Two days later we were in bed again. Rosita claimed to be eager to show me her neatly trimmed crotch but I knew it was a lot more than that. There was no pretext as my tongue set her off and she pulled me inside a very wet snatch to get her off that way too. Then she wanted to stay close and ride me for an extended time, getting off again before I spurted all over her cervix. From the murmurings I heard as we coupled she was being driven by the ancient urge to reproduce even though she knew she was using birth control. I sure hoped so!

I was the kind of man she’d want as a father to help raise her offspring. Her culture for millennia was not shy about having an abundance of them. The current world did not support that but some urges are built in and not easily changed. She wanted even more of my sperm sprayed deep without realizing why beyond the immediate pleasures. I didn’t know how to explain that to her so just enjoyed the very interesting rides as she quickly developed her manifestation of the powerful urges that were surfacing in her. I wondered how long I would be a sufficient resource to meet them.

In spite of what many would consider my “tender” age I’d learned a lot for my closeness with mature women. Sure enough, a couple of months down the road Rosita had something she wasn’t sure how to ask me. I encouraged it and she stumbled with this new thing. “I’ve met a man through work that wants to date me. How do you feel about that?”

I replied with a question, “How do you feel about him? Is it just as friendship to do interesting things together or do you feel sexual attraction too? Don’t ever be shy about telling me the whole story. We don’t have any commitment so I appreciate you talking to me about it.”

We were immediately post-copulation when she brought this up and I felt her pussy twinge as she struggled with the best wording. “I feel attracted to him as maybe more than a casual friend. He’s good looking and is sort of affectionately friendly like I remember my ex starting out. That makes me cautious though.”

I hugged her. “Good. I know that a person can feel affectionate to more than one person, as you know. I’d like it if you would tell me how things are going, though, and I can certainly give you a man’s viewpoint if you want it.”

Later I realized I had a different feeling for her than with the much older women. I was getting a stronger affection for Rosita. Was this the beginnings of love at my young age? Even if it was, I couldn’t do much more with it that I already was. Or could I? I decided to tell her if this new friendship got really going, but maybe I should tell her now to affect what she did or wanted to do with him.

A few days later we had just made love when she told she that she’d had a hot makeout session with Mauricio. I gathered he was Latino. They’d gotten as far as fondling genitals but without fully undressing. She felt that if that happened she’d for sure want him where I was right now but wasn’t ready for that. Thoughts of me as it was happening helped to hold her back.

 
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