Oh You Poor Man

by Tony Tiger

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Mult, Consensual, Romantic, Heterosexual, Fiction, Interracial, First, Pregnancy, Voyeurism, .

Desc: Sex Story: Compassionate sisters succor sexually deprived men of all ages and situations.

The first time I heard those words was on the second date with Rosie. I’d been advised by my buddy that she was the best way to rid myself of virginity. She taken his and several others he knew.

It had taken a month to get the first date with her and three weeks to schedule the second. She was obviously quite popular.

Wanting to make a good impression I had splurged on an expensive dinner and theater production for our first outing. Rosie did invite me into her small apartment afterwards and we sipped some brandy as we visited a bit. She finally shooed me out saying she needed to get to bed.

As I walked back to my car I realized that I hadn’t asked her for another date. When I was in sight of her apartment door I saw her greet another fellow with a rather hot kiss. I remembered her words about “getting to bed”. Obviously not alone.

On our second date we spent more time at her apartment and she responded readily to my attempt to make out. It got rather heated and her hand went to my crotch. Feeling my swollen prick, she uttered the Title words, followed by “Look what I have caused. Let me do something about it.”

My pants were unzipped and pulled down and her mouth skillfully released my prostate’s contents into it. I then got the first “cum kiss” ever. I had cupped her tits through her clothes during this. Once again, there seemed to be some time pressure and I lingered outside as a different guy was greeted and admitted.

On our third date I offered to fix dinner at my place and watch a new release DVD that she was interested in. After the meal we settled in to view this chick flick. It was almost soft porn and my pecker was swelling as she made body contact with me throughout the viewing.

We made out as the credits rolled and I got more aggressive with my hands. No opposition discovered. She pulled back and asked, very directly, “Are you a virgin?” I nodded.

“I thought so. Oh you poor man. I want to fix that right now if you are willing.”

I wanted to scream “Yes!!!!” but controlled myself and said, “Oh, that would mean so much to me.”

We quickly got naked. I was entranced as her body was revealed. She had light olive Mediterranean skin with dark areolae and fairly long nipples. Although her legs and armpits were shaved, her pubic hair spread down her thighs a way and up towards her navel. It was trimmed so most of the curlies were gone. Her inner labia protruded invitingly from some slightly plump outer ones. The first non-family naked female I’d ever seen, and she was a beauty.

She got directly to the point. I hardly got any time with her nice tits before I was being pulled into hair framed heaven. My cock suddenly had some indescribably pleasant sensations. I’d expected a pussy to be warm and moist, but I was experiencing a hot, silky wet, velvety grip on my tool. Her hips began moving and I was squeezed gently and released as I entered and reentered this incredible place. She stared intently as I built up to a ball blasting finish. My cock felt almost pain-like shooting sensations as I emptied spurt after spurt into Rosie’s depths.

She held me tightly and gave me a kiss as she murmured, “I love having a virgin.”

I pushed up a bit and asked, “Do you get one very often?”:

This love angel looked up at me and said gently, “I’ll always answer questions honestly so be sure you are ready for the answers.”

I said, “I’m ready. Tell me.”

Her pussy squeezed my still-firm embedded organ as she answered, “About one a month. I love the joy in their face and knowing they will never forget me. Just like you won’t. BTW, what time is it? I have to be home by eleven.”

I checked and replied, “It’s ten.”

Emboldened, I asked, “Do you have another date tonight like after our others?”

I got that direct look again, “You are an observant one. I like that. Yes, I do. And for your information my late dates are overnight. There was one who left this morning plus one this afternoon. And I expect you will next ask if I have sex with them. Of course I do. So what do you think of that?”

I was hard in her again. I figured some of that silky feeling was from earlier copulations since I bet she didn’t use condoms with them either.

Without answering her question, I started thrusting and nibbling on her nipples and she responded appropriately. I did get her home just as her next date arrived. She introduced us and gave me a kiss before taking him inside. I jacked off until I fell asleep laying in the wet spot we had made.

It took a couple of months of persistence but I finally got to be an overnight “guest”. I’d been circumspect in my questioning, getting bits and pieces of information but putting together a picture of this interesting young woman. It was incredibly erotic, especially when I was directly experiencing her, to realize the number of males who enjoyed what I did, both currently and in her past.

Rosie was twenty-five and a widow for the past three years. Her husband of four years had been killed in a motorcycle accident that left her financially set if she lived modestly. She didn’t work but volunteered often. She’d been a one-man woman before and during her marriage. No children had resulted.

During her grieving time an astute older man who had also recently lost a spouse triggered her strong sense of compassion. She uttered her first “Oh, you poor man” as she held his head to her full and firm breasts. The scoop neck on that particular blouse let his lips find her sensitive nipples and it kept going from there. A newly empty place in her life got filled that night and frequently thereafter.

It was so soothing that other men easily flipped her emotional switch, and her social life and bed became quite busy. As we talked between passionate tumbles, she explained that she had realized that she was the owner of her body and no man, or male dominated society, was going to have control over it. Women were built psychologically and physically to nurture. She has a strong innate desire to do so. Her first post-marital lover helped her to realize that and she has studied it extensively. Nurturing men has become her avocation.

To allow the most natural experiences with the fewest side effects, she elected a tubal ligation two years ago and she is regularly checked for STDs. So far so good. Probably due to a more careful choice of partners than you might think. She will not date arrogant or self-centered men. Lovers must be reasonably intelligent, fairly introspective, and have a need she can fill, like my virginity. Recently divorced men or widowers are also good candidates. Age is not a criterion but good body condition is. However, she is currently ministering to a man in hospice with pancreatic cancer.

On hearing that I hugged her and said, “I think I am understanding you. That’s special!”

She beamed at me and said, “It is rare that a lover even admits to my other lovers. Usually they act like they don’t know, although they must at least guess. Your curiosity is uncommon and I like it, plus the fact that you seem very non-judgmental. That is so important to me.”

We talked and loved so late that she texted her morning date (it was Saturday) to cancel so I could stay till lunch. She did have an afternoon and an evening date that she wouldn’t defer, but asked if I’d meet her at church Sunday at eleven.

“Sure, what church?”

She told me the address of the Unitarian Universalist church. I’d never been there. She told me I was in for a treat. Then she gave her sexy grin and said there’d be more treats afterwards. We both got a preview of “cumming” attractions again before I left.

I read up on UU and discovered it was the church of choice for many of the founding fathers of this country. There was no established creed or dogma, but promoted the belief that there were many paths for spiritual development along with some tenets for moral behavior. UU provided a community of support for you no matter where you were in the process. I’d rejected the very structured and controlling religion of my parents. This would be interesting.

Indeed, it was. The minister (they do have ordained ones) spoke on how compassion is hallmark of all non-militant religions and seems to be a fundamental human spiritual component. Rosie squeezed my hand at several points during the talk. After the service she introduced me to the minister then whispered, “He was the older man I told you about. He has remarried since then so we are just friends now.”

This sweetheart wouldn’t let me take her to dinner. She had prepared a small feast modelled after the one in the vintage movie “Tom Jones”. She showed me that scene and then we copied it, finally rolling around naked on the floor with food all over ourselves. There was an old blanket down. I noticed a lot of what looked like cum stains on it. Probably were, knowing Rosie.

As she popped grapes from her vagina into my mouth, I quipped, “I don’t taste your date from last night.”

She laughed and said, “I rinsed it out good. Semen didn’t go with the rest of the menu.”

After she licked the chocolate sauce off my erection, I rolled her on top of me and slid right in. Cupping her fine breasts and taking the nipples between thumbs and forefingers as she loved, I requested, “Tell me what my favorite pussy has been up to since I was last up it.”

She grinned and teased me, “Your ‘favorite’, huh? Last I knew, I was your only.”

I laughed, “That word does not imply plurality. You are both only and favorite. So answer my question.”

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