Oh You Poor Man

by Tony Tiger

Copyright© 2016 by Tony Tiger

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

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

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.”

She moved slowly on my shaft as she told about the middle aged married man who had spent time in her bed in the afternoon. His wife was an invalid and couldn’t have intercourse. She knew about and had met Rosie.

Her evening date had taken her out on a friend’s sailboat. They had anchored before dark and skinny dipped for a while. At dusk the grill on the cockpit rail was lit and some steaks prepared. Then they went below to “play”. It was a tight fit but all of them had fit into the main berth together.

I interrupted, “ALL?”

“Oh, my date doesn’t know how to sail so the boat owner was there too. They are both introverted tekkies who gave me their virginities. I’ve known the skipper for a while too and I’ve been on the boat before. Maybe you’d like to go sometime?”

“Perhaps when I’m ready for a threesome,” I replied.

“I don’t keep count of how many orgasms that I or my dates have so don’t bother to ask. Anyway, they got me back to shore in time for a shower and church. So there you have it. Happy?”

I gave a couple of upthrusts as I explained, “I’ve realized that I couldn’t have been aware of any of that unless you told me. I DID like hearing how sexy you are. I don’t know why but it makes me feel closer to you and want you more. Is that crazy?”

She kissed me hard then put her head beside mine. In a whispering voice, “No one has ever said that to me before and it makes me happier than you can imagine. You are getting to know me like my first lover and no one since. You are not crazy, just awful damned special. I’ll fall in love with you if I’m not careful.”

“Would that be so bad?” I whispered back.

She sat up and gave me a serious look, “I’m not ready for love. I have a lot of compassion to give yet. You would be very special if you just came along for the ride as my very best friend for now. That would show compassion for me and I think you are very capable of that.”

I nodded and we consummated our coupling, then set a date two days hence for our next rendezvous. It would seem like a long time to me, especially after today’s revelations. I WAS falling in love with this unusual woman, sexual promiscuity notwithstanding.

When we were next joined at the crotch I asked her what she had been up to. Hearing my choice of words, she quipped, “Don’t you mean what’s been ‘up’ me?”

I laughed, “Not necessarily. I like you as person, not just as a genital owner. So catch me up.”

Carefully omitting sexual references, she told about shopping and a museum visit as well as a call from her younger sister who wanted to visit. She asked, “She will be here this weekend so I haven’t made any dates. But I’d like you to meet her and do some fun stuff with us.”

I was, of course curious as to what she meant by “fun stuff” but canceled everything else for that time.

Rachel was a beauty who looked very much like her sister. I found out that she had been engaged for a year with no wedding date set. I figured that pretty much limited sex for the weekend. The two gals together were a bundle of energy and I chauffeured them hither and yon on Saturday. Both of them were touchy and friendly to me all day and I did like the attention. At lunch Rachel made a point of rubbing her legs on mine under the table and giving me a wicked smile as she did so.

Finally, back at Rosie’s apartment she poured us all some whiskey. I toasted two beautiful women, Rosie toasted my friendship, and Rachel toasted to more and better friendships. Rosie then explained that since her small apartment only had a king size bed, Rachel slept with her. She then added, “And I think there is room for you too. Rachel would like that. She needs some of your compassion. Her fiancé has been in the middle east for over a year. Don’t worry. He is a realist and knows her needs and trusts her commitment to him. What do you say?”

I went to Rachel and gave her a solid and wet kiss, “I’d be honored to give you whatever you need. Just as with your sister, my body is yours.”

Rosie stood up too and said, “Let’s get naked right now!”

So that is how I got into the second pussy of my life. Their bodies were quite similar. Although nowhere near as experienced as her big sister, Rachel gave a helluva fun ride and broke into tears after a magnificent orgasm. She’d warned me that it had been months and to not think I was hurting her when she let go. I’m glad she did. Rosie didn’t thrash and shriek like that, but maybe it was because she had such frequent releases.

She woke me twice in the night and repeated her performances. Rosie whispered to me to just give all I had to her sister.

I awoke after dawn with a mouth engulfing my soft cock. Rosie was cleaning all of the combined juices off. I had to piss so she went with me and held it. Then we went to the living room and I ate her to her climax. My dick was dead for a while. My sweetie kissed me and thanked me for being so helpful. Would I stay with them until Rachel left? Hell yes!

Rachel caressed us later in the day as Rosie and I joined in lovemaking. It was too gentle and caring this time to be labelled “fucking”.

That night as I was gently thrusting into Rachel spoon style, Rosie’s hands were exploring both of us, even bringing her sister to an orgasm and cupping my balls as I put my love fluid in her for that last time.

Rachel was in a great mood as she left and asked if she could visit every month until her betrothed returned. Rosie rejoined with, “You want to cut into my game or what? I gave up three dates while you were here.”

Rachel understood her sister and my role with her. Her answer, “I could stay with your best friend which wouldn’t crimp your style. You could still see me when you had a chance, and he’d have someone to have fun with while you were busy elsewhere.”

That actually made sense to everyone and a specific weekend was set for the next visit.

By now I knew Rosie’s half dozen regular and three occasional lovers by first name, and how they had come into her life and bed. She never sought them. Circumstances delivered the needy males to her attention.

I would hear about dinner with Joe, a retired man with a pitiful pension. She bought his dinners as well as provided her special dessert. Yuan was a young Taiwanese husband struggling to establish himself in the US so he could bring his wife and family over. She would stop by his rooming house twice a week after he got home from work. Arturo suffered from fear and depression as an illegal alien sending what money he could earn to his widowed mother and wife in Mexico. His visits were as irregular as his work schedule.

Not all were charity cases. One in particular was an obscenely wealthy computer genius who was so reclusive that he lived on a private island which he rarely left. He had been persuaded to meet Rosie by his best friend who had been transformed from a similar shy nerd into a man confident enough to find his own girlfriends. On Thursday late afternoons she drove to a nearby airport and his helicopter took her to his island. Dinner was followed by what she referred to as “training sessions”. This had been going on for six months and she was about to “graduate” him.

Her “pussy power” had persuaded him to hire Arturo part-time at double the prevailing wage for such work. Arturo was often returning from the island as she as going so they would do no more than smile. He knew what was going on but her “student” remained quite unaware.

Rachel’s first weekend visit arrived. She found my place easily and started stripping as soon as the door closed. She was HOT to trot! There had been lots of erotic messages with her betrothed since her last visit here.

He was pleased that she’d found someone trustworthy but was, of course, terribly envious. He’d reported that a surprising number of married soldiers of both genders had a similar understanding with their spouses. They themselves were granted similar freedom but the male/female ratio at their bases was heavily skewed. Some female soldiers “helped out” multiple men. Could he have some pictures?

I wasn’t as horny as Rachel and could keep up with her demands because I was usually waiting at Rosie’s place when she returned from the island on Thursday nights. She often needed the good boffing she didn’t always get from her student lover. That got me ready for her sister.

The two of us had a good time Saturday doing other things in addition to screwing rather frequently. Rachel commented on Sunday morning that she didn’t think that she and her fiancé had ever done it so often in a day and half. She emailed some discrete photos of her body alone and with me touching it in various way and places with a variety of my body parts. They even got me hot when I saw them. He would go wild.

We met Rosie at church and went out for dinner. Cock and pussies were pretty well fucked out so we just snuggled naked with a gal on each side of me. We idly fondled each other’s bodies as we talked. Rachel related our activities in considerable detail, showing her sister the pictures we sent.

Then Rosie told of her dates, who and where they went and how often she’d been laid. It had been an unusual busy time. The first guy got a quickie right after he got off work. The next was a dinner-fuck followed by an overnighter who got pussy before, during, and after sleeping. Lunch and an art gallery visit with another lover finished in bed. Saturday night was out at the island again where her student and his best friend learned about threesomes. She was a bit sore and not very horny.

Rachel and I had recovered, stimulate by Rosie’s amazing sluttiness. Rachel shook her head, muttering, “I don’t think I could ever do that!”

Rosie grinned, “You could if you got in shape. Never say never.”

Four weeks later it was the Thursday before Rachel’s next visit. I had just barely sunk my prick into her student’s semen when Rosie’s phone rang. It was Rachel so she answered it.

I could hear the wailing that came from the phone, “HE’S DEAD! THEY JUST CALLED ME. OH MY GOD! HE’S DEAD!” Her fiance was a battle casualty.

That’s guaranteed to shut down coitus real fast. I said, “Tell her we’ll be there as soon as we can.” I made the hour trip in forty-five minutes with Rosie on the phone with her distraught sister the whole time.

The sisters held each other and cried. I fixed some stiff drinks and we all sipped at them as we cried and talked. I’d never been told that Rosie had introduced them when she was dating the man who later became Rachel’s fiance so there was a very intimate connection.

I took a personal day and Rosie cancelled four dates over the weekend. Rachel need our full love and attention. She finally cried herself to sleep. Rosie was awful teary as we finished what we had started earlier then joined Rachel. We were once again three to a bed.

Rachel woke in the night and demanded that I take her, holding me so close it was sometimes hard to breathe. I didn’t ejaculate but she didn’t even notice, falling back asleep after she orgasmed with me trapped in her arms and legs.

The next time she awoke she insisted that I fill her with sperm. As I pumped into her she moaned, “Give me a baby! I wanted his baby so bad. I love you too so knock me up...” And so on. Rosie lay beside her with arms around the hurting sibling.

That was her refrain all the time I stayed there. She was reasonably composed by the time I had to leave and Rosie stayed on. Rosie called and emailed frequently. With the insurance proceeds Rachel could quit work and said she wanted to come and live with me. My compassionate self couldn’t refuse the hurt young woman I cared about.

There was plenty of sex, of course, and she insisted I still see her sister as I was used to. I was wallowing in pussy for the first time in my life. But the theme of wanting to be bred was constantly out there. I found a counselor to work with her and that seemed to help.

We were a couple but we weren’t. More like friends-with-benefits that lived together. Then one day that changed drastically. She announced that she’d had her birth control implant removed. She wanted to still live with me but had decided that the kind of compassion her sister administered would be good for her too. She was meant to be a mother and God would choose who would impregnate her. I knew it would take a while for the implant to wear off so I didn’t resist as she coaxed two loads of baby seed from me.

Rosie wasn’t any more thrilled about this turn of events than I was, but was unable to dissuade her sister from this quest. The best she could do is introduce her sister to guys she knew had little or no sperm and fill them in on the program.

I started getting more and more sloppies from Rachel and I hoped my seed would get there first, at least. I really cared for her but was that enough for marriage? Rosie did her best to help me and her sister.

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