Taking Care of Dad's Business

by Tony Tiger

Copyright© 2019 by Tony Tiger

Erotica Sex Story: Young male orphan's adventures with his stepmother and several later female acquaintances.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Teenagers   Romantic   Sharing   Slut Wife   Group Sex   Orgy   Swinging   Pregnancy   .

Here I am, barely sixteen and an orphan. No brothers or sisters either. I’d be all alone if it weren’t for my step-mom.

My mom died from cancer five years ago. Dad remarried last year and Wanda is only ten years older than I am. They seemed to be in love and spent a lot of time in the bedroom, often slipping away during the day when Dad was home.

Dad died in an auto collision that was not his fault so the insurance and lawsuit settlements left us pretty well off. Dad had a small business that Wanda and I have figured out how to keep going. He’d hired some good staff which saved it.

The night after the funeral Wanda got pretty drunk. I helped her to bed and was trying to get to sleep myself. My bedroom door was open so I was completely surprised when she got in bed with me and snuggled against my back. I sleep nude and she was too.

Wanda is almost my height and at the high end of normal on the BMI scale. Her breasts are the pillow type and need a bra to fully show off their size and shape. Short blond hair on top and silky sparse muff. I have to admit I’d whacked off more than a few times after seeing her skimpily dressed or hearing her getting laid.

Anyway, those melons were pressed against my back which, naturally, filled my young cock to capacity. Then she draped an arm over me and her hand found it. That set off some basic reflexes I guess. I got rolled on my back and felt a hot, wet mouth engulf half of my hard six-incher. Why I didn’t blow my load right then I’ll never know, but I’m thankful I didn’t.

Wanda tried to climb on for a ride but she was still too drunk so she pulled me on top of her. I was too polite to refuse, as if I would have under any circumstance. Between the two of us we managed to get my cock into unknown territory. God Damn! I had no idea pussy felt like that. I shot my load rather quickly in that velvet grip but knew, from meat-beating experience, that I could stay hard enough to work on a second one. So I kept on pumping.

I must have been doing something right because Wanda, with her eyes closed began moaning and thrusting her ample hips back at my pushes. She began breathing harder and murmuring Dad’s name and how she was enjoying what he was doing to her. That was kind of spooky but somehow made what we were doing all right.

She clutched me and moaned and shuddered for a short time, then lay motionless, apparently asleep. It only took a few more strokes for me to empty my juices in her. I carefully pulled out and lay down beside her.

When I awoke she was gone and her bedroom door was closed. It was much later when she emerged, looking for the coffee I knew she would want.

She wouldn’t look me in the eye so I stayed quiet, having quite a few feelings rattling around inside me too. Breakfast seemed like a good idea so I got started on it. She made herself busy that day, avoiding me and the elephant in the room.

We watched a movie that evening and she drank more than usual but not as much as the previous night. Later, in the dark, she came to me again and I was a substitute for her lost love.

This time she got on top and I could explore the massive mammaries of my fantasies. I was surprised that I could get her to orgasm just by fondling, sucking, and pinching them. But then, I had a lot to learn about women and sex. Had I found a teacher? I sure hoped so.

She was still in my bed when I awoke and, after we both peed, I got my first doggy-style fuck. It was so hot to reach under and fondle those swaying fun-bags.

At breakfast she was ready to directly confront our intimacy and opened the subject, “I guess it’s obvious that we both enjoyed what happened. I’m not judging whether it’s right or wrong either. I just don’t know the answer to that question. There is a more practical issue though. I’m not on birth control because your dad was snipped. My period just finished so it is pretty safe right now. If we continue I need to get some contraception right away. So, how do you feel? Be honest with me.”

I felt brave and also trusted her. “Of course I liked it. I’m a teenage boy and have lusted for you since Dad brought you home.” She grinned, liking the praise. “When I’d hear you and Dad going at it I’d sometimes have to jack off.” A bigger grin and head nodding. “So if I’m have something you seem to need on a regular basis, how could I not volunteer to help?”

She came over and hugged me. “I am awfully used to frequent sex and you have done very well for a beginner. I’ll call my doctor right away.”

Wanda had an IUD put in the next afternoon. We held back until then but celebrated the acquisition with our first fuck with the lights on. The light from the bedroom window anyway. Wanda was a little shy about being visibly naked with me just yet but got over that when her arousal built. She obviously loved to fuck based on how often she and Dad had gone at it. My youthful vigor and quick recovery delighted her. I was thrilled that she was as horny as me.

I commented on her eagerness and she explained that she’d started sex pretty early and had a few good mentors. Dad had been captivated when she double-dated with one of his buddies. Then she explained that a double-date for her meant that she went out with two men at the same time. A date usually finished up with them all naked in bed or some other comfortable place. She loved outdoor sex and promised to take me to some places she and Dad had found.

She suddenly stopped talking and teared up. “God, I miss him. So many things remind me. Maybe that’s why it’s so important to me to be making love with you. Not that I don’t like you for you, but...”

I shushed her with a kiss and a nod. Thinking about the bit she had told me about her sexual history had my imagination and erection fired up so I went for the good stuff again. She shut up and screwed me right back. As my cock throbbed its cream deep in her pussy I did think about my own dad’s seed that had started me being put there so many times. It was a bit eerie and sobering.

Wanda hired a classmate of mine with a business major as a part-time order processing clerk for our business. Molly was a petite redhead with a long and wavy mane. Cute as hell with a sparkling personality too. I had to interact with her often when we were there after school.

She asked me to escort her to a school function and I had a great time so we would frequently do stuff like that together. I made no romantic moves on her since that part of my life was well handled at home.

One day she asked me to take her swimming. I knew a secluded stream pond where Wanda had taken me to screw outdoors. We took a lunch which we enjoyed between swimming sessions. Molly was wearing a very brief bikini which made me much more aware that she was an attractive female.

When we tired of swimming Molly wanted to work on a tan. She told me she had to be careful with her pale complexion but it could be done. Lots of sunscreen was needed and I was asked to apply it “all over”. She meant that, before she rolled on her back, she untied her bikini top and took it off, thus giving me an eyeful of her firm, nicely curved breasts with stand-up nipples. “I don’t want tan lines, so be thorough,” she said with a grin.

I saw her glance at my swollen crotch after I finished. Turning on her side to face me she asked outright, “Are you and Wanda sleeping together?”

I was tongue-tied and stuttered, “W ... w ... what m ... m ... makes you think that?”

She smiled, “Oh, several things. You two interact like a husband and wife and you’ve never hit on me. Every boy I’ve dated has tried to get in my pants by this time. Taking my top off was the final test. Your crotch says you’re not gay, so what other reason could there be?”

I said, “I’d rather not answer that question.”

She grinned, “I’ll take that as a Yes. Don’t worry, I’m not going to judge or reject you.”

When I dropped her off at home I gave her our first kiss. She changed it from a peck to a lip-lock and murmured, “There’s more where that came from” before disappearing inside.

When I related the day to Wanda she laughed, “She’s an astute young woman. I like her so don’t let what we have block anything you and she both want to do. And I’d be prepared for more if I were you.”

Right she was. Molly was quite professional at work but the next Friday she asked to go swimming again. This time, before we even got wet, she took off her entire suit and asked me to do the same. She eyeballed my erection and seemed to find it acceptable, with hard nipples and the sweet odor of aroused pussy being evident.

“I want you to know that I’m a virgin. Quite a few guys have tried to change that but they were either too immature or looking only for marks on their scorecard. I’ve held out for someone that I care for and who knows what they are doing so it can be a happy memory. I’m offering it to you unconditionally, like lovemaking should always be. Are you willing to help out a novice?”

I took her in my arms and we were skin on skin. “I was a novice not very long ago myself and got some very loving attention. I’m happy to pay it forward. Let’s stop talking.”

Our lips and tongues were soon occupied with lots of things besides words. She tried fellatio with my guidance to just short of my ejaculation, then I ate her to a screaming orgasm. She had to recover from that before we continued.

Her maidenhead was a bit tough but I got through it and she soon felt the first semen deposit. It was OK inside, she told me. She’d been on the patch for a year, ready for the right situation.

We rinsed off in the pool and she was ready to ride me. This got her off again before I put more sperm in her.

When I took her home she was subdued but thanked me profusely. “I hope we can do this again,” she said quietly, “and I hope Wanda is OK with it. Will you sleep with her tonight?”

I noticed she used gentle reference words but answered, “Probably. And Wanda expected this to happen. Our relationship is more one of support than any romance. Neither one of us has any expectations about how it will go.” Molly nodded and kissed me goodbye.

Wanda wasn’t surprised and asked if I needed to stop screwing her. I told her that Molly seemed OK and we didn’t know where our relationship was going either so why change anything? I was very grownup-thinking as I said that. I knew she didn’t want to date so soon after Dad’s death just to get laid, and certainly not for love, but someday she would. Using her example, I would be just as understanding.

She hugged me and reached for my cock to see if Molly had left anything for her. It had been three hours since I last came in Molly so it was reloaded and ready. Now I had a basis for comparison and noticed the differences in women. All good, I decided as I treasured each experience.

Two years later things were going along pretty smoothly. Wanda was running the business maybe better than Dad had and enjoying it too. Molly and I were a tight couple. I was accepted by her parents and could stay overnight in her bedroom. Molly and Wanda were BFF with me as a common bond, and you can imagine my contentment alternating nights with them.

Molly had early on asked if she could watch me with Wanda who asked for the same opportunity in reverse. That led to some occasional threesomes. Again, a happy man. I was finishing college and my twenty-first birthday was near. When asked, I couldn’t think of anything I wanted or needed. “Surprise me,” was all I said.

Wanda was starting to say yes to a few dating opportunities. Having me to come home to allowed her to keep her dates platonic. That was very different than the last time she’d been on the dating scene when she met my dad. With no pressure from her hornies, she could concentrate on the other aspects of her date. I noticed she always had them on days/nights I would be with her and our inevitable lovemaking was sometimes more inspired as she told me about her encounters.

I often thought, as I was stroking deep between her legs and enjoying her luscious boobs, how the guy she’d just spent the evening with had no clue what happened after he dropped her off. I’m sure he wished he could be doing what I was! And I realized that, someday, some lucky guy, or guys, would be. Then I’d have to share just like she did with me. Maybe even have to deal with her going exclusive.

My birthday surprise was two-fold. The first part was that Molly and I were going on a week-long adults-only cruise. The second was that Wanda had found a guy she wanted to try in bed and would do so while we were gone. My jealousy kicked in and I talked to Molly about it as I absorbed this not-unexpected change. She had some ideas of how to help me through it since she’d been there.

Our cruise was in the Caribbean on a rather small ship which went to lesser visited, smaller islands. Big ships wouldn’t fit there so it was a less-crowded experience. Our cabin was small but we only needed it for sex, we joked. Neither one of us had travelled much so this was exciting, plus being on our own as a couple for a whole week.

The day trips were well planned and interesting. The food on board was good and there were plenty of activities to keep us occupied. We soon met another young couple and made friends. Some of the rooms had balconies and we could hear couples screwing out on them after dark. We opened our window and did it doggy as the night sea-breezes wafted over us.

Paul and Melody were another unmarried couple who clued us in about the pool area. After eleven it became clothing-not-required. We stripped and skinny-dipped. I kept my cock under control, helped a lot by our after-dinner fuck. Melody was a somewhat plain brunette whose small, cone-shaped tits somehow seemed to rub against me fairly often. Molly noticed and reciprocated with Paul.

She asked him to dry her off when we heard the dance music start. The lighting was very subdued but I could tell they left little space between their still-nude bodies so I asked Melody to dance. She pushed up tight and my cock got the message. When it got uncomfortable and projected between her thighs, she casually reached down and put it between our bellies.

After a couple of dances, I excused myself to dance with Molly. She did the same thing with my pole so I knew Paul was having the same reaction to the situation. I asked her if she liked the dancing and she just said, “Mmmmm”.

We took a break and I sat with Paul while the gals went to get drinks. We didn’t want to wave our woodies at the bar. I asked him if they’d ever done anything like this before, He responded, “No. We’ve only been with each other for a few months now. But we are curious. How about you?”

I answered, “Pretty much the same here. We haven’t talked about it but I think Molly is open to trying something new. She is far from a prude. I’m OK with whatever she is.”

Paul suggested, “Let’s keep dancing for a bit and I’ll suggest to Molly that she come to my room. I think Melody will go along if she sees it’s alright. We can get together again at breakfast.”

I grinned, “Sounds like a plan to me!”

That’s how it went after another round of drinks and body-to-body dancing. Melody’s nipples were hard as rocks and I thought I could smell hot pussy. When Molly came over holding hands with Paul and gave me a quick kiss before they walked off together, Melody gasped and clutched my hand. I looked at her questioningly and she nodded her OK.

We put on our robes and picked up our swimwear. It was after midnight and the ship was pretty quiet. When we entered my room she was very reserved so I went slow, sitting beside her on the bed and just gently putting my arm around her. She was shaking, probably from anxiety rather than lust.

I knew she needed soothing, “We’ll only do what you want to. No rush and no expectations. I know this is new to you and it kind of is to me too. Could we start with kissing?”

She looked at me with big soft eyes, “I’d like that. I’ve never been with anyone but Paul so I hope I’m good enough.”

I held both her hands, “There is no ‘good’ or ‘bad’ so throw that idea away. I know that I will be different than Paul and that is the part to celebrate.”

She relaxed a bit and the kissing helped a lot more. Her robe soon opened and her body responded to the touches of a new partner. Her hand found my erection and she got steadily hotter, soon begging me to “put it in”.

On my second stroke she convulsed in orgasm, “OMG, OMG, OMG!” She was soon begging me to cum in her and when I did she blasted off again, then got embarrassed about it. A perfect opportunity for much praise and I didn’t waste it. She beamed in the dim light as she lay under me.

She woke me twice in the night for more helpings of my cock and was clearly multi-orgasmic. We had to shower quickly to get to the agreed breakfast reunion. We ate quickly with few words, all eager to get back to bed with our original partners and share the experiences.

The door had barely latched when Molly displayed a still-reddened and wet pussy inviting me in. She was slippery with Paul’s spend and I had to struggle to keep even my well-drained cock under control, knowing what I was sliding in. She came quickly, muttering what a happy slut she was. I pumped my sperm in with all the others and then we talked.

Paul had been horny and considerate, exactly what she hoped for. His cock was similar in size but curved the other way so created some novel sensations. He touched her and moved differently. Now she understood a bit of what I experienced with two women, and why some women got addicted to a variety of cocks as Wanda had at one stage in her life.

That got us thinking about Wanda. Molly texted her and asked.

Wanda responded that things were going well and she had a happy pussy, even in my absence. That got me hard and Molly got me going with talk about what might be happening at home. Mischievously, she wondered if Wanda’s new beau would feel as good as Paul had. I made no comment but my balls did.

The women conspired at lunch and decided that we would swap as couples for the rest of the day. That meant that Melody and I went on the shore trip while Molly and Paul went scuba diving, something she’d always wanted to try. We couldn’t find them when we got back to the ship. My room was vacant so we got naked and fucked a couple of times, figuring that is what they were doing.

When we went to the pool, they were sunning so we swapped stories about our afternoons. I took Molly back to our room to change for dinner and plowed her recently fucked vagina. They’d done exactly what I’d figured. We both were amazed, and pleased, with how much we were getting laid with the stimulus of the new partners. That night we went to the pool late for skinny-dipping and, in a dark corner, watched our partners get it on with the other one before we took the new one back to our room.

The next day was the last full one of the cruise and we stayed with our own partners for activities and the usual afternoon screw. That night we swapped for the last time and there was a regretful goodbye. They lived a day’s drive away so getting together again was definitely a possibility.

As we flew home, Molly and I were pensive. We had changed and wondered how Wanda was doing. There had only been minimal communication so we all had lots to share.

The gals huddled for half an hour before I was allowed to join in. Wanda reported that her pussy was quite happy in spite of my extended absence, but did miss me and would get reacquainted later. She was thrilled to hear about our adventures and knew from plenty of personal experience that is was a good lesson for us individually and as a couple.

We would meet Phillip, her new guy, at dinner. He’d spent almost every night with her since she had seduced him the second day we were gone. He was a few years older, divorced with two small children that she had yet to meet. He was intelligent and financially secure, key criteria for Wanda.

When we were screwing later that afternoon, Wanda said his cock was shorter but fatter than mine. He could go a long time too. Nice variety to have. He didn’t know about me yet and she intended to keep fucking both of us. I was reassured. Tonight she’d bed him after dinner and then resume our usual sleeping arrangement.

When she came to our bed after he left, I was quickly embedded in his fresh fluids. She was still aroused and welcomed me avidly. As I pumped us to orgasm I recognized that this was by far the soonest I’d ever had her after another man. When she’d first come to me it had been almost a week since my father had seeded her. My very recent experience with Molly and Paul helped me handle some possessive feelings about this “invasion” of “my woman” even though I knew better. She seemed happy so that was all that was important.

The next morning at breakfast Wanda was already gone. Molly asked me my feelings about this development and I told her what had happened and what emotions were triggered. She looked at me intently as she revealed her thoughts and feelings. “At first I wasn’t real interested in screwing Paul but I wanted to stay sexually interesting to you. Wanda has so much of that and I felt kind of insecure. I knew you wanted to try Melody so I went along with it.” She lowered her gaze, “I was kind of curious though. It was more exciting than I expected and it gave me some perspective I needed. The sex wasn’t nearly as good as with you, in case you wondered.”

I cut in, “It was different both physically and emotionally than with me, wasn’t it?” She nodded. “I think what you are telling me is quite normal, so be OK with it. If you have another experience, just enjoy it, OK?” Another nod.

Molly was looking forward to meeting this new man in “our” life and I was pleased when she openly wondered if she’d like him and would Wanda share? I certainly couldn’t object and told her that might take some time to work out, depending on how open-minded he was.

A scholarship to a three-day seminar series was available and Molly qualified. An advantage to having two “wives” is that I never got the least bit horny while she was away, although I sometimes had to wait my turn. Wanda loved it, of course. She never got too much sex.

When Molly returned she wasn’t the excited bubbly person I expected. She even seemed reluctant to have sex with me. I’d expected an almost insatiable partner. I finally asked her directly what was going on.

She kept her eyes down as she answered, “I did a real dumb thing. The first day there this real cute and charming guy came on to me and I was very flattered. The short story is I screwed his brains out for two days. On the third day I saw him making the same moves on another woman so I broke it off. I moped around feeling very used and stupid.”

I put my arm around her, “Well, one way to look at it is you used him too. No harm done and you learned a lesson. Did you use condoms?”

“No.”

“That could be a problem. Let’s get you checked.”

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