I wasn’t going to miss this chance for nuthin! As I scooted forward on my knees I aimed my steel-hard cock at the glistening and dark-hair-trimmed target that I had lusted after for ages. Here it was, inviting me, finally!

My mushroom head made contact with the hot wet lips standing open like tiny tent flaps and I almost came from that. I pushed in carefully, not sure how fast to embed myself in this brand-new territory. She moaned softly as I took deeper and deeper plunges. When our pubes met I almost came again. She murmured, “Whose cock is this? It ain’t Steve. I can tell cause it’s thicker. No matter, it feels good.”

I guess I’d better back up and tell how this came about.

Sheila, the girl I am now fucking, is my new step-sister. About three months ago our parents got married and she moved in. She is eighteen and I’m sixteen and my good friend Steve is right in between. She and Steve started screwing about a month ago and she is still dating some guys she knew from before. I’m sure she is spreading for them too because she is such a sex hound. She started flashing me her tits and not wearing panties around the house and I got beaver shots all the time. Our parents go at it a lot and Sheila will jill herself right across from me when we could hear them doing it.

She and I have bedrooms on the lower level of the house which has its own entrance because of being built on a hill. Her boyfriends can come (cum) and go without our parents even noticing. I can hear her getting laid, especially when I’m in the shared bathroom between the bedrooms. I’ve jacked off many times listening to her sex noises. She has no modesty around me either, waltzing naked into the bathroom to pee or shower even if I’m there. More masturbation food. Oh, she’s an average size brunette with c-cups and a nicely trimmed bush.

Back to the present. It was Steve’s idea and plan how to lose my cherry. He’d gotten a little kinky with Sheila and would tie her to the bed and put a blindfold on her, then ravage her a few times. This time he’d already screwed her and signaled me to tap her pussy for my first time ever. I’d already cum watching him hammer that horny hole so I could last a while, I hoped. He’d coached me so I sucked her upturned and hardened nipples as I slowly savored that hot grip on my shaft. It was best to not think about that slippery feeling from his cum. Just like he told me, when I pushed deep and moved my pubes against hers to rub her clit she moaned and gripped me with her untied legs.

When she shook and yelped in her orgasm, I slammed hard and unloaded the best ejaculation of my life. I soaked for a few minutes then pulled out and Steve was ready for another ride. She whimpered as he sank his ready rod into her still-tingling twat. I cleaned up in the bathroom and headed for bed.

Sleep came quickly, but it was interrupted sometime in the early morning darkness. Who wouldn’t wake up when somebody got in your bed and pressed their naked body against yours! And especially when they reached for your cock, which quickly jumped to full attention. I heard my stepsister’s voice, “This feels like the second cock I had earlier tonight. Am I right?”

I sheepishly said, “Yes, it was me.”

She chuckled and said, “Would you like some more?” I would! Since my cock was ready for action she pushed me on my back and climbed aboard. This was another new experience, having her on top, and my hands got busy caressing her body in eager exploration. She was so slick inside that I was able to last quite a while before my balls boiled over. Once again I heard those noises she made when she felt fresh semen blasts.

I guess she wanted to talk for a while and I hoped that meant we could fuck again when I got hard. “I’ve been wondering when you were going to make a move on me,” she stated, “That was very creative of you two, and fun, but all you really needed to do was ask. You know how much I like to fuck, so why wouldn’t I want to do it with you too?”

I was stuck for a reply and she just giggled, and kissed me, and then moved down to suck my cock hard again. A third new experience for me and I think she sensed it, asking, “Is this your first time? It seems like it is, and if so I am honored.” I nodded.

She spooned me this time and we fell asleep together. Sometime, quite a while after dawn, her mother walked into my bedroom and said, “When will you two be ready for breakfast?”

Sheila answered casually, “We need a shower and then will be right there.”

I was stunned and it took a moment before I could ask, “I’m amazed that your mom is okay with this.”

We hustled to get in the shower and she explained, “My mom has seen me in bed with lots of guys and she even shared boyfriends with me if I didn’t have any good partners available. She would probably fuck you too if it was okay with your dad. It’s good to try people of different ages because you can learn a lot from them.”

Breakfast was just as normal as can be and Sheila announced that she had an afternoon date to go to a ballgame and might not be back until late. I kept myself busy the rest of the day but stopped to jack off twice with the memories of the last 24 hours. Steve came by for a visit too and we talked about the little stunt he had set up. He thought it was hot, and even more so because she figured it out, and fucked me again. He had done her twice after I left and then she came to my bed for the rest of the night. Steve and I were both amazed at what a hottie she was.

About 11 PM Sheila walked in my room, took off her clothes, and snuggled up to me like the night before. “Ya want some more used pussy?” I reached for it and it certainly was. I guess I need to get used to pre-lubricated poontang when I get it from her. I rolled between her welcoming thighs and dipped into her swamp. It wasn’t long before I added mine to what was already there but she didn’t come. “That’s okay. I’ve already gotten off a few times this evening. It just felt good to have you in there.”

We knocked off a much longer piece using several positions before breakfast. I asked and she told me about her date. It was an older guy that she’d been screwing for a couple of months whenever he could get away from his wife. Since she was being so open I asked her how many other guys she was getting naked with.

She laughed at that question, or at least the way I put it, “I don’t get naked with all of them. I am usually commando, which means I don’t wear underwear, and sometimes I just bend over and pull up my dress or drop my slacks and they stick it in. But I know what you mean. Besides this guy, who shall remain nameless, and Steve, there is the older man in my old neighborhood that I used to work for. He was my first and I double-team him and his brother about once a month. That’s enough cocks for now but I’ve had as many as six guys on my string. It wears a girl out just keeping track of who and when. This seems to be a comfortable number and it’s great having you and Steve so handy. You seem to be a quick learner so I’ll teach you how to make any woman happy.”

I had my own topics to discuss, “I sure didn’t know women were so horny or could cum so much. Also, you felt different this morning than the other times we’ve done it.”

She grinned, “Up till now you’ve only had ‘sloppies’ from me. All the man cream soaked in and you got to feel the natural me. I like it both ways.”

Steve had a date with her tonight and as she was leaving she told me, “Don’t jack off while I am gone. I want you and Steve to double-team me without a blindfold when he brings me back here. Big loads get me off so save up all you can for later.”

She got her wish. Steve and I kept her pussy full of fresh sperm all night long. It was a good thing it was Saturday because she slept until noon and happily complained that she could barely walk. At lunch her mom grinned at me and asked Sheila if she might borrow her “boys” sometime.

I thought that was just a joke between mother and daughter until Dad went off on a business trip for a week and by Wednesday my stepmom was pretty horny. Sheila announced that she was going to spend the night with the brothers and I should invite Steve over to help take care of Mom like she had asked. I got a woody instantly. I was quite concerned until stepmom reassured me that Dad knew about it.

Stepmom was a hottie too. She liked her guys clean so she showered with each of us while the other one sipped on some wine and thought about what was just ahead. She was also quite casual about nudity so I had some good glimpses of her pendulous breasts and furry crotch. It was a damn sexy sight for two young guys and she admired our arousal indicators with her hands and her talented mouth.

I’d expected that she would choose one of us to fuck her first but we got a surprise. I was slightly shorter and thicker than Steve so she mounted me reverse cowgirl and kept her legs wide spread, urging Steve to also enter her pussy on top of me. We were both amazed how it worked and it was a little weird, but erotic as hell to feel our shafts alongside each other. Neither one of us guys lasted very long and she made the same sounds her daughter did as we erupted inside her. As we pulled out she quickly slurped the residual cream from our shrinking cocks.

Yet another surprise when she demanded, “Who is going to clean my pussy this time?” When neither one of us jumped at the opportunity, she pointed to me and said, “Family goes first. Get busy!” With the tone of voice she used, I didn’t dare disobey and discovered it wasn’t bad after all. She wiggled and giggled and climaxed again before I was done, then congratulated me on a great job.

Steve and I took turns enjoying various parts of her body separately and together. She could give great tit jobs but didn’t particularly want anything up her ass. After each of us had spunked her pussy again, Steve got to use his tongue down there. I was sure that Sheila would like that kind of attention too.

Her pussy was kept in excellent condition for Dad’s return on Saturday afternoon and I now knew at least one of the reasons he married her. While Steve stopped by to help when he could, I was the main man taking care of mom and daughter for several days. Of course, I didn’t complain but I did sleep whenever I had a chance.

Sheila and I were eating lunch when Dad got home and took stepmom to the bedroom immediately. We heard lots of noises and they didn’t emerge for couple of hours. That was when the whole thing felt a bit strange to me, and even more so when he thanked me for taking such good care of her. She had told me, by the way, one of the times we were copulating, that it would happen only when he was away. That was fine since keeping up with Sheila was already a lot of responsibility. I figure that very few boys my age were getting the quantity and quality of pussy I was blessed with.

For a person so young, Sheila sure had an imagination. She took me with her on the monthly visit to the older brothers she had mentioned. They wanted to watch her bang a younger guy and she wanted a foursome. Between us we managed to plug all holes since one of the guys was rather small-dicked and she would let him in her ass. It was a lot of fun, even when she was on one of them reverse cowgirl and she made me lick where cock and pussy came together. They did it to me to and held my balls as I pumped my prostate load in with theirs.

Sheila is making friends at college and says when she finds the right one she’ll fix me up with them. In the meantime I’m learning everything I can from her and from my stepmom when my dad is away. I don’t even date the girls at school since they seem so silly and Steve said the ones he’s tried have hardly been worth the effort. I’m guessing that anyone Sheila fixes me up with will be older and be pretty good at it like she and her mom are. I can hardly wait!

She and Steve and I were talking the other day. Sheila is working on a counseling degree at college and does girl talk with other students between classes. She heard from both single and married ones that the guys they take to bed could use a lot of improvement. Like I said, Steve and I are taking lessons from her, so I suggested maybe she should offer classes to teach their men how to fuck better. She laughed but said it was an idea she would bounce off her girlfriends. I also said that she could loan Steve and me as samples of her work. She laughed some more but I could tell she was thinking about it. She could use the income, that’s for sure.

She brought up the topic again a few days later and said that one of the women had a different twist on the idea. Maybe Steve and I should teach the women how to train their current man or men. They were concerned that if they invested in some guy, he might ditch them for someone else and the money would be wasted. Good point!

One Friday evening Sheila brought home Wendy, a classmate who was a couple of years older. After we were introduced, Sheila said that Wendy did not have a boyfriend and had been disappointed in bed by the few that she had tried. She wanted to take us up on our sample offer.

I queried, “Do you want one or both of us?”

Wendy was a slightly chubby blonde with light skin and her blush was quite obvious. She stuttered, “I think one would be enough and I’ll try you first.” We noticed her use of the word “first”. We would wait and see what that implied.

I took her to my bedroom and we undressed each other piece by piece. Then I suggested we take a shower together so we would be at our best. She liked that idea and we explored each other’s bodies with soapy hands and towels.

One of the things Sheila had taught me was to take my time, especially with a new partner. I kept the pace slow, encouraging tactile and oral stimulation until her pussy was very wet and reeking of the female mating scent. She moved to the missionary position so I entered her that way first but after a while rolled us over to put her on top. Her soft breasts swung nicely as I encouraged her to ride me and I gave them lots of stimulation, enough that she orgasmed. Apparently unused to this much exercise, she was tiring so I rolled her to a scissors position, stroked her to another orgasm, then filled her with semen. She squealed when she felt the hot juice.

I stayed inside her and asked her reactions. She had never had sex like that and loved it. Now she understood what all the fuss was about and thanked me over and over again. She could hardly believe that I was only sixteen! Would I ask Sheila to come in and talk to her?

Sheila emerged in a little while and asked Steve if he wanted a piece of Wendy. “What normal guy would turn down a chance at new and reasonably attractive pussy?” I thought. Sheila said that Wendy had wanted to screw Steve also but was very concerned that that would make her a slut. After Sheila related some of her adventures and that she just felt like a real female, Wendy was reassured and we could hear the noises she was making all the way out where we were.

Wendy gave both of us guys a deep kiss when she left and hoped she’d have another chance with us. We were noncommittal because this had not been discussed with Sheila yet. This session was supposed to be sample, not an introduction to a relationship. It was pointed out to us that a hungry woman who was well satisfied didn’t want to let it go, so lessons could cause some attachment issues.

Sheila had some counseling courses already so she decided to start with small groups, exploring individual needs and common issues. That would also give her an opportunity to get to know the women and their personalities so we could avoid the ones that could turn into problems.

That seemed to work. Steve and I each acquired students that we met with twice a week and Sheila was instructor and mentor. Wendy stayed with me and I also had a married woman older than my stepmom. She turned out to be a real tiger. Her body showed evidence of the three children she had, all of whom were older than me, and she was ready for almost anything after so many years of vanilla and guilt-ridden sex. Her husband had an affair and she did too and this training was her condition for their marriage to continue.

At each session she fucked me dry and left to do the same to her husband at home. With Sheila’s help, she’d primed him to be turned on by her just-fucked pussy and absorb everything new that she had learned that time. It went so well for her that she terminated the lessons after a month and they were going to swap mates with her sister who had been hinting at that for years. She gave us a gift certificate for free night at a nice hotel as a tip.

Wendy kept on longer since she hadn’t found a suitable boyfriend yet and swapped off with Steve once in a while. My next student was a young Asian woman who was studying in this country with her husband. He was gone much of the time and she was very frustrated, not only with the low frequency of sex but the very short duration, leaving her unsatisfied most of the time.

Mei Ling cried the very first time I copulated with her for fifteen whole minutes, bringing her to two orgasms before mine. This was sex like she only read about during two years of marriage. Sheila and I gave her some reading material on the web she could share with her husband as a source for her new knowledge. Sheila taught her techniques for delaying ejaculation and I was the stand-in for her husband.