Chapter 5: The Principal, Food Sex, Pregnant Anal, Fiancés and Fathers, Conclusion

Fall came, and the start of my senior year of high school. I struggled to think of ways I could keep my active sex life from distracting from school. I still wanted to be a good student! On the first day of school, I started the morning by walking down the hall and climbing into Sabrina’s bed, waking her up with anal sex, coming inside her quickly. I explained about how an orgasm would help me focus on my schoolwork. She giggled and told me that was silly, but she wanted a romantic secret-girlfriend shower with me, so we did that before getting dressed for school.

I couldn’t help it. My curiosity got the best of me. I pushed the button on my Plot Device as I was heading out the door to school.

Fifteen minutes into my first class, I got a note telling me to go straight to the principal’s office. I trudged down there. Behind the desk was Mrs. Herschel, who had been our principal for three years. She was in her early 40s, straight dark hair with bangs. She had a reputation for strictness and most of the students were scared of her.

“Sit.” she said briskly. “Young man, I heard a lot of rumors about you, during the last school year. Apparently, your behavior is sexually loose. You have several girlfriends in this school?”

I nodded. “Yes, Mrs. Herschel. My main girlfriend Lisa graduated last year and she’s at the City College now, but I have a few other girlfriends here at this school. One of them is Mrs. Okassian’s daughter Katie, who’s a sophomore this year, and a few others.”

She nodded. “And you are sexually active with all these girls?”

“Yes, ma’am.”

“Isn’t that going to distract from your academic performance, and theirs?”

“No, ma’am. I don’t think so. To start with, there’s only one of me. So each girl only gets a little time with me. Except for the other sex they have with their girlfriends, sisters and mothers. I can’t do anything about that. And there are a lot of girls.”

Mrs. Herschel shifted in her seat. “Ah. Ahem. So you are having sex with a good fraction of the female student body?”

“Yes, ma’am. And at least four of the teachers. I know that’s against the rules, but I promise we’re discreet about it. I almost never have sex on school grounds. Unless Mrs. Okassian is really horny, and she needs me or sometimes a couple other male students to satisfy her. We always do it in a locked classroom.”

“Natasha Okassian?” she said in amazement. “Well, she is a beautiful woman.”

“Yes. In fact, she’s pregnant with my child, and so is her daughter Katie.”

Mrs. Herschel’s voice was husky. “Well, I’m going to need you to stay very discreet. I don’t want a scandal.”

“No, ma’am. I don’t want a scandal either.”

“But you are obviously very sexual and virile. I need to know more about how you manage to have so many women available to you.” Her eyes fluttered, and she paused.

“Mrs. Herschel? Are you OK?”

“Please, call me Deborah. I’m fine, it’s just that my panties are pulled down and I’ve been masturbating since you walked into my office. Could you please come around the desk and fuck me now?”

“Yes, ma’am.” I grinned. “I think it’s going to be a good school year. But I’m going to need you to suck me to hardness first.” She eagerly pushed back from her desk, I dropped my pants and put my cock in my principal’s mouth. She was still masturbating as she sucked me. I was hard very quickly. She stood up, pulled off her skirt and panties, and knelt on the desk, her hips hanging back. I got behind her and pushed into her pussy. She was very, very wet, and she started moaning from the minute I entered her.

“You’re, really, good, at, that”, she gasped between thrusts.

“I’ve had a lot of practice, Deborah.”

“Oh, this is so wrong! I’m fucking a student! Oh, that’s so fucking hot. Oh my God, I’m going to come.”

And she did, wetly, on my cock. I was rock-hard and kept fucking her through two more orgasms.

“Aren’t, you, going, to, come in me?” she asked between gasps.

“Maybe not very quickly. You see, I already fucked my little sister this morning. She’s a sophomore at this school, you might remember.”

“Oh, that’s very naughty!”

“Yes. In fact, I fucked my little sister in the ass, and I came pretty hard in her tight little asshole. So, I might not come again in your pussy so soon.”

“Oh, fuck!” She was coming again. There was actually a little puddle of her woman-cum on the desk under her. “Well, you like anal sex, do you want to finish in my ass?”

“That’s tempting, but shouldn’t we warm you up first, back here?” I wet a finger with her pussy-juice and put it up to her asshole. To my surprise, it went in pretty easily.

“I don’t care. I want to feel you come inside me. Don’t you want it? Don’t you want to fuck your principal in the ass?”

“You are pretty convincing,” I agreed, pulling out and putting the head of my cock up against her sphincter. No matter what she said, some things should not be rushed. I spent a full minute working my cock into her ass, pulled it out a couple times to wet it with her pussy juice, and then went all the way in and started ass-fucking her for real. She grunted and moaned with each thrust.

“You know,” I said, “if you’d called me in here with one of my girlfriends, they’d be eating your pussy right now while I fuck your ass.”

“Oooooh!” she gasped. “I think you’re going to make me come this way.”

“In fact,” I continued, “We could call three girl students in here right now, two to eat your pussy and one to lick my cum out of your asshole after I shoot off into it right now.”

“Oh, fuck!” she cried, then she was coming, a pure anal orgasm fueled by the pictures I put in her head, and then I was coming too, deep inside her.

“Oh my God, thank you,” she said as I helped her down from the desk onto her wobbly legs. She sat down in her chair again. “Well, what are we going to do about that?” She pointed at my half-hard cock. “You can’t go back to class with your cock like that. I should suck it clean.”

“Are you sure?” I looked at my cock. “It doesn’t look dirty, but still ... it was just up your ass.”

“I don’t care.” She pulled me to her and took my half-hard cock all the way into her mouth. She sucked and licked until she was satisfied, then let go of my cock. “Remember, young man. Don’t get distracted from your academics.”

“Yes, ma’am,” I said and I left her office.

With my principal on board, I did end up having a fair bit of sex in school that year. I arranged for a few cute girls to go by the principal’s office to eat her pussy, and sometimes I’d bring a couple guy friends with me and we’d triple-fuck the principal on her desk. She liked her sex rough, and she totally got off on doing it with her students.

One time the school slut, Jasmine, got in trouble in school for saying something too sexual, and was told to report to the principal’s office that afternoon. Well, once I heard about it, I made sure that I showed up with her, and her brother John too. I locked the door behind us as we came into Mrs. Hershel’s office.

“Only the young woman is supposed to report to me,” said the principal sternly.

“Drop it, Deborah.” I said. “You’re a kinky woman, and Jasmine here is the most promiscuous girl in the school. I’m sure we can work something out.”

“I eat pussy,” offered Jasmine, “and my big brother John has a big cock he could fuck you with.”

“Yeah,” said John. He was on the football team. He was a nice guy, but he wasn’t the brightest bulb.

“Jasmine here is such a slut, she even fucks her brother,” I offered helpfully.

“Both my brothers,” corrected Jasmine.

“What will it be, Deborah?” I continued. “You could just cite Jasmine here for a violation of the school policy. Or you could use these two students of yours for whatever twisted sex acts you desire. I’m also happy to help. How about it?”

Deborah nodded. “OK, Fine. You!” She pointed to me. “Come over here and fuck me. I want to watch the little slut commit incest right here in front of me. I’ve never seen that before. You, slut, strip and start sucking your brother’s cock.”

Deborah dropped her skirt and panties and got on her desk, I got behind her to fuck her. Jasmine gleefully threw off her clothes, dropped to her knees, fished John’s cock out of his pants, and started sucking.

“Yes, fuck, that’s hot.” said Deborah. “My students are so nasty. I love it. Take it down your throat, slut. John, grab your sister’s head and fuck her mouth. Yeah, like that. Oh, I love it. OK, now stand her up. Fuck your sister from behind. I want to see your cock going in. Fuck her hard!”

I fucked Deborah hard and rough, the way she liked it. She demanded the same of Jasmine and John, and they did it. Deborah came once on my cock, then Jasmine came (while getting fucked standing up, quite impressive), then John came inside his sister.

It was quite a while by the time the principal was finally through with us. She had John fuck her hard while making Jasmine fist herself, then she wanted to suck Jasmine’s fingers clean of her brother’s spunk. Deborah came on John’s cock, then got off and lay on the desk for Jasmine to eat her pussy, while insisting that John and I take turns fucking Jasmine in the ass, then bringing our cocks to Deborah’s mouth for her to suck them clean while she came on Jasmine’s mouth. Finally, she wanted John and I to double-fuck her while she sucked Jasmine’s pussy (not licking her clit, just drinking her girl juice). Deborah came on our cocks, then we both came in holes, which she roughly forced Jasmine to suck clean of spunk.

When Jasmine was done, Deborah pulled her to her feet and kissed the girl hard, presumably with the taste of ass, pussy and sperm between their mouths. The kiss went on a long time, and when it finally ended they were both smiling. Two kinky sluts had met, and they were friends from that point forward.

By Thanksgiving, Katie’s belly was really big, and her mother’s was not far behind. My family had a regular Thanksgiving dinner at our house, including Scott (as Samantha’s fiancé, he was family) and Lisa and Katie (even my Dad knew I had two pregnant girlfriends). Then we (minus my parents) went over to the Okassian’s house, along with a bunch of other girls I knew including Erin and Janie, to have a different kind of party. It was Katie’s idea - a food sex party. With Thanksgiving leftovers, and a lot of wine. The best ideas we came up with included the pea game (a single green pea in a girl’s pussy, where everyone competes to extract it with their tongue - it’s even funnier when both the pea girl and the licker are drunk), cranberry sauce as a flavoring for clits and nipples, and the kinkiest was Natasha, who was abstaining from the wine because of her pregnancy, but was obvious drunk with lust anyway. She spread her legs wide and invited all the girls to fuck her with a whole turkey drumstick. It was as large as a good-sized fist, slippery with its own juices, and together with some clit-licking Natasha came several times on that drumstick. In the orgy that followed, all the girls remarked on how delicious Natasha’s turkey-flavored pregnant pussy was. Scott and I were kept busy fucking everything in sight, and wrapped up the party with a few DPs on the girls that wanted them, with our loads of cum shared between many mouths.

By Christmas time, there were a lot of very pregnant girls in my life. Katie was at 8 months and enormous. Natasha was at 6 months. Lisa, Erin, Janie, and Margie were all at 5 months. Finally, my sister Samantha was at 4 months with Scott’s baby. Then, there were two 30-something women in the neighborhood, Suzie who was Asian, and Monique who was black, who were both really pregnant, although not by me. Their husbands didn’t know that they snuck over to have sex with me and whatever other females were around. We didn’t actually use my house that often, but Katie and Natasha’s instead. It became a regular thing, a pregnant sex party at that house, every Tuesday night. Usually, all nine pregnant girls and women would make it, and spend a solid three hours having every possible kind of sex with each other, with me, and Scott, and whatever guy friends I brought with me. Once I heard that Lisa’s dad Tom was really turned on by pregnant women, we let him show up too. The only girls we didn’t let him fuck were the youngest - Katie, Erin, and Janie. Everyone was surprised and turned on the first time Tom came over, insisting on watching him do it with his pregnant daughter Lisa (which he did - mouth, pussy, and ass). Tom’s cock was big enough that he could fuck the grown women (Natasha, Margie, Suzie, and Monique) in their pregnant pussies and still give ‘em a good stuffing. Personally, the only girl I usually pussy-fucked at those parties was little Janie. All the rest I ass-fucked, especially while they were getting their pregnant pussies eaten by another girl. There’s just something sexy and special to me about a girl, with swollen belly and sensitive breasts, looking like the epitome of motherhood, spreading her butt-cheeks and encouraging me to sodomize her harder and deeper.

I also love watching pregnant girls carefully 69ing, doing their best to slurp clits and drink pussy juice while keeping their bellies comfortable. And pregnant girls fucking each other with strap-ons. I love that. Even better with the incestuous angle, like Margie and her daughters, or Natasha and Katie. One time we even tried out a double-prong strap-on, and let Katie try fucking her pregnant mom in the pussy and ass at the same time, then turned it around and Natasha double-fucked her pregnant daughter. The impressive thing is that they actually managed to make each other come that way!

I found myself spending a lot of time with Lisa. We went for walks in the snow, I helped her run errands, I carried stuff for her since she was, after all, heavy with my child. I spent many a dinner at her family’s fancy house which didn’t always involve four-way sex with her and her parents (although it often did). Sometimes we just read books or talked about the places we wanted to travel. I realized I was in love with her.

One afternoon, I sat in my room alone, pondering it. I was in love with Lisa. I could see having a future with her. I was also in love with Katie, but in a different way. I was, you could say, “enraptured” by Natasha’s grace and womanly form, but not in love with her. And some part of my heart always belonged to my secret girlfriend, my little sister Sabrina, who was always so sweet to me. I wasn’t in love with Margie or her daughters, even though they also carried my babies.

I pulled my Plot Device out of the locked box and set it on the table. Could it advance my plot in a romantic direction? Could it help me decide what to do? It had only ever introduced sexual plot elements to the story of my life. I put it away. I’d have to advance this part of the story myself.

I made a couple phone calls, and soon had Lisa, Katie, and my sisters in my room. After all the kisses of greeting, we settled down into chair and my bed, the only places to sit.

“All of you, I’ve come to a decision about my life.”

“You have some new crazy sexual plot twist in mind?” asked Samantha. “I don’t think there’s anything you haven’t done sexually with all of us in this room.”

“Not something sexual. Something romantic.”

That got their attention.

“Samantha, I’m so happy you’re marrying Scott. You guys are great and you’ll always be a big part of my life. But I’m realizing that I want to get married too.”

“Oh!” said Lisa. “But ... you can only marry one person, and you have multiple girlfriends.”

“I realize that. So, I’ve come up with a solution. I can only have one wife, legally, visible to the public. But that’s just for the government. I can take as many wives as I want, in private.” I turned to very pregnant Lisa, and got down on my bended knee.

“Lisa, will you marry me?”

“Oh, my sweet Mike, of course I’ll marry you.” She had tears of joy in her eyes.

“Wonderful!” I kissed her. Then I turned to extremely pregnant Katie. “Katie, will you marry me?”

She giggled. “Wow! Yes, of course I’ll marry you.”

I kissed Katie, then looked over at Sabrina. She had a complex expression on her face, happy but sad. I turned to her.

“Sabrina, will you marry me?”

“You can’t...” began Samantha, then she shut up.

Sabrina’s jaw dropped, then slowly turned from amazement to joy. “Yes! Mike, I’ll marry you too!”

“Good!” I opened my arms. Suddenly I had three girls all trying to embrace and kiss me at once. It was fun.

“Now Lisa, if you don’t mind, it will raise the least eyebrows if you’re my legal wife. But in truth, I love all three of you and you will all be completely equally my wives.”

“Yes, no problem.” said Lisa.

“Marrying our little sister, huh?” asked Samantha. “Well, I guess you can.”

“Of course I can. She’s been my secret girlfriend since we started having sex last year. I love her completely and she loves me.”

“I do,” confirmed Sabrina. “I can be my brother’s secret wife!”

“And so what if we can’t have children. Goodness knows there’s going to be enough little Mikes going around. And I actually think that aside from me, Sabrina would prefer girls.” I turned to Sabrina. “Maybe you’ll take Erin or some lucky lady as your wife someday.”

“Yeah. I’d love that.” Sabrina glowed.

I looked at my three fiancés - tall skinny blonde Lisa, short voluptuous dark-haired Katie, and my sweet little sister. “Now, I suggest we all have sex together.”

“I’m horny already,” offered Samantha.

“Good. Come here and deep-throat my cock while my three wives-to-be strip naked and suck each other’s pussies.”

“Oh yeah!” agreed Lisa, and there was a flurry of undressing.

It was a marathon sex session, and I carefully rationed my orgasms, although the girls lost count of theirs. I thoroughly, completely fucked all twelve holes available to me, including the three pussies and three assholes made kinkier by pregnancy. There was ass-to-mouth between each of my fiancés, I came once in Lisa’s mouth and had her share it with the others, came once in Katie’s super-pregnant pussy for the others to slurp it out, and ended with an extra long and vigorous incestuous ass-fuck of my sweet Sabrina.

The wedding was planned, but there was the thorny issue of what to do about Dad. We couldn’t very well plan a wedding without finally letting him in on what was happening in his house. Mom, me, and my sisters got together to have a private talk about it.

“Your Father already suspects a lot,” said Mom. “Even though he works long hours and goes on business trips, he’s still around enough to see a steady stream of so-called girlfriends coming over and going into Mike’s room. And you girls, you go around the house half-dressed too often, he’s already caught sight of you naked many times. It has quite an effect on him. Your father is a very sexual man, that’s part of why he and I are swingers.”

“So, he won’t be very shocked?” I asked hopefully.

“Shocked that you’re fucking half the women in town, no probably not. Fucking your sisters, yeah he’ll be surprised. And marrying one of them. Jesus! Why is it that we’ve kept him in the dark for so long?”

“Because we didn’t know,” said Samantha. “Sabrina and I thought, if he knew we were fucking Mike and having sex with you and lots of other boys and men, he’d want to have sex with us too, and that sounded scary. I mean, way back when.”

“Well that’s not a problem, sweetheart. Your father loves you both and respects your boundaries, if you want to go around naked and have orgies right in front of him, he still won’t lay a finger on you unless you want him to. Respecting boundaries is also something we learn in the swinger world.”

“That’s cool.” Samantha pondered it. “Actually, I’m not so sure it’s scary. It’s kinda sexy to me now, I mean the person I am today.”

“What, having sex with Dad?” asked Sabrina.

“Yeah. I think I could do it. At least, I’d try it.” Samantha smiled. “And I could finally come into your bed, Mom, and do it with both you together.”

“That sounds really sweet and sexy, honey,” encouraged Mom, “if you’re comfortable with it.”

“Well if you’re going to do it, I’m going to do it too,” said Sabrina. “Is it OK with you, Mike?”

I shrugged. “It’s weird to me, but only because you’re my family. I think it’s totally sexy when Lisa fucks her dad. So yeah, go ahead and try it and see how your feel about it.”

“But, will he want to?” asked Samantha. “Maybe he just wants us to be his girls, not his lovers.”

“I think he’ll want to,” laughed Mom, “because it’s been an element of our fantasy life for years. In bed, I’ll have him call me by one of your names and I call him Daddy, and we pretend he’s doing the incest thing. Usually gets him off quick.”

“Wow!” said Samantha. “That’s kinda weird, and kinda exciting too. Let’s do it!”

Mom and the girls chose dinner that night to tell Dad. After dinner was usually a family discussion time.

“The children have something to tell you,” said Mom.

“Yes?” he replied curiously.

“Yeah, Dad,” I began, “Well, you probably know that I’ve been having a lot of sex with a lot of girls in the past year.”

“Yeah, I know.” He beamed at me with pride. “You are quite the man!”

“Yeah, well, I’m doing it with Sam and Sabrina too.”

He nodded and smiled. “Yeah, I know that too.”

“You knew?!” asked Samantha in amazement.

“Hell, yes. You kids aren’t as discreet as you think you are. I know what’s going on under my own roof. I know Mike and you girls have been doing a lot more than just “experimenting” with each other and your friends. I’ve overhead it a few times and it sounds more like balls-to-the-wall sex. And you, little missy!” He pointed to Sabrina and chuckled. “You’ve got a steady stream of little girlfriends coming over to your room, it’s not hard to guess what for. And one time, there was nobody home but you two girls, but the sound of eating pussy was unmistakable, so I know you’re doing each other too. And having a great time, from the sound of it.”

There was a stunned silence around the table for a moment.

“Wow! And Dad, you’re OK with all of it?” asked Samantha.

“Sammie sweetheart, your mother and I are swingers. Of course we’re OK with the sex part. The incest part, I don’t see any harm in it. You obviously know what you’re doing, and avoiding any two-headed babies. I take it that baby you’re carrying is really your fiancés, right Samantha?”

“Of course, Daddy.”

“Well then, you’re grown up and can make your own decisions.”

“Oh, Daddy!” Sam and Sabina got up from the table and ran to embrace Dad, hugging him and kissing his cheeks.

“Um, Daddy,” asked Sabina shyly. “Are you going to want to do it with us now? I mean, sex?”

Dad looked serious. “Well, that’s totally up to you, sweetheart. I’m not interested unless you are.”

“That’s not what Mom told us!” said Sam. “She said you do role-playing with her pretending to fuck us.”

“OK. Guilty as charge. But that’s just fantasy. I can remain your non-sexual Dad if you want.”

“Nope.” Samantha smiled big. “I used to be scared, but I am totally ready now. Take me to bed and let’s do it.”

“Me too!” said Sabrina, then she turned to me. “Is it OK, Mike?” I knew why she was asking. She was my secret girlfriend, and she was asking me to share her with another man.

“Totally OK,” I said. “Enjoy it, Dad. They’re awesome at sex.”

“Can we do it NOW?” asked Samantha.

“Sure, honey.” Dad got up from the table.

“Knock yourselves out. I’ve got homework to do,” I said, going to my room.

Less than an hour later, my sisters came to my room. They were naked and flushed with sexual glow.

“Mikey!” they giggled, trying to pull my attention away from my homework.

“Yes? Well, how did it go?” I asked.

“It was great!” Sam smiled big. “Mom and me masturbated each other while we watched Dad and Sabrina get all naked and make out with each other. Then I got my turn with Dad. Then Sabrina and I sucked his cock together. He barely lasted a minute, he was so excited! We had to suck him some more to get him hard again, and then he wanted to watch us eating Mom’s pussy, and Mom eating our pussies, and then finally he was read to fuck. He put us right on top of each other and fucked us like that, back and forth between our pussies as he kissed Mom. His cock’s pretty big.” She giggled. “And he came inside both of us.”