Chapter 17: Tight fit

October 13, 2001, Chicago, Illinois

🎤 Steve

“This,” Hope said, holding up her hand, “is my purity ring. Will you take it off?”

“Yes,” I replied with no hesitation.

“Do you want to know why I waited to ask?”

“If you want to tell me.”

“I told you I read the book, right? Well, the advice was to go on the Pill. I got my prescription once I arrived in Chicago and had to wait a month after my last period.”

“Wise, though I had a vasectomy, so in this specific instance, you didn’t need to do that.”

“Doctor Bethany was adamant that a girl never assume anything with regard to birth control, and I didn’t think it was right to discuss it before I asked you to remove my ring. She was also adamant about STI tests. I’m supposed to ask you if you had one; I did.”

I was impressed that Hope had read the material and taken it to heart. And I was pleased with Sandy ensuring Hope had a proper education, despite Hope’s adoptive parents doing their level best to prevent it.

“I suppose this is where I show you mine and you show me yours.”

“Here?” Hope smirked. “I figured the first time would be in a bedroom!”

Which actually presented a logistical problem I hadn’t thought about before Hope mentioned a bedroom - there wasn’t one available. All the upstairs bedrooms were spoken for by my family, including Suzanne. The former nanny room was being used by Natalie for her weekend stays with us, Leigh was using one of the guest bedrooms as she did on weekends, and Matthew was in the other guest bedroom, and had decided to stay until Sunday dinner.

“I meant our test results!” I declared mirthfully.

I went to the small table where I kept my wallet and keys and extracted my card, which I’d actually need to update by the end of the month, and showed it to Hope. She opened her purse and extracted a folded sheet of paper which she handed to me. We each verified the results, then returned the documents.

“Birth control? Check! STI test? Check! Handsome man with whom I want to ‘fit together’? Check! Consent? Check! The only thing left on Doctor Bethany’s checklist is a private place where we can take our time so I have a wonderful first experience.”

“That’s actually a minor obstacle - because my son Matthew is here for the weekend, we’re short on available bedrooms.”

Hope smiled, “Natalie is leaving in about twenty minutes. She won’t be home until after midnight and said it was OK to use her room.”

“Advance planning?” I asked.

“She knew I was going to ask you, and told me last month we could use her room. I checked with her while you were at karate to make sure.”

“There’s another option, if it interests you, though I’d have to double-check that it was OK.”

“What’s that?”

“My company leases an apartment in the West Loop. If we went there, we could order food and be totally alone and not interrupted. And I wouldn’t have to be back here before 1:00pm tomorrow.”

“I love that idea, and wonder if we can split the difference?”

“How so?”

“Natalie’s room has a mirror on the ceiling! I could watch while you expertly deflower me, and then we could spend the night in that apartment.”

Hope’s assertiveness made it clear that her delay was for exactly the reason she’d expressed - waiting for her birth control pills to take effect. And that meant her decision had been made more than a month ago. And that made me curious.

“I just need to check with my wives that it’s OK to spend the night at the apartment, but I have one question, if I may.”

“Sure.”

“When did you decide?”

“After my first visit here in the Spring. I know we only spoke for a few minutes, but with everything my birth mom had told me about you, something just clicked. It was like a switch flipped in my brain. When I went home, I talked to my birth mom and that’s when she ‘warned’ me that if I asked you to mentor me I wouldn’t be a virgin by Christmastime. That was already what I wanted, so that actually made me happy, because I knew it might really happen.

“And I told you why - it started with curiosity, and once I had met you, there was attraction and desire. And honestly, that’s enough, but it also is sort of a declaration of independence, which Doctor Bethany called a ‘traditional rite of passage’. What I said that day when you asked me, was that going to bed together, fucking, was necessary to remove the shackles my adoptive parents put on me. And, unless you tell me not to, I’m going to write a letter to my grandfather telling him that I asked you to deflower me, and that it was glorious, which I’m sure it will be.

“Then, on top of all of that, the absolute taboos that I’d be violating - having sex with a married man and having that married man, who deflowered my mom, deflower me. I know that might sound like a strange desire, but I think it’s all bound up in the straitjacket the church put on me. Ever since I decided I wanted to go to bed with you, I’ve had this odd fantasy of walking into my grandfather’s church and announcing I’m no longer a virgin the way Ariel did in Footloose, though my fantasy had the church full of congregants.

“And, before you ask your next question - what happens after tonight? That’s pretty simple - you help me become the woman I’m meant to be. Mentor me, challenge me, and, eventually, hire me. Include me in your Philosophy Club. And, assuming the sex is good, which I expect it to be, go to bed with me in the future.

“As for today and tonight - when you take off this ring, all inhibitions are cast aside. I’ll have a completely open mind and offer a completely open body. I’m willing to do anything in the ‘How we fit together’ chapter of the book, and want you to teach me how to give, and receive, ultimate pleasure. I also understand that this might be the one and only time we’re together, and if that happens, nothing else about what I want from you changes.”

She had certainly thought things through, and there wasn’t a bit of hesitation, nor had there been a bit of pushback against my mentoring methods. Actually, not only had she not pushed back, but she’d embraced it as tightly as we were about to embrace. And THAT thought, brought about the realization that Hope was, in many ways, a perfect candidate for the Inner Circle. She and Suzanne had similar qualities, though coming from very different upbringings and experiences. I was reticent to expand the Inner Circle, but Hope was such a perfect candidate that I’d need to speak to Suzanne about it. Of course, an offer like that carried with it a significant commitment that Hope might not be ready to make, and, which might not be in her best interests.

“Then all that’s left to do is have a word with my wives.”

“Do you need permission in general? Or just to stay out all night?”

“My agreement with my wives is that I manage my own sex life, with the caveat that I follow our agreed-upon rules, which include them knowing about all of my relationships. One of the rules is that I need to ask about overnight stays, if it would be a night I’d normally sleep with my wives.”

“I’d like to know all the rules, if you don’t mind.”

“Let me quickly check with Kara and Jessica so I know how much time we have. Then we can talk or get right to the activity you requested earlier.”

“I’ll see if Natalie and Leigh have left yet, and make sure Natalie doesn’t need anything from her room.”

We both left my study and I found my wives in the sunroom.

“Hope asked me to remove her purity ring,” I said.

“It was only a matter of time,” Kara smirked.

“Unless either of you objects, I’d like to spend the night with her. We’d go to the apartment because all of the rooms here are occupied.”

“I don’t have a problem, Jess,” Kara said. “Do you?”

“No. And Jennifer and Josie asked if we wanted to go out, so we’ll have something to do this evening. The kids all have plans, too. What about dinner?”

“We’ll probably order when we’re at the apartment.”

“When will you leave?” Jessica asked.

I chuckled, “After we take Natalie up on the offer she made to Hope. Something to do with mirrors on the ceiling.”

My wives both laughed.

“Now, if we just change it out for one-way glass, and install a video camera...” Kara teased.

“You and your voyeuristic desires,” I chuckled.

“Now, if that situation with the cheer team happened, THAT would be something to watch!” Kara exclaimed, her voice dripping with desire.

I chuckled, “As if the fantasy of a dozen or so virgin, bi-curious cheerleaders isn’t enough, you want them also to agree to let you watch?”

“Don’t you think they’d agree? I mean, if the entire team watches...”

“You are SO bad, Kara!” Jessica teased.

“And YOU didn’t get off watching Tiger deflower Suzanne?”

“Maybe,” Jessica allowed.

“Go have your fun, Snuggle Bear.”

“Thanks. I love you both!”

“We love you, too!” Kara and Jessica declared in unison.

I kissed each of them, then left the sunroom to find Hope standing just outside the door to my study.

“All set,” she said. “Natalie got her purse and won’t need to come back to her room.”

I took Hope’s hand and led her to the nanny room, locking the door to the kitchen, giving us complete privacy, as well as access to a shower. We went into the bedroom where I turned on the stereo and tuned to the jazz station I liked, then turned to face Hope.

“Before we get to the ‘planned activity’, would you tell me the rules?”

I felt I could safely leave out ‘Rule 0’ as it was meant to address a specific concern which Jessica had expressed, and was absolutely inviolable because of what had happened with my sister.

“First,” I said, “no sex with anyone in a committed relationship. Second, no sex with girls under the age of consent. Third, no sex with employees or customers of my company, nor employees of the hospital where Jess works, nor of UofC’s science department, which is where Kara works, nor any students of the dojo. There can be case-by-case exceptions to the rules, for example, Suzanne and Leigh, but those exceptions are few and far between, and need express permission, in advance, from my wives.”

“What’s with the restriction on committed relationships? You’re married!”

“Yes, and the freedom to have other sex partners was part of our agreement before we married. Kara and Jessica have the same freedom, but they’ve elected not to use it. The rule is in place because while I know exactly what the situation is in my relationship, I can’t be sure what it is in someone else’s. I won’t be a party to cheating, and it’s very, very difficult to discern if that’s happening. If I’m positive the other person isn’t violating their commitments, then it becomes a possibility.”

“I hadn’t considered that. You obviously have permission, and everyone knows it, but I can see how you might not be sure about someone else.”

“I actually have freedom, not permission. My wives and I agree that the decision when, and with whom, to have sex, is a very personal decision, and nobody should be able to tell you when you can have sex or with whom you can do it. You can voluntarily give up that freedom, if you choose, but it is always yours. Some people object to fornication; some to adultery. But nobody should determine those things for anyone else, except in the context of their own relationship.”

“Do you believe there is such a thing as sin?”

“As it’s usually meant? No. To me, a sin would be something that harmed another person or which violated my own principles or me breaking my word, but only in the sense of falling short. And, that’s actually the Biblical view of sin - falling short of perfection. And when you do, you figure out how and why you fell short, resolve to do better, and move on with your life. That’s not far from the Eastern Orthodox view on sin. May I ask a question?”

“Of course!”

“Do you consider yourself a Christian?”

“I think the best answer right now is that I don’t know.”

“That is, in my mind, not only the best answer, but the only possible answer.”

“Thanks for answering my questions.”

“You’re welcome.”

“Undress me, please,” Hope requested. “The ring first.”

Hope held out her left hand I stepped forward, taking her hand in my left, and using my right hand to gently pull the purity ring from her finger. I wasn’t sure what to do with it, so I put it in my pants pocket, then began undressing her. Starting with her blouse, I carefully removed each piece of clothing, revealing, in turn, a flat, toned stomach, small, firm breasts, shapely muscular legs, a triangle of downy blonde pubic hair, and glistening, plump labia.

“You’re beautiful!” I declared, looking directly into her gorgeous blue eyes.

“Thanks. And besides my doctor, you’re the first person to see me this way.”

“Thank you.”

Hope laughed, “You’ll get all the other firsts, too, so you can save the ‘thank you’ for tomorrow!”

I chuckled, “I love your sense of humor!”

“Thanks,” she smirked. “I’d like to undress you, please.”

I nodded and Hope began undressing me, revealing, in turn, a toned, but not muscular abdomen, strong, muscular legs, and an erection, which was, according to my female lovers who were doctors, and Bethany’s book, somewhat larger than average, something first declared by Melanie Spencer some twenty-two years previous.

“Wow!” Hope breathed, staring not at my eyes, but at my erection.

“What now?” I asked.

“Now we get into bed and you take me, powerfully, then we go to the apartment you mentioned and you teach me everything else.”

I nodded, stepped forward and to the side, scooped Hope into my arms, and then laid her on the bed. I climbed into bed and carefully laid down on top of her. Hope spread her legs, allowing me to settle between them.

“Good view?” I asked.

Hope laughed softly, “Yes! You have a sexy butt!”

“Thanks.”

“I want to see you put it in, if that’s possible,” Hope requested, her voice dripping with desire.

I nodded, moved to a kneeling position as we used in karate, then lifted Hope’s butt and positioned her legs on either side of mine, her knees bent, such that my glans was position against Hope’s labia.

“Powerfully?” I asked.

“Powerfully,” Hope confirmed.

I nodded, rubbed my glans against her glistening labia to coat it with her juices, then put my hands on her waist, and pulled her firmly toward me as I rose up and thrust forward. My glans parted her labia and pierced a thin ring of flesh. Hope grunted but didn’t protest, so I continued pulling her to me and pushing my hips forward, fully embedding myself in her tight, silky folds.

“Wow!” she gasped. “Take me, Steve! Take me!”

I lowered myself onto her, stretching out my legs. I slipped my hands under her butt to gain leverage, then pulled back and thrust forward once again. Hope grunted and I felt her calves on my thighs as I pulled back once more. Hope groaned and met my next thrust, and I began doing as she requested - powerfully taking her as she met each thrust by raising her hips. It didn’t take long before she gasped and shuddered as a powerful orgasm crashed over her.

“Keep ... going...” she gasped as her tight tunnel became even tighter as it spasmed around my shaft.

I needed no encouragement, and continued my firm, powerful strokes as Hope came down from the pinnacle and began climbing towards the next. Two more peaks followed, before I allowed my own pleasure to build without trying to hold back, and when Hope had her fourth orgasm, I pushed deep into her and ground against her clit as I blasted her spasming pussy full of cum.

When my orgasm passed, I gently pulled out, slid down, and latched onto Hope’s clit. She moaned loudly, begged me to keep going, and I brought her off for a fifth time, feasting on her tangy juices, before moving up next to her, and lying on my back.

“Wow,” she gasped, trying to regain her breath.

“Yeah,” I replied, looking up to see our bodies in the mirror.

Hopes legs were splayed, giving me a wonderful view of her no-longer virgin pussy. As I gazed, I noticed the slightest hint of pink fluid on the inside of Hope’s thighs. Hope, too, was looking in the mirror, which in addition to her gorgeous body, showed mine, my slowly softening shaft also showing hints of her virginal blood. We lay quiet for several minutes before Hope spoke.

“I just realized something!” she said with a soft laugh. “I had sex before you, or anyone else, kissed me! Well, you kissed me between my legs, but never kissed my lips!”

“I can remedy that now, if you’d like.”

It was a few seconds before Hope responded.

“I want to give you a blowjob first,” she said. “Then kiss. Reverse order!”

I suppressed a laugh - first intercourse, first oral sex both ways, THEN first kiss.

“Do you want me to wash my face first?” I asked.

“No, because you’re going to kiss me afterwards!”

Bethany had actually written about the topic in her book, making the point that despite the taboos, it was a wonderful way to express your appreciation for your partner pleasuring you in that way, and a sign of openness and trust.

“Then by all means!” I declared.

“I read the book, but I think you need to guide me.”

“Believe it or not, Bethany’s explanation is pretty much it - treat it like an ice cream cone to start, then a popsicle, use one hand to stroke, and the other to gently cup my testicles. Suck and run your tongue around me and right before I cum, just keep my glans in your mouth, swirl your tongue, suck harder, and stroke harder.”