The Jenna Arrangement Pt. 08

She stroked quickly, twisting her wrist over the head on the upstroke, and within moments I felt myself approaching the point of no return.

My cock swelled in her hand, exploding hot rivulets of cum over her stomach, thighs and panties. My fists clenched behind her back as every muscle in my body tensed and shook with enjoyment.

As my lustful growls subsided, Jenna leaned in, kissing me intensely. She kept stroking me, her speed slowing but continuing to milk every drop from my still pulsing cock.

Her emerald eyes were on fire with lust. "I need one more," she pleaded, "just one more, it's so close..."

Her hand returned to her panties, slipping inside. Her forehead was against mine, eye to eye, our noses almost touching, as she furiously rubbed her clit.

I put my hand over hers, not touching her pussy, no, but feeling her hand inside her panties as she worked herself towards another climax.

Even with our faces so close, I could see Jenna smile. Then her eyes closed, her lips trembled, and I felt her tense yet again. "Cum for me, princess," I whispered.

She came in soft moans, her body shaking over me until she finally collapsed against my chest. She rested her head on my shoulder, the heavy panting of her breath slowly subsiding.

I wrapped my arms around her, and we held each other for a brief eternity.

-------------------------------------------------------

"Can I ask you something?" Jenna sounded hesitant.

I looked up from tying my shoes. Jenna hadn't asked me to spend the night, and I wasn't going to push it. "Of course, darlin', anything you want."

"Your little...fantasy. You know, the one that brought us together. I'm curious how that started, what it does for you, if you've done things like that before."

I sat back on the couch, collecting my thoughts, trying to decide where to begin. Jenna sat beside me, fully dressed now as well. "Unless it feels like I'm prying, or you don't want to talk about it," she offered.

"No, it's okay. I don't mind. I guess it started during the latter years of my marriage. Things weren't going well, and sex was...well, practically non-existent." I skipped over the details about how my wife had found religion, and how the more she'd accepted Jesus, the less she'd accepted me, or my atheism. Jenna and I had never discussed religion, and I hoped it wouldn't become an issue for us down the road. I had no problems with people of faith, just those who took it to extremes.

"I did my best to be patient, and occasionally tried to spice things up. I once intentionally set things up so she'd catch me masturbating, hoping it might spark something, maybe get her to participate. She called me a filthy pig and stormed out of the bedroom.

"She caught me watching porn another night, accidentally that time, and threatened to divorce me right then and there. I kept my masturbatory habits to myself after that."

Jenna took my hand, holding it compassionately, as I continued.

"In the final years, I was exploring other outlets for my sexual needs, mostly online. Chat rooms were just becoming a thing then, and there were lots of women, or at least I hoped they were women, willing to have virtual fantasies with me.

"As webcams became more popular, it was even easier, and I had several women I'd made friends with that liked to play.

"One young lady in particular, she was about your age I guess, I'd struck up a friendship with that started out strictly non-sexual. Then one night a group of us were all chatting together, one thing led to another, and eventually I wound up masturbating for her in a private session. She remained clothed the entire time, much like you when you told me about your adventures on Omegle.

"That planted the seed, I suppose. There was something, I dunno, appealing about it. The idea of doing something normally considered taboo, something you usually kept private, doing it in front of someone and they simply...watched you. No strings, no expectations.

"It's an interesting fantasy I suppose. In a way it's very one-sided, and that's part of the appeal. The guy gets to be open and free and express himself sexually, while the woman is under no obligation to please him, nor he to please her, really. But it's also about the connection, and trust; about being with someone in that way who truly knows and understands and isn't judging you for it. Maybe they think you're sexy, or maybe they just care enough about you to be open to letting you express yourself that way. Does that make any sense at all?"

Jenna nodded. "I think I get it. It's about being able to express yourself sexually, to share that part of yourself without fear, but also without pressure."

"Exactly," I said. "It's this strange combination of self expression and intimacy. And it's very hard to create that experience in real life. You can't just ask the woman next door or your co-worker or even your best female friend if you can get naked or jack off in front of her.

"There were certain Adult Clubs I could go to that had private booths, girls behind the glass, and I could pay to look at them and jerk off. That satisfied me for a while, but quickly got tiresome. And expensive. Some girls were better at feigning interest than others, but in the end it was always about the money; pay them, get off, and go."

I paused at this point, deciding how much I wanted to reveal, but decided I needed to be truthful in everything with Jenna.

"I was, eventually, unfaithful to my wife. I'm not proud of that. And it hurt her, which I deeply regret, no matter our issues.

"When she discovered my affair, that pretty much sealed the deal. We divorced quickly and without much fuss."

"I'm sorry," Jenna said softly. "That must have been hard on you."

I nodded gratefully. "I went through a few other relationships after that, none of them lasting very long. The last one, we'd been seeing each other for over a year. She dumped me in a Facebook message, can you imagine that? Said an 'old friend' had come back into her life and she'd decided to explore things with him. Never heard from her again, never returned my calls or messages.

"Anyway, I decided to stay single for a while after that. I figured maybe I just wasn't cut out for long term relationships, that I must be doing something wrong.

But a man still has needs. So I went to strip clubs and the occasional massage parlors. Even hired a few 'escorts' I found online from time to time. I hope you don't think poorly of me for that."

Jenna shook her head. "No, of course not. I don't think there's anything shameful about sex workers, nor in men who use them. Although I'm not thrilled about the less savory aspects like sex trafficking and forced prostitution."

"Of course, absolutely," I said, "and I stopped going to massage parlors after a while because of the probability of that kind of thing.

"Plus, overall, paying for sex, while serving a purpose, is ultimately unsatisfying for me. I would always wind up thinking of my wife, who in the last several years would only have sex with me if I complained about it enough, just to shut me up. And how unfulfilling it was to have sex with a woman who wasn't actually into it, into ME.

Prostitutes can be very talented, and many of them are great actresses, but deep down I knew. Sure, they'd fuck me. Maybe they even got off too. But it wasn't ME they really wanted. Just my wallet."

Jenna looked sadly thoughtful. "I...I get that. My past boyfriends. I got the feeling they just wanted me for sex. Didn't love me, or even really care about me. Just...my body."

I nodded in agreement. "Opposite ends of the same thing, I suppose."

Silence hung over the room for a few moments. Then Jenna asked gingerly, "What...what really made you place that ad?"

I sighed, contemplating my answer.

"Boredom. Loneliness. Frustration I guess. I was looking for something...different. A way to cut through all the bullshit. I could have just hired a prostitute, sure, and she would have oh'd and ah'd and gushed over how 'hot' I was and how big my dick was and probably flashed or teased or even stripped for me, then take my money and hustle out the door as soon as our time was up.

"I guess I was just hoping for something new. A way I could just be me, and whoever answered the ad could just be themselves too."

Jenna gripped my hand tighter and smiled up at me. "Well I guess that's exactly what you found, then, huh?"

As I looked into her caring, sincere and loving face, I suddenly felt myself on the verge of tears. "I sure did, darlin'." I pulled her into me, hugging her tightly. "Thank you. Thank you for that."

Jenna held me tight as I wept on her shoulder. "You're welcome," she said, stroking my hair. "You're very welcome."

-------------------------------------------------------

Authors Afterwards:

It seems Jenna and Tom have finally bonded, not just physically, but emotionally as well. I could probably end their tale right here.

But there's still more to tell.

For those readers who prefer the CFNM elements, fear not. Jenna and Tom will continue to explore this fetish together as their relationship grows. They've established trust and communication, two important elements to CFNM as well as relationships in general. They may even reverse the roles and explore CMNF as well. I also have plans for them to explore more extreme versions of voyeurism and exhibitionism. But they need to build up to these things at their own pace.

I still have at least several more adventures outlined in my mind if not yet in print.

To be continued, of course.