Walking BJ

Takes place immediately after Walking BJ: The Late Night

___

Jules answered her door and I heard her ask, "Who are you?"

The reply I heard was, "Is Mr. Schuster here? I really need him."

This can't be good. Well, I guess I know where I'm starting...

I had just gotten to Jules' house and was about to fill her in on all that had gone on that I hadn't been able to tell her about. How I had found out our peeping Tom was Cindy, who is now standing in front of her. How I was manipulated into being Cindy's sexual mentor. How I found out my wife, Carol, was having an affair with Cindy's mom. And finally, how Carol knows about Jules and I, and now wants to share our partners.

Jules replied, "He might be, but again, who are you? And why are you at my back door?"

"Mrs. Martinez, it's me, Cindy. Selina's old friend. I saw Mr. Schuster come in this way so I followed."

Man, Cindy was good at tailing me. I hadn't seen her when I had checked behind me.

Jules nodded, "Oh, yeah. I remember you. We walked by you in the park a couple of months back."

Jules reluctantly stepped aside to allow Cindy entry. Cindy came in the room glancing around looking for me. When she saw me on the couch, she rushed over and knelt on the floor at my feet.

"Mr. Schuster. I need your help again, and it needs to be tonight."

Clearly stunned, Jules asked, "Greg, what the hell is she talking about? And why is she here?"

Before I could answer, Cindy replied with, "Has he not told you? After I had watched you two together, I came to Mr. Schuster for help with my sexual education."

Jules' eyes locked on mine and I stammered with, "I... uh... was about to tell you."

"Rule five Greg! How long has this been going on?"

"It was one time when you were in San Antonio."

"Don't forgot what I did to you when we watched Mrs. Schuster with my mom."

Jules' eyes widened and her jaw dropped before responding with, "What the fuck Greg? I wasn't enough for you on the side? You needed to go after my daughter's friend as well?"

I didn't know how to respond. I was literally about to tell her, and knew I should have sooner, but I couldn't have imagined it would come out like this.

"In his defense Mrs. Martinez, I did kind of blackmail him into it, and I was friends with his daughter, Marcia, since we were kids."

"I don't know that that helps Cindy. Maybe makes it a little creepier."

I finally was able to get some words out.

"I was about to tell you tonight. This is what I was going to catch you up on. Yes, Cindy was our peeping Tom and she approached me after we saw her that day. We were together one time..."

"Two, Mr. Schuster."

"Okay, yes, twice when she gave me a hand job while I watched my wife have an affair with her mom. This isn't exactly how I planned to tell you."

I obviously left out how Carol wanted to share Cindy's mom with me. That would have to come out later, if I still got the chance.

Jules paced around the room. There was a moment of silence before she continued, almost speaking to herself.

"Fucking hell Greg..."

She paced some more. It seemed like she was contemplating the situation. Cindy and I just watched.

"So Cindy... What help did you need from Mr. Schuster tonight?"

I took note of the use of my formal name.

"Oh, yeah. I need him to take my virginity."

It was good that I hadn't drank any of my water yet as I would have spat it across the room. The way she was so nonchalant in her request. I was stunned, but Jules just smiled.

"I like her Greg. She's quick and to the point. Knows what she wants. But Cindy, why does it have to be Mr. Schuster?"

"Because he's my teacher. The one I feel safest with. The boy I've been seeing at school doesn't know I'm a virgin, and he's made it pretty clear he expects to have sex when I get back to school this week. I head back tomorrow, so that's why it has to be tonight."

"First of all Cindy, break up with that boy. There shouldn't be any expectations placed on you for that."

"But Mrs. Martinez..."

Jules stopped her with, "Greg. Why don't you go upstairs so we can have some girl talk. You can wait in the spare bedroom up the stairs to the right, first door on the left."

I didn't say anything. I stood and Cindy looked at me with a face that seemed unsure of what was about to happen, like she might be in trouble. She took my place on the couch.

As I passed Jules, she looked at me smirking and slightly shaking her head. After passing her, I kept going and didn't look back.

I found the stairs and went up. There weren't any lights on, so it was dark and I didn't bother looking for any switches. I was able to make out the path provided in the dim light.

I went into the room and found a queen size bed with tucked bedding. There was a dresser and some clothing in a pile on the floor against the wall. Otherwise, it was bare. I wondered if this was the room Jules had been using when Miguel was here.

I sat on the bed wondering how long this would take. I left the bedroom door open, but couldn't hear anything downstairs.

I assumed Jules would talk Cindy out of the silly notion that I needed to take her virginity. How she should wait for the right person. The usual lesson you gave a young woman of her age.

I wondered what would happen now with Jules. I already felt uncomfortable with having not told her about Cindy, but now it felt like I was being outright untruthful and withholding it. She had made her rules pretty clear, and I hadn't followed the one about being completely open and honest.

After a while, I eventually laid down on the bed and thought about the various encounters I'd had with Jules starting with the fateful question of "How's your sex life?" At the time, it wasn't great. I had felt middle aged and unwanted. Carol didn't have much interest in sex, or at least with me, and Jules offered to fill that gap. Since then it has been quite a roller coaster of ups and downs. Right now felt like waiting for the next drop.

As I was in the middle of my thoughts, the hall lit up. I heard some footsteps come up the stairs. I had a hard time telling if it was coming from one pair of feet or two. Jules appeared at the door and came in. I sat up and she sat next to me on the bed.

I started with, "I'm sorry."

"Greg, am I going to have to tattoo our rules on you? No apologies."

She rested her hand on my knee and squeezed.

"I assume you talked her out of it?"

"Um, no, actually. She's in the bathroom getting ready."

"What!? Why?"

"Because we spoke, and I think she needs this to move on. Since you decided to be her sexual mentor, she's fixated on it being you."

"But what about waiting for the right person?"

"Fuck off Greg. Who's the right person? Most of the time it just happens, and if you're lucky enough to have a say in it, you don't end up with that person anyway. She's right. You're safe and will treat her right. She's also a consenting adult, so all good."

"Matches Mal..."

"No. No, Greg. No safe word on this one. You broke rule five. I'm breaking rule two. Besides, the rules don't apply with her. You better get ready. She going to come in in a few. You better make this nice for her."

Jules patted my knee and left the room, partially closing the door on her way out.

I sat for a moment thinking to myself before getting up to undress. I mentally tried to prepare myself for what was about to happen. I had mixed emotions. I was about to have sex with someone my daughter's age, but we had been together already so I was familiar with her and had liked it. I thought about what a lucky guy I was to have her choose me, but what story she'd later tell about who her first was. I'd likely be seen as the creepy older man. Oh, well.

After I finished undressing, I pulled open the sheets and slipped into the bed just as Cindy showed up in the doorway. I could only make out her silhouette. She was naked, and her shape was young and fit. It was the ideal female figure I'd jerk off to in my teenage years letting my imagination run wild with what it would truly look or feel like in person.

Cindy approached the bed and slipped under the covers next to me. She was on her side so we faced each other.

"Thank you for doing this Mr. Schuster."

I didn't have heart to tell her I was a reluctant participant.

"Sure Cindy. Do you know how this works?"

I mean I knew she'd know how it works, but didn't know if she knew what to expect for her first time.

She gave a little giggle and replied, "Yes, Mr. Schuster. I know how this works. We came close enough last time, remember?"

I smiled, "Yes, but I mean for your first time."

"Oh, Mrs. Martinez said there would likely be some pain and a little bleeding. Is that going to bother you?"

"No. That will be fine. I just wanted to make sure you knew what to expect and that it would be normal."

She bit her bottom lip and replied with "Mhmm."

Her eyes looked into mine with a yearning I could just make out with the light that entered the room from the hall. I realized the door was still open.

"Do you want me to close the door?" I asked.

Cindy quickly glanced over at it before turning back to me and replied, "No, I don't mind it being open. I'll be able to better see you in the light and Mrs. Martinez can always peek in to check on us. It's only fair since I've watched you two."

This thought brought out an arousal in my cock, which Cindy found as she reached for it.

"I see you're ready for me Mr. Schuster." she said with a smile and came in for a kiss.

Our lips met and parted. As our tongues tangled, I reach my hand over to touch her body. It felt amazing. I glided my hand up her back to her shoulder blade and back down over her firm ass and down part of her thigh. On my way back up, I gave her ass cheek a squeeze, which elicited a giggle from her through our kissing.

As Cindy stroked me, I played with her firm, perky breasts. They made quite the handful and her nipples were hard as rocks. After a few moments of this, I reached down between her legs. She opened them wide for me and I felt her landing strip of pubic hair before getting to her lean wet pussy. She gave a gasp followed by a moan as I ran my fingers over her lips to her opening. She was soaked so I figured it was time to move on.

I leaned myself into Cindy to move her into position on her back. We broke our kiss and I climbed on top. I held myself up with my hands on the bed as I looked down into her eyes. My cock was currently pressed against her mound.

"Are you ready?" I asked.

Keeping eye contact, she replied, "Yes, Mr. Schuster."

I lowered my upper body to rest on my elbows bringing my hands underneath her. With my chest now pressed against her breasts, our eyes remained locked. I lowered my torso to free my cock and started for her opening.

I felt the tip meet her tight lips. She gave a quick inhale at the anticipation of what was to come. I started to push myself inside. My head breached what had to be the tightest pussy I'd ever entered. I continued entry until my cock was about a third of the way in to give her a moment to adjust.

Cindy gave an exhale with my insertion and I felt her hands grip the back of my upper arms.

"Are you okay?" I asked.

Still looking at me, she nodded and said, "Yes. It feels so full, but doesn't hurt at all."

"I don't think we're there yet."

"What do you mean?"

I pushed myself slowly in some more until I found it, and she winced.

"That's the part that will hurt, once that breaks."

"Okay, Mr. Schuster. I'm ready."

"We are going to take this slow, and it should happen naturally."

Cindy nodded again in acknowledgment and I went in to kiss her. As we kissed, I slowly slid my cock in and out within the distance I'd measured to her hymen. She responded with quickened breathing and subtle moans.

As I continued, my arousal was picking up with Cindy's tight cavity engulfing the upper part of my cock. My pace picked up and for a brief moment I forgot about the barrier and broke through.

She broke our kiss with, "Ouch! Was that it?"

"Yes, sorry. I got carried away. Are you okay?"

"Yeah, it hurts a bit, but this is amazing. Please keep going Mr. Schuster. Let me feel you all the way in now."

"Um, Cindy. I don't know how long I will last. Where do you want me to come?"

"I'm here for the full experience Mr. Schuster. I want you to come inside. Mrs. Martinez told me it would be okay."

And with that, I gave her pussy my full length. I could feel my balls against her ass. She smiled back at me in response.

I got back up on my hands and started thrusting into Cindy at a normal pace now. She spread her legs wide in response, even holding them up with her hands at times. I watched her breasts move up and down her chest to the movement.

I was getting close and and my grunts started to match her moans. Her hands went to my lower back, just above my ass as I started to drive my cock into her harder.

Through her heavy breathing, Cindy panted, "Come on Mr. Schuster. Shoot your load into me."

I remembered she enjoyed that phrase I had used before, and I did. My cock started pumping its load right into her. I could feel my seed exit through my opening with rope after rope. Cindy's tight pussy did an amazing job milking me dry.

As this happened, Cindy exclaimed, "Oh my god! I can feel it throbbing inside! I feel your warmth filling me."

I smiled at her enthusiasm as I started to slow myself down. Before I could exit her, Cindy wrapped her legs around me to keep me inside. It didn't take long for me to soften enough to still slip out.

"Sorry, I wanted to see if I could feel that too." she explained.

I chuckled and brought myself down to lay next to her.

"So how was it?" I asked.

"I couldn't have asked for a better teacher. That was amazing. I have to ask though...Was I supposed to have orgasmed?"

Trying not to feel a little defeated, I replied with, "Well, from my experience, women very rarely orgasm from penetration alone."

"Then how's it supposed to happen during sex?"

"Either you or your partner will need to give you clitoral stimulation."

Cindy's eyes lit up a bit.

"Oh, that makes sense. Seems a bit unfair, but I get it."

I chuckled again at her sense of curiosity and openness to discuss and learn.

"Would you like me to help you orgasm?" I offered.

"Maybe in a moment Mr. Schuster. Let me get started."

At that, she tossed what sheets had been over her to the side exposing her full naked body in the light from the hall. I took in the beauty of it with the highlights and shadows cast on her skin by all of her curves.

Cindy brought her knees up and spread her legs. Her right hand went to her pussy and I could hear her fingers play with the wetness a bit before raising her hand into the light to see the glistening mix of our fluids on her fingers.

Her hand went back down to go to work. Her left hand went to her breast and she started to squeeze it while simultaneously pinching her nipple.

My cock was inching back to life and I reached down to touch it. It was slick and still a little soft, but hardened more as I started to run my fingers over it.

Cindy's eyes were closed. I watched her pleasure herself as I started stroking my cock. I could hear her fingers plunging into her thick wetness. I wondered if she was thinking about what we had just done. I know I was and was about ready to do it again.

Before I could take any action on my thought, she asked, "Mr. Schuster. Have you recovered yet?"

"Yes, Cindy. I'm stroking it right now."

She opened her eyes and turned her head to watch me stroke my slick length as she played with herself.

"Good. Now lay on your back."

I took notice of her command and followed her direction. I laid back and pointed my cock straight up as I continued to make myself ready.

Cindy then got up and moved over to straddle my legs, sitting on my thighs. She continued to watch me as she reached down again between her legs to rub herself.

She did this for a minute before taking my cock from me and scooted herself forward so she was positioned over my cock. She then leaned forward while still reaching beneath to bring my cock to her opening and slid down on it. I noticed her wince. I assumed she was still pretty sore.

Cindy sat upright and leaned back a bit. I could feel myself deep in her as she started rubbing her clit in front of me. She leaned back some more and supported herself with her other hand on the bed. My cock was stretched to a point I didn't know if it could bend down any further, but I assumed it likely pressed nicely into her upper wall.

Cindy looked me in the eyes as she opened her lips with her index and ring finger while rubbing her clit with her middle finger. It was an amazing sight.

"Okay Greg."

Did she just call me Greg?

"I want to get off with this cock in me, and I want to feel you come at the same time. Do you think we can do that?"

"I can try. I don't usually last long in this position."

"That's okay. I'm really close."

She started rubbing a little more vigorously and added a little bounce to her body which was triggering my cock. I started thrusting myself up with the little movement I could make in this position. I wanted to grab her tits, but they were out of reach with how far back she was leaning, so I rested my hands on her thighs.

In my peripheral view, I could've sworn I saw a shadow in the hall. I wondered if Jules was checking on us or maybe had been out there listening the whole time. I had a split second thought of her joining us.

At that moment, Cindy really started rocking on me. I continued to do what I could to fuck her from underneath.

"Here we go Mr. Schuster. I'm going to c..."

Before she could finish, I felt her body tense and her pussy gripped my cock. She threw herself forward now leaning on her hand in front of her by my shoulder and she continued to rub her clit between her clenched legs. I slid my hands from her thighs to her ass to push her down onto me repeatedly as my body also went ridged and I pulsated inside of her, grunting loudly.

"Fuck yes Greg! I love coming on your cock while you fill me with your cum!"

As we came down from our mutual orgasm, I wondered at her switching between my names. She had previously only wanted to use Mr. Schuster, but now that we've truly been together it seemed she became more comfortable using Greg.

Cindy collapsed next to me to and wrapped herself around me nestling her head in my neck and upper chest. We laid like that for a minute or two before she kissed my neck and then lips.

She then said, "Thank you Mr. Schuster. This was the best lesson yet, but I need to go. My mom is probably wondering where I'm at."

I said, "You're welcome Cindy." as she quickly walked out of the room. I took notice of her saying 'best lesson yet' meaning she wasn't entirely done with me.

Out in the hall I heard her give a giddy squeal to what I assumed was Jules waiting outside. Confirming my assumption, Jules entered the room and sat back on the bed.

"So how was it Mr. Schuster?" Jules asked in a slightly mocking tone.

"It was good actually."

"Great. Now get the fuck out."

I was shocked by this reaction.

"What? Are you upset with me?"

"Yeah... No... I don't know. Tonight has been a lot and I need to reset. When she's done cleaning up, you'll walk her home like a gentleman and we'll start over another time when I'm ready."

This stung. I felt bad for how this played out. I didn't mean to hurt her, if that what this was.

"Okay. I'm..." I stopped myself before finishing my apology. "Okay."

I got up and started putting my clothes back on. Jules sat silently on the bed for a beat before leaving the room and heading downstairs.