Virgin Gigolo Ch. 08

Her condominium was upscale, and upstairs. A gated facility, I had to call her number, and the gate swung open. She'd instructed me specifically where to park, in a "visitors" space, not a numbered space. She answered the door on the first knock, I sensed the peek through the peephole before the door swung open, and I realized that I knew this woman. This was the high-school librarian, the one that had been at Helen's sex toy and lingerie party a few months before.

"Brent?" she smiled, opening the door wide and making no effort to hide herself, "Come on in." I glanced back away from the door, realizing the complex layout gave her a private entryway -- nobody except me could see her.

Maryann was taller, perhaps 5-8, and nicely proportioned. A brunette, she had a pixie haircut with blonde highlights that was quite becoming on her. Her clothes -- were practically non-existent. A sheer top hid nothing, her medium-sized breasts with perky nipples protruding through the sheer material were visible. Her bottom was a thong, also sheer, a narrow landing strip visible extending upward for a couple of inches from her pussy. "I hope you don't mind," she said as she saw me eyeing her up and down, just a quick glance at her body. I absolutely understood that looking at her face was more important than looking at her body so didn't spend too much time looking at her offered body. I knew I was going to be exploring her body momentarily anyway. "I didn't figure there was any need for seduction?" It was a question, and I understood that, despite her brazen attitude, she wasn't sure.

"No," I said with a shake of my head, "I take it you haven't done this before?"

It was her turn to say no. "No, never. I uhm..." she scrunched up her face, "So how does this work?"

"It's all about how you want it to work," I said gently. "Usually you pay me now, and if there's something specific you want me to do, you can tell me. If you want to sit and drink a glass of wine, we can do that. If you want to strip me, or me to strip you, you can say that, and we will. If you want to feel like you're being seduced, I can try and do that. If you want me to just get naked and take you straight away, we can do that, and if you just want to sit and talk, we can do that too."

"Do you have condoms?"

"Of course. Just like American Express, I never leave home without them," I said with a smile.

"Nice line," she smiled and giggled at my comment. She stepped over to a table lamp, picked up a small pile of bills, and handed them to me. I took them without counting, noting that they were mostly fifties and 20s, which seemed unusual as I was normally paid in hundreds. "Sorry for the small bills," she apologized, "it took me a while to collect that much extra."

"Kind of hard on a teacher's salary?" I said, getting the immediate shocked response that I'd expected.

"Oh my God! You're in high school! Oh my God!"

"No Maryann, but I was." I reached out and took her hand. "I graduated two years ago, but I know you're the librarian although I never spent much time in there. I didn't know whether you were going to recognize me or not, so I thought I'd just get it out on the table. I recognized you and Ms. Gangwitch at Helen's party."

"Does Sally know?"

"Sally?" I questioned, "Gangwitch?" I asked, confirming her first name. I don't think I'd ever heard her first name; all we'd ever been allowed to call her in school was "Ms. Gangwitch." "Did she know me, or know that I recognized her?"

Maryann shook her head no.

"I didn't think she recognized me," I laughed, "at least she didn't seem to when I didn't have any clothes on, and I did have a mask, although that day not many of you women were looking at my face anyway, were you?"

She didn't answer, now stepping forward, "I knew I shouldn't do this," she said, reaching for my polo shirt and lifting, pulling it from my pants, "But Sally is going to love it, I can't tell you how many times over the years we've laughed about how fun it would be to do one of you young bucks from school."

I lifted my arms and let her pull my shirt up and over my head. "You're going to tell her?"

"Oh yeah, if you haven't heard from her yet, you will. She's been egging me on to call ever since the party. She said if I did, she would too." I slipped my loafers off by catching the heels with a toe. When I reached for my belt, Maryann stopped me, pushing my hand away. "Oh no, I've been dreaming of this for weeks." She easily pulled my belt loose followed by my zipper, and pushed my pants down. I was commando, my normal state of dress when I went out on a house call, as underwear was generally superfluous. I expected that I'd be spending the next couple of hours naked anyway. My cock flipped up, not yet totally erect, but she sank to her knees, gripping my erection with her hand, and looked at my cock from up close before leaning forward that little bit more and taking me in her mouth.

As usual, all I had to do was watch and listen and I knew what she wanted. She wasn't sucking me to get me off, she was enjoying having a hard cock in her mouth. I was the one getting my cock sucked, she was the one giving a moan of pleasure. Fondling my balls, bobbing on my cock, it wasn't but just a short time before she rose and said "Oh My God, Brent. Get out a condom. I can't wait any longer for you to ride me."

Taking my hand, she led me to the bedroom where she had the bed neatly turned down. I hadn't thought about it until then, but looking around, I realized that everything was in a place, everything was Homes & Gardens perfect. There was nothing in her entire condominium that didn't have a specific place, and it was all put away. That she was anal retentive, or at least OCD, was obvious.

I recognized it was my time to undress her, what little there was of that to do. The sheer top lifted off her head, a shiver going through her as I squeezed her breasts, my fingers finding her already erect nipples. The thong panty I started to slip down and then remembered Melissa saying to slip my hand inside and finger her first before taking it off, and figured perhaps that would apply here, too. Slipping my left hand in toward the center of the panty I did it to Maryann just that way. I lifted the top edge, and slid my fingers against her belly and inside her panty, my fingers slipping down onto her sex. Her eyes closed and she leaned into me, her mouth opening with a shuddering exhale as I fingered her.

It was damp between her lips, but her vagina was practically gushing. Slipping a finger into her, I drew it up between her labia until it dried, and then did it again, reaching her clit while my finger was still wet on the second stroke. "Oh yeah, right there!" She exhaled as my finger caressed her clit. I teased for a few moments before pulling my hand back out, catching the top of her panty and easing it down. I got the panty to her thighs before it came totally free, and then she took one hand and pushed it to her feet.

I bent down and sucked a nipple into my mouth, my hand going back to her pussy once the thong was out of the way. She shifted her weight, her legs spreading a bit wider, her hand coming up to the back of my head to hold me to her breast and nipple. "Oh God, I've needed this," she said, a hum of pleasure emanating from her throat. Slipping my second arm around the small of her back, I lifted and moved her backward a foot and a half to the bed. Setting her down on the bed, I gently pushed her onto her back. Leaning in I kissed her neck, moved to her chest, and continued downward. I had to move my hand from her breast but returned it to her nipple after sucking on it as I continued my journey toward her pussy. Her hips were rocking, her body begging me to tongue her by the time I got there. My fingers plundered her again while my tongue caressed and teased her clit. Teasing and tantalizing to start, I very rapidly went to work to get her off.

It didn't take much more, her body convulsing and rocking in orgasm within seconds. She didn't push away, she didn't beg me to stop, so I continued. Her body was convulsing continuously now, her breathing in a ragged pant until her hand reached down and touched my head, without any strength. I wasn't sure if she wanted me to stop, finally a "S... St... ahh... Stah...." Interpreted as a "stop" and I stopped my tongue from moving. I stayed in place for a moment, my lips wrapped around her clit. One more lick across it, her body convulsing from the touch, and I pulled away.

I'd dropped the condoms to the floor as we'd undressed, and now I turned back, found, and opened one, seeing her watch as I unrolled it onto my cock. If possible, her legs spread even more as I moved back between them, guiding myself into place and slipping inside. She groaned at the intrusion, her head arching back, eyes closed, an "ummmm" of pleasure as I began rocking inside her.

Mindful that she'd just had one orgasm, I had to monitor her responses, but it was obvious this was exactly what she wanted. Her legs spread wide, now wrapped around me to welcome me home until I reached down and lifted her legs onto my shoulders one at a time. With her now almost doubled over it didn't take long until she was shaking in orgasm a second time, her head rolling back and forth as she groaned her pleasure. I felt my own orgasm finally approaching, shoving my cock as deeply into her as I could when, I too, grunted at my cock filling the condom with my spunk.

Panting from the exertion, I just stood there with my cock still hard inside Maryann, although it was rapidly losing its rigidity. I could tell that if I pulled back, I wouldn't be able to reinsert myself right now, but I could feel her pussy squeezing against me. "Oh God, I haven't been fucked that well in years." She looked at my eyes, exhaled, and said, "Will you be able to get hard again? Can we do it another time?"

"Give me some time if you want to fuck again," I said, nodding, "but I can always use my tongue again for now."

Her breathing was slowing down, she didn't say anything for a moment, and then I saw her glance at the nightstand. Looking back at me she said, "Can you stay in me and see if you can reach my phone?"

I glanced at the phone and knew I couldn't reach it directly but was pretty sure that if I slid her along the edge of the bed I could, but the thought crossed my mind of what she would want it for. "I don't want any pictures," I said.

She nodded in return. "No pictures." I grabbed her legs and moved us toward the nightstand until I could reach the phone. I caught it with a finger and moved it closer until I could grab it and handed it to her. My cock had now shrunk, and I almost fell out, but when I straightened up again I squeezed my butt and pelvis, forcing just enough blood back into my dick that I was able to maintain myself in her pussy. She looked at her phone, poked some buttons, and held it to her ear.

"Oh My God, that is the best five hundred dollars I've ever spent..." she said with no explanation when apparently someone answered on the other end. "Uh huh..." she giggled, "Right now... Yeah, he's still in me," she laughed outright. "He just gave me the best fucking I've had in probably five years and we've barely gotten started... Uh, huh... I told him you were going to if I did..." I realized with this she had to be talking to Sally Gangwitch, my senior year English teacher whom I'd always thought had 'bedroom eyes.' I'd never heard of anything untoward about her happening, but somehow, I'd always known that, given the right circumstances, she would have liked to. Would she have fucked a student? I doubted it, but a former student?

I felt my cock beginning to stiffen inside Maryann again, just the sound of her telling her friend about me fucking her being the stimulus. With just a bit of rocking back and forth on my part, my cock continued growing. "Yeah, he remembered us from Helen's party... Uh-huh..." she giggled again, 'but he knew who you were... yeah... No, he's not in high school, but he was," her eyes came up to mine, "and I think he was one of your former students." I nodded, confirming that although I didn't think I'd said it, she'd interpreted it correctly. "Yeah, he knew I'm the librarian... Oh Fuck, Sally... he's getting hard again... He's already gotten me off twice and it's only been half an hour... Oh yeah... yeah! I am... yeah..." she suddenly handed the phone up to me, her hips again beginning to rock with me. I didn't realize she hadn't hung up and was handing me the phone to talk on. "She wants to talk to you," Maryann said as I started to move the phone back towards the nightstand. I glanced at the face and saw it indicated it was connected to "Sally."

"Hello?"

"Are you really fucking Mary right now?"

I haven't ever really been one to share sexual exploits, but I hadn't brought this up. "Yes." I hadn't expected the sudden hardening of my own cock, but fucking one woman while talking with another about it, added a little stimulation to the events. Never had I realized that sexual arousal is quite so mental.

"You've got your cock in her? Right Now?"

"Yes." I looked into Maryann's face, repeating the question. "She wants to know whether I've got my cock in you right now." I pulled back, my cock once again hard enough to slip in and out of her.

"Oh Fuck yes! My God Sally, you're going to love this!" Maryann said quite loudly.

"And I know you?" Sally said into my ear.

"Probably. But not as Brent."

"What's your name?"

"Brent," I said, "although you might remember me by another name."

"Oh my God, Brent," Maryann groaned, "Hang up the phone and fuck me. Sally can call you on her own." I heard Sally's voice start to say something, but I'd already looked to press the button to hang up.

I tossed the phone to the bed.

~

"You didn't tell me your real name," Sally Gangwitch said when she called me directly later that night. Maryann had said they'd both gotten my phone number from Helen and had egged each other on about calling me, it's just that she'd called first.

"And I won't," I answered, "although if you figure out who I am, I won't deny it."

"Mary said you made her cum five times." I didn't confirm nor deny the statement, if Maryann wanted to tell about her time with me, that was up to her. "You're not going to say anything?"

"Not my place to talk about someone else's personal..." I started to say business, but changed it, "...life."

"That's good. We have to be a bit, uhm, circumspect?"

"We?" I responded, wondering who "we" meant.

"Teachers. We're just people like anyone else. We all have sexual needs and desires, but just let some uptight mother think that we're having a sexual relationship with someone and we'll get accused of leading their children astray."

"Especially if that relationship is with a student?"

"It does. Even if it's a former student."

"Does that happen?"

"All the time, don't you ever see the news? Teachers have eyes, students have eyes, and there are attractions both ways." I thought back on all the salacious articles I'd read about teachers and students having sex, and especially about my own thoughts of Sally Gangwitch's bedroom eyes. How many times had I had to compose myself, to hide my erection, before I could walk out of her classroom back in the day? Of course, back then I'd had an erection most of the time.

"I used to think you were the hottest teacher I ever had."

She didn't say anything for a moment. "Did I know it?"

"I don't know. Maybe. I usually had a hard-on when I left your class."

"I've seen that a few times," she laughed. "I just try to look away and not let them know that I saw they were aroused. Did you ever come on to me?"

"No. Not me. Has that happened?"

"More than once."

"What about you, have you ever... come on to a student?"

"I've been tempted. Some of you young guys are really tempting. But I never did."

"Huh." She didn't offer more, I didn't ask. It was quiet for a moment, neither of us saying anything.

"So, five hundred?"

Sally at first wanted to make a date with me for that evening, but I told her it would have to wait until the following day.

I wondered what she would be wearing, or rather not wearing, assuming that she and Maryann had talked about everything the night before. Whether they had or not, Sally was equally as stunning when she opened her front door for me.

The pink Wicked Weasel outfit wasn't see-through like Maryann's had been, but if anything, it was even sexier. The stretchy material of her halter top was tied between her breasts, the shape of the larger circles of her areolas plainly visible with her erect nipples perking through the center. Her belly was bare, and a matching pink skirt, well below her belly button, ended just below her pussy. Strappy sandals were on her feet, with her longer blonde hair pulled to one side. "Wow, Ms. Gangwitch!" I said as she opened the door, "you look hot!"

She stood stock still, not moving for a moment, looking at my face. A look of bewilderment came over it, her head cocked to one side for a moment and I saw when she realized who I really was. "Danny?"

"So, you do remember me," I said with a smirk. "I don't think Maryann really recognized me, and you didn't seem to remember me last time."

"Last time?" she asked, obviously knocked asunder by recognizing me, and who I really was.

"I was a, uhm... bit less dressed? At Helens?"

She laughed. "Yes, you were certainly that," she agreed, "but perhaps you should call me Sally instead of Ms. Gangwitch. We're not in school any longer."

"I can't say as I ever saw you wear anything like that at school," I laughed, glancing down at her body.

Sally Gangwitch was certainly my fantasy teacher, if not every high school boy's fantasy. She'd been young and sexy, probably mid-twenties at the time, and as hot as any teacher in the school. Now, nearly 5 years later, she had to be about 30, about the same as Melissa.

Her figure had always been fantastic, and she had always dressed immaculately. Most of the time she'd worn pants that exquisitely showed her gorgeous ass when she bent over to help someone at another desk. Her blouses were always professional, but never left any doubt that she had a wonderful bosom. I particularly remembered a silk blouse that she always wore a decorative lace bra with, the decorations showing whenever she moved where it pulled tight across her bosom. Her boobs had occasionally been partially exposed when she had a vee cut blouse on, especially if she bent over, but I'd never seen any hint of nipples or areolas in those clothes. In this outfit, the sexy body inside her clothes was definitely on display -- on display for me.

She laughed. "Can't say as I ever saw you naked at school either."

"Not hardly, not unless you'd come into the gym sometime."

"No," she laughed, "I will admit that some of us teachers used to talk about what it would be like to walk through a sausage fest like that, though."

"You would have certainly had some drooling boys if you'd dressed like this," I said, stepping forward and raising a hand to her breast. The material of the top was soft knitted, and stretchy, material. I easily felt her nipple in the palm of my hand.

"A bit forward, aren't you Danny?" she asked, looking down at my hand on her breast but making no effort to stop me. I pulled my hand back, letting my fingertips pinch down on her nipple.

"Perhaps if we were in school... but I'm not here for tutoring in English. Isn't this what I'm here for?" Reaching up with my other hand I let my fingers caress and tweak her other nipple at the same time, both nipples elongating to my touch.

"Were you really fucking Maryann when we talked yesterday?"