Virgin Gigolo Ch. 05

"Yeah," she nodded, and I handed her the condom, moving my erection back up towards her face. "I haven't needed or used a rubber since before Robin was born. Do you always use them?"

"Always," I confirmed as she rolled it over my erection. As soon as she had the raincoat in place, she rolled away from me and off the bed, moving naked across the room to the dresser and her purse which I hadn't really noticed before. Reaching in, she pulled out a small squeeze bottle and turned back, stepping over to the easy chair in the corner and beckoning me to join her.

She handed me the bottle. "This is lube. I would normally do it before I got this far but didn't want to do it at work, so you need to lube my ass and your cock, and then I'll guide you in. You have to take it easy until I get used to you, OK?" Turning, she knelt in the chair, extending her ass up and backwards toward me and dropping her arms and shoulders to the armrests. In this position her ass was naturally spread, her rosebud totally visible, her meaty labia accented between her legs. I could have easily slipped into her vagina and done her doggie style in this position but instead followed her directions.

"Just dribble it on and spread it around," she instructed. I put several drops around her anus, rubbing up and around. "Work some in," she said, "use your finger." I did, pushing right on her rosebud. "Yeah, that's it. Now push harder, work the lube inside."

"In your ass?"

"In my ass. Lots of lube. Put your finger in as far as you can."

I could feel her ass pushing back, pushing against my finger, and surprisingly her ass seemed to open right up, allowing my finger inside her. I wasn't sure what to expect, but I really felt nothing. Unlike a vagina, the tension seemed only to be on the sphincter muscle; it seemed like there was a large, thankfully empty, cavity inside. "Oh My God... it's been so long." I wasn't sure what to do now, slowly began working my finger back out and then moved it inward again -- finger fucking her ass. "More lube, make it really slippery if you can." I dribbled a few more drops around, and she said, "Now your thumb."

"My thumb?"

"It's bigger."

"Oh."

I did as she requested pushing my thumb in as far as I could, clear up through the base knuckle, the largest part of my thumb, eliciting a groan of satisfaction from her, until she said. "Oh... I'm ready... Add some lube to your cock and I want you in my ass."

Making sure the end of my cock was well lubed, I pressed it against her asshole. Just as with my finger and thumb I could feel her pressing back, but my cock was easily twice as big around as my thumb. Still, I felt her ass opening to accept me, and suddenly, I popped through and into her rectum. "OH! Just hold still for a minute!" she exclaimed, "Let me get used to it. It's been so long... you feel so big..." she panted. "Ok, slowly to start..." she added a moment or two later... "Yeah, like that. Not too deep... NOT too deep... Ok, better. You can go deeper after I get used to you. Oh My God, I haven't had a cock in my ass in... oh my... oh... twenty-three..." she panted, "twenty-four years..." Minding her "not too deep" instruction I eased my cock into her ass, perhaps only halfway, before slowly easing back out. "More lube," she instructed. She had been mostly on all fours, presenting her ass to me, but now lowered a shoulder to the chair, her arm snaking back underneath herself to her pussy. "Ok, I'm ready, faster now. I need to..." she shuddered; I realized her fingers had found her clit.

I didn't need a bunch of instruction from here on. My cock was in a tight space, her sphincter gradually loosening up as I slid in and out. I started shallow but naturally began going deeper as I took up a faster fucking motion. I hadn't expected it when her body began to quiver and shake in orgasm, her bottom pushing back toward me every time I moved into her, an "Oh... Oh... Oh..." with every thrust. The stimulation on my cock wasn't that great, just around the shaft and barely any on my cock head at all. I could feel it, and although she wasn't going to get me off very fast, her orgasm continued, and if anything -- got stronger. Her "Oh...Oh... Oh," turned into and "Oh fuck... OH FUCK!... OH my God!... OH Fuck..." We continued for perhaps five minutes, until her hand pulled away from her clit, reached around her hip and, her entire body still quivering, her hand reached for me, telling me to stop my movements.

I stopped moving, my cock still embedded in her ass, her quivering body quieting until I pulled back, causing another convulsion from her. I started to push back in but her "No! It's too much!" told me to hold still. I pulled back, so my cock head was just inside her sphincter and then, after a moment or two, pulled out. "OH!" she said, this time her moan a protest, "you felt so good." She pushed back into an upright position, onto her knees, and I moved back, allowing her to stand. She faltered, nearly falling, but I grabbed her arm, and she turned and moved toward the bed. She fell forward, and then looked back at me, seeing the condom still covering my cock. "Get rid of that thing, and come up here and hold me."

I did as she asked and, since I hadn't cum myself, at least for the moment I was still hard. When I returned from disposing of the condom, she was in a fetal position, and when I crawled up behind her, she pulled my arm over her shoulder and between her breasts.

I felt her slowly begin to relax and with my hand between her breasts it was easy to raise it to her breast, filling my hand, and fondling her nipple. She didn't initially say anything.

"Oh my God," she said, "I'd forgotten how that wears me out."

"I take it you came?" I asked, "I could tell you liked it but couldn't tell when you did."

"Are you kidding? I was coming that entire time. I can come with fucking, but nothing like that. It just goes on and on and on...." She let out a long exhale. "Did you cum?"

"No."

"Oh. Sorry."

"No need to be sorry, this was for you." We lay there for perhaps five minutes before she said, "Come on, let's go take a shower."

Rolling away and standing, she reached back for my hand. I stood and walked with her to the bathroom. "No matter how much I like that, I always feel like I need to shower and clean up afterward," she said as she reached in and started the shower. "My butt always feels slimy until I do."

I took the soap from her and soaped up her body, spending more time than I needed on her ample breasts, but when I slid my hands onto her bottom, she stopped me before I ran a soapy finger into the crack. "I'm going to be sore back there tomorrow but, My God, was that worth it." She took the soap and I watched as she ran more soap suds between her ass cheeks, her own finger caressing and then rinsed thoroughly.

When I turned to step out of the shower, as she was turning it off, she said, "Give me a minute to use the toilet and I'll be right out." I sat on the bed; my cock having wilted slightly. I was thinking maybe I should stroke myself to get hard when after just a few moments she stepped out of the bath wearing just the pale pink blouse that she'd been wearing when I arrived at the room. Extending to her crotch, it was obvious she was totally naked beneath. I'd recognized when I first saw it that it was at least semi-translucent, the decorative lace of her bra visible where it was pressed against the material, but also that her skin had been visible where it touched. Now my attention was drawn to her nipples, no longer hidden by her bra, and deliciously displayed through the material, and her naked pussy peaking from beneath the hem.

"Didn't think I heard you, did you?" she asked as she stepped up to me, stopping just in front of me. I remembered saying that her shirt would look good without a bra.

"Wow," I said, reaching up to both breasts, squeezing her breasts gently through the shirt, my fingers finding and pinching down on both nipples. "As I thought, very nice without a bra. Very sexy."

"I'm glad you think so," she replied, as she leaned down, rested both hands on my knees, and then leaning still further took my cock into her mouth. The way she was leaning on me I had no problem slipping the buttons on her blouse once again, moving the material away and fondling her bare breasts.

"Great tits," I said a few moments later. "This blouse is really sexy like this."

"I'm glad," she repeated, pulling away from my cock with her mouth, reaching for it with one hand to hold me upright. "Every woman likes to feel sexy. Have you got another condom?"

"Of course," I replied, but was unable to retrieve it immediately as she leaned down and took just the head of my cock in her mouth again, holding me upright with one hand. Now loving on my cock with her tongue and lips, I recognized that she was well experienced in giving head. Her tongue moistened my glans before her lips slid over the rim, her tongue swirling around, tantalizing for just a few moments before she pulled back again and said, "What do you think they would say to this?"

"They who?" I responded, baffled. "To what?"

"Robin and Lori, of course," she pulled off and answered with a giggle, immediately slipping her lips back around my cock head.

"Who's Lori?" I puzzled aloud.

"Lori? Robin's old cheerleading buddy? At Helen's party, they were talking about what it would be like to do you. Do you suppose," she giggled, "they had any idea that I would like to do you too?"

"They were saying that?" I questioned, reaching down and twiddling Martha's nipples again. "Seems strange that they were talking that way, or at least Robin was, around her mother."

"We're pretty tight that way..."

"Yeah, I guess. If you went with her to wax your pussy..."

"Do you like it?"

"I do. Very sexy," I said, sliding my hand down to finger her, playing with her labia. "I liked eating you with it naked." She spread her legs, inviting my touch, and again took me into her mouth until she asked about another condom. It was just a moment or two later that she pulled away and said, "Why don't you get it?"

I did, rolling off the bed to retrieve it from my pants pocket. As soon as I did, she climbed onto the bed over me, straddling my legs, and reached for the condom in my hand. "Let me," she said, taking it, lifting my cock upright and again rolling the condom down onto my erection. As soon as she was done, she held my cock upright, rose a bit herself, and slid down onto me.

With her riding me cowgirl, my hands were free to play with her breasts, which I did. I fondled her through the blouse, rubbing her nipples through the silky material but also slipping my fingers up underneath to caress them directly so my eyes and hands could feast on her. I let my fingers slip down between her labia, at first rubbing up and across her clit with my fingers until I turned my hand over to press it against her body and let my thumb caress her clit. As continually aroused as I'd been since I got there, without having cum yet, her bouncing up and down on my cock was all it took for me and my body began filling the condom in her pussy. In this position I could keep the pressure on my pelvis, keeping my erection going, and soon I recognized the quivers beginning in her body. When her two hands came up to play with her own nipples, pushing mine away, I increased the pressure around her clit with my thumb until she began shaking and shuddering. Unlike when I was in her ass, her hand came down and pushed against me, telling me to stop. Apparently sated, for the moment, she climbed off and lay down next to me. I had my arm out; she cuddled against my chest, and relaxed -- I thought she was going to fall asleep.

"That was really nice," she whispered.

"Glad I could be of service", I laughed quietly. She didn't say anything for a few moments; we just lay there. I felt her body relaxing, her heart slowing, until she inhaled and let out a long, satisfied breath.

"Why did you hate Robin?"

"What?" I said, taken aback at the question of which the opposite was the truth. "Me? Hate Robin?"

"That's what she always thought. She said you always just headed the other way and ignored her whenever we were around."

"Oh my God, no. If anything, it was the other way around. I thought I had no chance with a girl like Robin. I always thought she was too far out of my league. The head cheerleader, the girl with the star quarterback boyfriend..."

"You'd have been a lot better for her than that... dick... she dated." She giggled, "My God, I think he almost ruined her," she said, reaching over and once again gripping my now flaccid cock. "He may have been bigger, but I don't think he had anything on knowing how to use it like you do."

I remembered overhearing Martha on the phone telling my mother about seeing Robin and Adam, who I assumed was the dick she was referring to, but I didn't think she knew that I knew. "Adam?" I questioned innocently.

"Oh my God, did you know him? I came home early one day and found them fucking on the living room floor. That kid had the biggest dick."

"And you saw it?" Her nod confirmed what I was asking.

"He was a dick too. They weren't actually fucking when I got there, she was giving him a blow job at first, but then when he got close, he had her climb on and ride him cowgirl." She shook her head. "He was, to say the least, well endowed. But he thought he was God's gift to women, so he treated her like dirt. Best thing she ever did was to break up with him." It was me who nodded in understanding this time.

"Robin..." I said, bringing the conversation back to where it had started. "I didn't hate her. Just the opposite. She was always my fantasy girl growing up, just... unattainable for me. I always felt like she wanted nothing to do with me. When she was around, I always felt that I was just a 'nerd,' just some dweeby son of her mom's friend. I always thought she didn't like me. When I danced with her at her wedding, she wouldn't even let me hold her. Not close at least.

"You never knew she had a bit of a thing for you? I suspect, even then, she was thinking that maybe you were a better match than the guy she had just married. You were a bit younger, but that makes less and less difference as we get older. But she always told me she thought you didn't like her."

I laughed. "I guess I can tell you now, but I used to masturbate to thoughts of your daughter."

"No, she didn't dislike you," Martha said moving back to my previous sentence; "she always had a bit of a crush on you." She giggled. "I know she'd be upset if she knew I got you and she didn't." We lay there quietly for a moment, me thinking about the revelation that Robin really hadn't hated me. I wondered what might have been if I hadn't been such a dweeb, if I'd had the self-confidence to take the first step, even to just say hello.

Martha shifted on the bed, her hand reaching behind herself. "Oh my. That was all well worth it, but I think I might walk a bit funny tomorrow."

"Hurt?"

"No, not really. But I can still feel you up there." She rolled over and looked at the clock. "Oh wow, that went quick. It's time for me to go. My husband will be wondering where I am." She rolled onto her side, toward me. "You were really good."

"Thanks."

I waited for 5 minutes after Martha walked out before I left, just in case we saw someone we knew, but all the time thinking about what had transpired. I couldn't help but wonder what my mother would think if she knew I'd just fucked one of her best friends, especially that I'd fucked her in the ass. A shudder went through me, as the off kilter thought of wondering if my mom and dad did anal sex, admitting that if they did -- I really didn't want to know. My mind shifted to Robin, evaluating that Martha had said she'd always had a bit of a thing for me, just as I had for her.