Chapter 55: How To Teach A Virgin

February 9, 1997, Chicago, Illinois

On Sunday morning, after cuddling with Birgit and eating breakfast, I showered and dressed in comfortable clothes, then read the Chicago Tribune until I heard a knock at the front door. I got up and went to the foyer and let Ally into the house.

“I wasn’t sure if I should ring the bell,” she said.

“It would have been OK - nobody is in bed.”

Elyse and her boys were with Eduardo, Maria Cristina was at church with her mom, and Winter had left early to meet some new friends in Lisle to learn to ski on a small hill in Four Lakes Village. The others were up, but home. Ally took off her Winter coat, hat, and mittens, which I put in the coat closet, then she followed me into the house. Having thought about my encounter with Julie the previous Sunday, I’d decided on a different approach, and hoped it was in line with what Ally was expecting.

I led her to the ‘Indian’ room, closed and locked the door, then lit a stick of incense in the bowl in front of Loki.

“Just relax,” I said, pointing to the floor pillows.

She sat down, and I turned on the small stereo and put in a Mozart CD, and turned up the volume just loud enough to mask our conversation against any little snoops who might ‘happen’ to wander by. I sat down on a pillow close to her, but not too close.

“How long do you have?” I asked.

“Jack is on a travel team and they’re playing in Milwaukee. The game is at 10:30am, so the earliest they could be home is about 1:00pm.”

Which gave us about four-and-a-half hours, to be on the safe side.

“Good. That gives us plenty of time. What did you want me to teach you?”

“I thought I told you!” she replied.

I nodded, “Yes, but there are lots of things we can do.”

She smiled, “I thought the teacher decided on the course outline!”

“I suspect there are things we could do you haven’t even thought about.”

“Duh!” Ally laughed. “That’s why I wanted you to teach me!”

“Do you and your friends still refer to ‘bases’?” I asked.

“No, but I know what they mean. Why?”

“I figured that’s how we’ll start - with the bases.”

Ally smiled, “I haven’t even been kissed properly before.”

Which, I felt, had to do more with the persona she projected than the fact that she, like Tracey Jones back in High School, or Jacqui Vickers from the dojo, was carrying about twenty-five or thirty extra pounds.

“May I tell you something without hurting your feelings?” I asked.

She nodded, “Sure. I know I’m fat.”

“Actually, that wasn’t what I was going to say. I was going to suggest changing the way you act, talk, and dress. Personality, in the end, is way more important than a few extra pounds. And you can lose those, if you’re willing to exercise and eat right. I’ve helped several girls get into better shape over the years, through karate, running, and other kinds of exercise.”

“I hate exercise,” she said.

“What about dance? My sister does Jazzercise.”

“What about karate? Do you think I could do that?”

“We do offer free lessons so you can decide.”

“I’ll think about it. How about today’s lessons?”

I nodded and stood up. I got up, took Ally’s hand, helped her up, then led her over to one of the basket chairs. I sat down, helped her curl up in my lap, and put my arms around her. She lifted her face for a kiss and I obliged. Our lips met in a soft kiss, followed by several more, until I felt her lips part slightly and I gently pressed my tongue into her mouth. Our tongues danced softly for a few minutes, and then, advancing to second base, I moved my hand to cup one of her moderately-sized, soft breasts.

I gently kneaded her breast and ran my thumb over her nipple, though separated by her sweater, blouse, and bra. Ally squirmed a bit in my lap, and our kiss grew deeper. We spent a couple of minutes kissing, with me fondling her breast, before I slipped my hand under the sweater, untucked her blouse, and slid my hand up to her lacy bra.

I carefully slipped my fingers inside her bra, cupped her pliant breast, and gently tweaked her nipple with my thumb and forefinger. Ally moaned softly and ran her free hand gently over my rugby shirt, something I often wore on cold days at home. We spent about ten minutes that way, before I helped her from my lap and we moved to the floor pillows.

I reclined on one of the pillows and helped Ally recline against me, and cupped both of her breasts in my hands, gently massaging them while I kissed her neck. After a few minutes, I slid my left hand down across Ally’s stomach, and ran my finger along the seam of her jeans, causing her to shiver.

“Oooh,” she cooed softly.

I ran my finger up and down the seam a few times, then slipped my hand into her loose-fitting jeans, then under her panties, and across soft pubic hair until I came to plump labia. Ally shivered again, and sucked in her breath as I gently ran my finger over her hood, applying gently pressure.

“Yes...” she hissed softly.

I slid my finger down between her plump labia, coating it with her juices, then gently massaged Ally’s clit until she groaned softly and shuddered. I withdrew my hand and pressed my finger into my mouth, tasting her musky juices. I returned my hand to the source, coated it again, and this time put my finger to Ally’s lips. She opened them to allow me to put my finger into her mouth, and she sucked gently. I removed my finger, coated it once more, and put it on my own mouth.

I maneuvered us a bit so that Ally was on her side, then gently took her hand and placed it on my crotch. She held her hand still over my jean-covered erection, and then with encouragement, ran her fingers along my shaft. After a few strokes, she tried to get her hand into my jeans, but given the angle and how we were sitting that wasn’t possible.

“It’s OK to unbutton and unzip them,” I said softly.

Ally fumbled a bit with the button and zipper, but eventually got them, and slipped her hand tentatively under my briefs. She found my erection, and slowly slid one finger down my shaft, then closed her soft hand around me. She stroked gently, then looked up.

“Am I doing it right?”

“Yes,” I nodded.

She smiled, and I kissed her softly, our tongues dancing together while she gently stroked me. After several strokes, she broke the kiss.

“What do I do?” she asked quietly.

“Third base?” I asked.

She bit her lower lip and nodded.

“Well, I think at a minimum you need to let him come out to play.”

Ally giggled, which was my intent, as I could tell she was a bit apprehensive. We moved a bit and I lifted my butt so she could pull down my jeans and briefs.

“Are they all that big?” she asked quietly.

“I’ve never compared, but a long time ago a girlfriend told me I was a bit bigger than average.”

“So how do I give you a blowjob?”

“The best way is to start by kissing and licking.”

“Like the top or... ?”

“The glans, that’s the top, yes, and the shaft, too. After a bit, then take it in your mouth the way you would a popsicle and use your hand the way you were before. Just be careful with your teeth.”

She giggled again, “OK. And that will make it squirt?”

I’d learned, over time, the easiest thing to do was simply ask for what I wanted, so I did.

“Yes. And when that happens, just keep sucking and stroking, and swallow.”

“I’ll try,” she said bashfully.

We kissed, then she lowered her head and planted a soft kiss on my glans, then kissed down the shaft, and then back up. She tentatively licked my glans and kissed it again, which started a sequence of kisses and licks. She used her hand to gently stroke me, eventually exploring my sack, gently cupping it, then squeezing softly. After a few more kisses and licks, she opened her mouth and took in my glans, sucking gently. She bobbed her head, and ran her soft tongue along my shaft.

“Yeah,” I sighed. “Just like that.”

I watched and enjoyed as she continued fellating me, experimenting with the depth of her bobs, the strength of her sucks, and the speed of her strokes as she worked towards the inevitable conclusion.

“Soon,” I whispered as she brought me closer and closer.

A minute later I groaned softly and the first spurt jetted into Ally’s mouth. She squeaked and jumped, coughed a bit, but didn’t stop sucking, bobbing and stroking. When the second spurt pulsed into her mouth, I felt her swallow, which she did each time until I was finished. She sucked once more then released me and looked up.

“Was that OK?”

“More than OK!” I replied with a big smile.

I gently pulled her up and we exchanged a soft French kiss. I broke the kiss a short time later and pulled Ally’s sweater up. She raised her arms and I pulled it over her head and off her arms. I unbuttoned her blouse and helped her remove it, then unclasped her bra. I pushed the straps from her shoulders and let it fall away, revealing her breasts, which were capped by large pink nipples. I lowered my head to one and sucked gently, causing Ally to moan softly. I soon switched to the other one, then released it.

I lifted my head and looked into Ally’s eyes, then moved my hands to her jeans. She smiled nervously as I unbuttoned them and then drew down the zipper. As I had, she lifted her butt so I could pull both her jeans and panties down and off. I quickly removed my rugby shirt, leaving us both naked. I got up, arranged some floor pillows, and then spread a comforter over them. Ally moved onto it and I moved on top of her, my head at the level of her breasts.

I suckled on her left breast for a few minutes, then switched to the right one to do the same. But I wasn’t a breast man, and my preferred activity beckoned, so I released her breast and kissed my way down her stomach, stopped to nuzzle her soft pubic hair, then my tongue ran a complete circuit around her extremely plump labia.

“Oooooh!” Ally sighed.

Next, I ran my tongue down and up along her slit, coating the tip with her juices. I closed my mouth around her hood and sucked gently while pressing my tongue against her clit. Ally shuddered and moaned and gently pushed her hips up to create more pressure. Taking the cue, I slid my hands under her butt, squeezed her soft cheeks, and pulled up as I licked and sucked.

“Ooooh, yes, ooooh!” she moaned, then hissed, “Yes!” as she had her first strong orgasm.

I released her clit and gently probed between her labia, but they were so tight, I had to work a bit to get my tongue between them and into her tunnel, which I attributed to her being tense, despite obviously wanting to have sex. I didn’t detect any signs of a hymen, so I returned to pleasuring her clit, eliciting two more strong orgasms from Ally before I moved up and we exchanged a French kiss. After a minute I broke the kiss and got up.

“What’s wrong?” she asked nervously.

I smiled, “Nothing. I just want to get some lubricant to make your first time easier.”

She nodded and I went over to the shelf where I’d strategically placed the tube of K-Y Jelly. I moved back to where Ally lay, and had her lift her hips so I could move another pillow under them. Next, I uncapped the K-Y Jelly, squirted some on my finger, then gently rubbed it between her labia. I squirted a bit more on my fingers and coated my shaft, and then used a final dollop to liberally coat my glans. I sealed the tube, set it aside, and knelt between Ally’s legs.

I carefully pushed Ally’s knees out as far as possible without being uncomfortable for her, then grasped my shaft and rubbed my glans up and down along her labia several times, then placed the tip of my glans in the right spot and gently pushed forward. I slowly spread her labia and with a bit more pressure, my glans slipped past her tight entrance.

“Oooffff!” Ally exclaimed breathing out hard.

“You OK?”

“Yeah, it just feels like I’m being split in half!”

“Just relax,” I replied with a smile. “Take a few deep breaths and let them out.”

I waited for her to do that, and when I felt her tension reduce a bit, I pushed forward again, gaining perhaps another inch. She was extraordinarily tight, so once again I waited for her to take a few breaths before I pulled back a bit and pushed forward again. It took six more short strokes before I was fully embedded in her and lowered my body onto hers.

“You OK?” I asked.

“Yes,” she gasped. “I think so.”

I kissed her nose and she giggled. I pulled back and then slowly pushed forward again. It was not quite as difficult, but she was certainly the tightest girl I’d been with since Katt’s friend, Laura. When I was fully inside her again, I kissed her softly.

“Wrap your legs around me,” I whispered in her ear.

I felt Ally’s legs close around me high up on my thigh, just below my butt, and she wrapped her arms around my neck. I kissed her softly, slid my tongue into her mouth, and then began slow, measured, intensely pleasurable strokes. After about a dozen, she began raising her hips as I moved forward, and wiggling them when I was fully inside her. I moved my hands under her shoulders and slightly increased the speed and force of my strokes.

Ally broke the kiss and gasped for air.

“It feels soooo good!” she gasped between breaths.

“It does,” I agreed.

Ally’s ultra-tight tunnel had loosened just a bit, allowing me to move a bit faster and harder, and she rocked and wiggled her hips as I pushed into her. Her breathing became ragged, she clenched me tight with her arms and legs as her muscles spasmed and gripped me so tightly I simply stayed deep within her and ground against her clit with my pubic bone.

“Oh fuck!” she groaned loudly.

When her orgasm passed and I could freely move again, I methodically worked to bring her to a second, and then a third, orgasm, Ally groaning ‘Oh fuck!’ each time. As I worked her towards a fourth orgasm, I felt my own building towards the point of no return. I managed, just, to get Ally there before I came, and her intense spasms pushed me over the edge. I came, hard, firing jet after jet deep inside her.

“Oh fuuuuuccckkk!” she gasped. “So goooood!”

When both our orgasms had passed, I carefully withdrew from her, moved to her side, then pulled her to me to cuddle. We lay quietly, with only the sounds of our ragged breathing and the last movement of the Mozart piece breaking the silence. Every so often I kissed Ally’s forehead and she sighed deeply. After about ten minutes, she lifted her head.

“It was amazing,” she said. “Can we do it again?”

I nodded, “Yes, and next time you can be on top.”

“Cool!” she breathed.

She snuggled again for a few minutes, and the CD ended, so I slipped from her arms, put on another classical CD, then snuggled close. A few minutes later, I pushed her gently to her back and pleasured her breasts and clit with my lips and tongue, then lay on my back and pulled her on top of me. I helped her position herself, and I held my shaft as she slowly worked it into her warm, tight, silky folds.

“Just move however feels good,” I instructed. “But lean forward so I can suckle you.”

Ally offered me her left breast which I latched onto, and then she began experimenting, ultimately settling on alternating up and down once and back and forth twice and then repeating. I rested my hands on her hips and enjoyed the motion while I licked and suckled her engorged nipple. Once again, with each of her four orgasms she groaned ‘Oh fuck!’ and ground hard into me, and during her fourth orgasm I erupted, filling her with my hot, sticky cum. Ally ground against me until both our orgasms passed, then collapsed on top of me, breathing hard.

I gently rubbed her back, occasionally cupping her butt, until I softened and slipped from her. She sat up, smiling, then leaned down so we could exchange a soft, sexy French kiss. After a moment she broke the kiss, and lay down on top of me again. I held her loosely in my arms, and rested my ankles on hers. Ally sighed deeply several times while we lay together, then crossed her arms on my chest and rested her chin on them.

“Happy?” I asked.

“Oh my God, yes!” she exclaimed. “And it’s only 9:30am!”

“True,” I replied with a grin. “We have plenty of time to do it again a couple of times!”

“Can you teach me anything else?”

“Well, there’s ‘69’,” I said.

“What’s that?”

“I lick you while you suck me until we both cum.”

“With all your stuff in me?”

“I honestly don’t mind.”

“Now?”

“Just turn so I can put my mouth on you and you can suck me.”

She moved off me, turned around, and straddled my face, lowering her pussy to my lips as she took my flaccid shaft into her mouth. It didn’t take long before I was hard, and we pleasured each other for about twenty-five minutes before I shot off in Ally’s mouth and she swallowed every drop. She released me, turned, and we shared a sloppy French kiss our tongues trading our combined juices. We broke the kiss and snuggled together.

“Can you fuck me twice more before it’s time to go?”

“Yes, and we’ll have time to shower together, too.”

“Can I ask you something?”

“Sure.”

“That thing you did with Mattie? Is that normal?”

“Normal is whatever two people want to do together. People like different things and do different things. And girls can be together, just as guys can be together, or you can have multiple people. But YOU should only ever do what you want, and what YOU think is right.”

“Do you want to do that with me?”

“That’s not the right question,” I replied. “The right question is do YOU want to do that.”

“Do girls enjoy it?”

“Only one girl I know really liked it, others kind of like it or tolerate it, but a lot don’t like it at all.”

“Why?”

“Well, girls pretty much need clitoral or vaginal stimulation, and pleasuring the clitoris is the most likely way to get a girl to have an orgasm. Girls can rub themselves during anal sex which can give them orgasms.”