I met Kerry’s mom first, not long after the two women moved in across the street. Kerry had left for college and I helped her mother out a few times, mostly with heavy lifting. Mom was my age and a fine looking woman, but Kerry was something else—prime fantasy material.
Kerry was no tomboy, but she could work hard, physically. It was summer, after her first year of college, and she’d worked up a sweat mowing her lawn. I was putting flashing around my foundation and struggling to get both ends of a long strip under shingles. I saw her watching, and I called out, “Would you mind giving me a hand?”
We’d never met, and she seemed uncertain, but she came anyway. Her walk was saucy, though I’m sure she wasn’t putting on a show. We introduced ourselves, and I told her I'd helped her mom out a couple of times. I wanted her to know that I’d met her mom and her mom was comfortable around me.
Kerry looked at the strip of flashing, half in, and she knew right away what I needed, at least as far as the flashing was concerned. She got on her knees and helped me work the flashing into position.
“Good job,” I told her when the strip was nailed. Then I asked if she'd be interested in working with me for a couple of hours, for pay. I made her a generous offer and told her I’d give her a bonus if she “helped me get it all up.” I regretted my choice of words, but I kept a straight face, and she did too.
“I could use the money,” she said. “Thanks, I'll go tell my mom where I'm going to be.”
It was hard not being lecherous, but I don’t get many opportunities to be near teenage women. I kept imagining her naked, but it wasn’t just her looks that got me going. Even talking with her aroused me. She was already helping me get it up, not that I ever had a problem in that area.
Kerry was good with her hands, and we worked together the rest of the day and got to know each other. The work required her to bend over a lot, and the view down her shirt was unavoidable. It was obvious to both of us, I’m sure, and her summer-weight bra made the scenery all the more tantalizing. I tried not to stare and she didn’t try to hide anything. We just kept working. The shape of her cute butt and the swelling between her legs, displayed by her tight shorts, was a bonus. At least, that view I could admire from behind, where she wouldn't notice.
When we were done I paid her and we shook hands. I liked touching her.
After dinner I was watching a ballgame when my doorbell rang. I muted the TV and went to see who it was. It was Kerry, dressed up pretty, made up, and holding a purse.
“I was going clubbing,” she said, “but I don’t really feel like it. Can I come in?”
I looked across to her house. “My mom’s not home,” Kerry said. “She’s staying overnight with her boyfriend. And, anyway, I’m pretty much on my own now, and my mom’s okay with that.”
The implications of Kerry showing up, what she said, and how she was dressed had my head full of ideas. I stood, speechless and rooted, but my senses raced as I noted that her taste in clothes was excellent; how she filled them, sublime; and my condition wasn't helped by the perfume wafting from her skin to pierce primitive systems in my brain.
My hesitation embarrassed her. “I’m sorry,” she said. “I guess this wasn’t a good idea.” She started to turn away.
My arm rose, reflexively, and I touched her so she wouldn’t leave. “I’m sorry,” I said. “Please come in.”
She came inside, and I discretely locked the door behind her. She looked around as I led her to the living room and turned off the ballgame.
We sat across from each other. Her dress was short, and it was hard not to stare at the dark space between her legs. I wondered what she had on underneath, or didn’t. I began to think about her clubbing and of girls, at clubs, who got thrills by exposing themselves. I wondered what it would be like to go clubbing with Kerry and to get her drunk enough to be giggly and then to bring her home. Then I started wondering why Kerry wanted to hang out with me, instead of kids her own age, and I also began to wonder how Kerry expected to get
to a club—I hadn’t noticed her mom’s car outside. I stood and walked to a front window and double-checked. Mom’s car wasn’t in sight.
I’ve never been good at small talk or beating around the bush. I've even been called blunt, but I think being direct is being honest. “Did you tell whoever was going to give you a ride that you changed your mind?” I asked.
, I thought.
“Were you really going clubbing?” I asked.
She looked guilty and shook her head no
. I shook my head yes
“I’m flattered that you’d come to see me, dressed so beautifully.” I looked her up and down again. “You’re very pretty.”
I waited, hoping for her to explain herself, but at that point it was she
who was speechless.
“I’m twice your age,” I said. “I don't want to make assumptions. I can’t come on to you, if that’s what you intended, unless I’m sure you want me to.”
She had a hard time with that. I guess being direct wasn't her thing.
“You must be about nineteen, and I’m almost forty,” I said. “Do you want to talk about why you came over?”
She looked, shyly, down at her legs and said: “I’m a virgin. I don’t want to be, anymore.”
That took me aback. I pursed my lips and let out a long breath. “I’m honored,” I said. I really did feel honored. “Are you sure you want me to be the one?”
“We had a good time together, today.
I like you.” Then, after a pause she said, “My friends kid me about being nineteen and being a virgin. They’re always trying to fix me up, with some guy or other, just so I can have sex. But I never met a guy I wanted to do it with. It always seemed like it should be more special. I guess I just wasn't ready. But…” She looked up. “Working with you made me feel sexy. You respected that I was doing a good job. We had a good time together today,” she repeated.
I walked behind Kerry and knelt. I caressed her neck with my fingertips, and I kissed her cheek. She turned, and I kissed her lips. “You are
special,” I said.
“Thank you.” She had tears in her eyes.
It was clear she wanted me to take the lead, and I did. I took her hand and led her to my bedroom. It was masculine, but, hey, a man is what she wanted.
I had her lie on my bed, and I put two pillows under her head, pulled her hem down, primly, and covered her with a blanket to keep her warm and help her relax. I lit two candles and turned out the light, and I got her a snifter with a little brandy in it. Yeah, sure, I know. She’s not twenty-one, so while I can fuck her, I'm not suppose to give her a little brandy to help her relax for her first time. Go ahead and shoot me.
She sipped and smiled, which made my penis rise with anticipation, but I was enjoying what I was doing too much to rush. I decided to draw her a hot bath.
As the tub filled I lay next to her, on top of the covers, with my arm under her head. I caressed her shoulder, and she laid her head on my chest. I slid my hand downward and rested it on the side of her breast. My other hand caressed her hair, her lips, and her cheek. I kissed in her ear, which made her squirm. After awhile she lifted her dress and sandwiched my leg between hers and began to squeeze, rhythmically. My hard penis rubbed against her.
“I’m going to turn off the bath,” I said. “Then I’ll undress you.”
“Mmm,” she murmured. Her eyes were closed. She was breathing deeply.
I turned off the bath and came back to the bedroom. I folded down the covers and turned her over. I lowered her zipper and opened her dress and looked at the strap of her bra. It was black, not the one she’d been working in, which was pale blue. I opened the clasp and turned her front side up.
“I love taking your clothes off,” I said.
“I can tell,” she replied as she gave my penis a rub, through my jeans, with the backs of her fingers. I took her arms out of her dress and lowered it to her waist. Then I took off her bra.
“Whew,” I said, looking at her young woman’s body. Even laying on her back her breasts stood proudly. Her nipples were partly aroused, and I studied their tight flesh. They had the cutest little dimples in their tips. I wanted to suck them, badly, but if I started that I didn’t think I could have resisted fucking her right away, and I’d never get her into the bath, which I was looking forward to. I decided to save most of playing with her nipples for later, but I did run my fingers over them. She gasped and grabbed my hands—her nipples were very sensitive. I took my hands from her and kissed her lips. Then I stood and took the covers all the way off, and I started lowering her dress toward her feet.
She lifted, to help, and then her dress was off, and she lay in panties that matched the bra I'd removed. I placed my fingers in her waistband, and I slid her panties down and off. She opened her legs to let me look but not so much as to abandon all her modesty. It was my turn to smile. “You’re more than very pretty,” I said. Then I slid an arm under her knees, my other arm under her back, and I lifted her to my chest.
She gasped in surprise, and her eyes opened wide. “You don’t have to do any more work today,” I said. “I’m at your service.” I carried Kerry toward the bath.
I can’t claim to be an expert on women, but I’ve had my share of fun, and I’ve learned a few things, over the years. For one, making love with a woman her first time is rarely about breaking a barrier. Usually, that disappears on its own. What are most important for avoiding discomfort are relaxation and lubrication. That’s what the bath and taking it slow were all about.
I’d lit the bathroom, too, with candles, and I sat Kerry on the edge of the tub and caressed her as she sank into the hot water. I continued to caress her as she soaked, and I told her stories, mostly about stupid things I did in college. Then I began to wash her with a soft cloth.
I leaning her forward, supporting her weight on my arm and began to wash her back from her hips, up her sides, to her shoulders, and from her sacrum, up her spine, to her neck. I moved in circular motions, using only water, and I rubbed away old layers leaving fresh sensitive skin in its place. I scrubbed her shoulders and the nape of her neck.
“Try not to get my hair wet,” she murmured. I did my best, to comply.
I leaned her backward and took each of her hands, in turn, and washed between her fingers then raised her arm and washed its length, being careful in the hollow beneath her arm, for she was ticklish there.
I washed in her ears and then her nose, eyes, and cheeks. I washed her chin and then her pretty lips, which I kissed for the third time that day. She kissed me back, and then I began to wash her front
I've always been more aroused touching a woman and giving her pleasure than by having her touch me, and what I did for Kerry, that day, was supremely gratifying. To be a man, in his prime, yet not young, and to have free reign to see and touch and hold a young woman like Kerry and to treat her in a sensitively and caring way… It's a moment that makes life worth living.
I washed between her breasts and down to her abdomen and then came up each side. Then I held each breast, from below, and washed the sides of her breasts and above her nipples. Then alternating hands, one with a washrag and one without, and I lifted and washed the bottom of each breast. Then, with an impish grin and my index finger wrapped in the washrag, I held each breast and daintily washed her nipples. Kerry squirmed and laughed—she caught the humor. “When you do that I feel it right between my legs,” she said.
Lifting each leg I washed her feet and toes and washed my way up to her thighs. Each caress of an inner thigh elicited a gasp and moan, and I rewarded her by sliding my cloth covered hand onto her vulva and giving her a good-girl squeeze. That drove her wild, and my penis surged in sympathy, swelling with jolts of hardness.
Almost done, I washed her vulva, but didn't linger. Kerry was aroused, her swollen clitoral shaft clearly visible between her labia. No way did I want her to orgasm before I was in her.
Finally, I washed her buttocks and between them, treating her sensitive rosette to an insistent stimulating rub.
I was done with her washing, and I left Kerry to relax in the hot water. I lay on my bed and waited, thinking of how lucky I was. Or maybe it’s not all luck
, I thought. Nice guys don’t always finish last
. I took out my penis, which was begging for attention, and I held it in my fist and pushed downward, stretching my skin delightfully. Soon you’ll have your way with her
, I said to it.
I put my penis back and came for Kerry and had her stand, and I dried her thoroughly, all over. Then I lifted her again and carried her to the bedroom and laid her on the bed.
I undressed. My penis stood tall. She looked at it with fascination, and when I came close she took it in her soft hand and stroked its length, making it twitch with desire.
I got on the bed, Kerry spread her legs, and I knelt between them. I stroked the insides of her thighs and up onto her vulva, and I teased her clitoris, which was begging for attention just like my penis.
I lay on her, letting her feel my weight. “Am I hurting you?” I asked.
“No,” she said. “You feel good.”
My penis nuzzled in her crease as I kissed her face, her neck, and her breasts and caressed her sides and under her legs—everywhere I could reach. Then I suckled her nipples, which I'd been aching to do for so long. She loved that.
I felt her wetness as I slid up and down, preparing to enter. “I’m on the pill,” she said. “Vasectomy,” I replied, and I pushed in.
“Ohhhh,” she squealed, gripping my back with her nails. “Ohh, Ohhhh,” she cried again.
I hadn’t entered all the way—I could have—she was wet enough, but I love to tease. And, the leading inch in which a woman is first penetrated is such a thrill. It’s the moment you know, Yes, I really am gong to get laid
, as you revel in the exquisite pleasure of your penis being wetted and squeezed by the real thing. Fuck
, it felt so good I came out did it again, a couple of times, but then I couldn’t stand not being all the way in her, and I sank to the hilt in her hot wet depths.
“Ahhhh,” she screamed and started thrusting, fucking herself on the hard penis deep inside her. But I wanted to be in charge, and I spread her legs and moved toward her, changing my angle to better stimulate her clitoris as I pumped in and out.
I alternated between slow, dreamy, and loving and fast, furious, and demanding; and Kerry responded with gasps and moans and displays of emotion over which she had little control, all of which hardened my penis to a pulsing ingot of iron. It was so hard it hurt, and I knew only coming would make the hurt go away, but I didn’t go there. Not yet. Each time I started to lose control I rested. Then I resumed, and after building and pushing her closer and closer I drove Kerry into climax, and she screamed, while we pumped her to an orgasm that had to be the best of her young life. Her whole body shook—tremors coursed the length of her as she came, again and again, over the course of minutes, stopping and resuming and crying out as she was overtaken by new waves of pleasure radiating from her overstimulated pussy, my penis thrusting in and out as she desired.
After multiple orgasms and countless additional spasms she lay limp, sweat covered, and exhausted. “Oh God,” she gasped as she struggled for breath. But I was in no mood for a reprieve. The time for Mr. Nice Guy
was Not Now
, and I took off like a high performance engine heading for the red line. I swear I must have reached 10,000 RPM when I peaked… “Fuck
,” I shouted as I pushed full in, getting ready to release my load… And then I waited those exquisite seconds while the pump charged to full pressure… And I exploded and shot a full load, and then some, into Kerry’s tight cunt pulsing again with spasms doing their best to milk every last drop of jism right the fuck out of me.
It was a night to remember. We turned on our sides and hugged, and I stayed inside her as we drifted in and out of the dreaminess of post coital highs. Then I pulled out, and we lay together and snuggled.
We slept until the middle of the night and made love again. And we made love a third time, in the morning, with sunlight streaming in on us.
When it was time for Kerry to go she stuffed her bra and panties into her purse, and I helped her slip on her dress. Her high breasts and perky nipples, even after a full night of revelry, still advertised Kerry’s sexuality, and I couldn’t help but fondle her once again as I walked Kerry toward the door.
“Thank you so much,” I said. “You gave me a great gift, even more than what I did for you.”
She lowered her eyes and looked embarrassed, and she confessed. “I wasn’t really a virgin,” she said. “But my mom thought you might not go to bed with me because of our ages. She said you’re, ‘too nice a guy to take advantage of a young woman,’ and if I really wanted to do it with you I should, ‘make you an offer you couldn’t refuse.’”
“Unbelievable,” I replied, shaking my head.
“Well, would you have? Gone to bed with me? If I wasn’t a virgin?”
“Absolutely,” I said without a moment's hesitation. “But I would
have felt guilty about it. But I won’t now, you little… And your mom knew about this all along? Unbelievable. How am I ever going to look her in the eye?”
“She really doesn't mind, you know… Actually, I think she's a little jealous. She likes you too. She told me not to tell you, but, if this helps, she said she’d go to bed with you herself if it wasn’t for her boyfriend.”
I didn’t know what to make of that, but I definitely
filed it away for future reference.
Kerry kissed me on the cheek and started to walk away, but she came back. “I haven’t slept with many guys,” she said. “Just two, before you, and neither of them was like you. I got so horny when we were working together. It was the way you kept looking at me and that you appreciated that I was doing a good job, and you told me so. And in bed, and before that, with the bath and all… That was really nice. You’re different. In a way it was
my first time; I really feel that way, and I won’t ever forget you.” She pressed into me and kissed me full on the mouth.
“You really are
something special,” I said, shaking my head. “If there’s a next time,” I said, hopefully, “I’ll give you a massage after your bath.”
“I’m going back to school soon,” Kerry said, seriously.
I wondered if she was turning me down. I couldn’t hide my disappointment.
Then her face brightened. “I’ll be back for Christmas. Think up a good present, and I’ll let you give it to me.”
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