Kristen needs a sitter... but the situation turns into a wonderful opportunity
I’d known Kristen for almost two years. Our nine year-old sons played soccer on the same team, so we spent many Saturday mornings alongside the field watching them run around after a white ball. We weren’t exactly “good friends”, but we talked every time we met, passed the time of day and consoled each other in our single parent status. My wife had left me for her rich boss and how her husband ran off with a girl from a trailer park. We always laughed about how there was a message in there, but we didn’t know what it was. I liked talking to Kristen, she was always fun and fresh. After all, who doesn’t like talking to beautiful women?
This particular Saturday morning Kristen was looking a little more flustered than her usual self as she arrived at the field and when she finally sent her son off to join the pre-game huddle and unfolded her chair next to mine I had to ask her if she was okay.
“Yes, I guess… fine. Sorry, I’m just a bit out of sorts.” At least she could still smile at me. “On the way over here I got a call from my babysitter, saying she can’t make it tonight. Now I’ve no sitter, no time to find one and a hot date who’ll be stood up.”
Now, I’m no hero, and facilitating another guy being with this lovely creature was not exactly in my nature, but I’m also a sucker for doing a nice lady a favor. “I’ll look after Josh if you like,” I offered. “The boys get on well together, they’ll have fun.”
Kristen seemed a little taken aback at first but her face softened and she asked, “Are you sure?”
“No problem,” I assured her. “I’ll get pizza, we’ll watch a movie or they can play computer games. You know what they’re like. He might as well sleep over if you’re okay with that. Save you worrying about being late tonight. You can pick him up in the morning.”
“I’m sure Josh would have a lot of fun.” She looked over at the boys as they ran on to the field. “If you really don’t mind, that would be great for me.”
I looked into her smiling, brilliant blue eyes and could only feel good that I’d made her happy.
I wasn’t prepared for her turning up at my door dressed as a biker chick.
“It’s a fancy dress party,” she smiled to explain the leathers and torn T-shirt. “We’re going as Hell’s Angels. I tried to get some fake tattoos, but couldn’t find any. You think I’ll do?” She spun on the spot to give me a three-sixty view of her outfit.
Would she do? Well, for me, the tight-fitting leather pants were just amazing. They hugged her thighs and bottom like they were painted on by an expert in perfect female anatomy. Inside her jacket, Kristen’s T-shirt was stretched by her fine chest and I thought I just caught the tell-tale impressions of her nipples that suggested she wasn’t wearing a bra. Her flowing black hair was a little more “up” than normal as she’d worked some vampish body into her normally straight locks. Overall, she looked like a raven-haired version of Olivia Newton-John’s transformation character in Grease.
“You’ll do,” I expressed my approval with an intake of breath. I couldn’t keep myself from imaging how it would be to slide those pants down her silky legs.
Getting back to reality, the boys ran off to the basement to start a digital war on the games console and I reassured Kristen that everything would be just fine and that she should head off and have a great evening. She thanked me with a peck on the cheek and I closed the door behind her feeling like a million dollars. I had just been kissed by Olivia’s double.
I sat in front of the TV and heard the occasional sounds of youthful exuberance as the cyber battle ebbed and flowed below me. It was hard not to let my mind drift off to think about Kristen, dressed to kill and out with another man. Yes I was jealous, but I was the good guy who facilitated my own torture. Or was it my own stupid fault for not asking her out months ago?
She had only been gone an hour or so when my biker chick fantasy arrived back at my door.
Answering the doorbell, I stood there looking puzzled at my leather-clad dream. Kristen still looked stunning, but the exuberance she showed when she last stood on that spot was gone and there were a few tell-tale signs around her eyes that she’d been crying.
Without waiting for me to ask what was wrong she told me, “He didn’t turn up. Can you believe it? There I was in a house with all of his friends, and he doesn’t turn up.” She was trying to put a brave face on it, but failing miserably. “Fucking men. Sorry, I didn’t mean to swear.”
“Don’t worry, a lot of men are assholes.” I tried to smile comfortingly and resist wrapping my arms around her. I couldn’t comprehend any guy who would stand her up. Me? I would crawl miles across broken glass for a date with Kristen. I know, just asking her might’ve been easier, but I never did.
“I thought I’d better come and collect Josh. There’s no point in wasting your time and effort looking after him now.”
I told her it was no problem, and that we’d just ordered the pizza I’d promised for dinner. “Hey, why don’t you stick around and have some with us?”
“What?” Kristen used her arms to indicate her costume. “Dressed like this?” She had brightened up a little though.
I told her it was no problem but she insisted she run home and change. Happy as I was to have my biker chick spend some time with me, I was equally delighted when the Kristen I was more familiar with returned to my door, now in jeans and a gray sweater. Returning her hair to its normal, straighter, style was too much for the quick visit home though, which was just fine for me.
I opened a bottle of wine to have with the pizza which we had in the kitchen, the boys declining to join us in favor of more games in the basement, taking their food with them. Kristen talked about her no-show date. She had seen him a few times and was beginning to think they were headed towards a relationship, but now he was nothing to her. Forty-five minutes after he had arranged to meet her at his friend’s house he called to say he had car troubles and wouldn’t be there. “I thought he was better than most of the others. Why the hell couldn’t he have phoned earlier?” She said wistfully as her second glass of wine emptied. “It’s so hard to find a good partner in this life, don’t you think?”
I laughed and agreed with her. “Just look at us, even when you think you’ve found one, it can all turn sour pretty quickly.”
It was easy to talk to Kristen, and even easier to imagine being naked next to her. Despite the platonic nature of our evening, it was impossible for my fantasies not to arrive at regular intervals as her face brightened with our conversation and not having to spend the evening alone after the pain of her ill-fated date.
As the clock approached ten I thought I’d check on the boys and was surprised to find they had taken it on themselves to unroll sleeping bags in the basement and crash out on the carpet. I called Kristen to come see them asleep. “I never did tell him his sleep over was cancelled,” she giggled.
When we got back upstairs I poured the last of the wine into our glasses and we sat back down at the kitchen table. “That’s neat for Josh.” Kristen smiled as she sipped at her glass. “I think he’s had a really great time.”
“I hope your own evening has improved a bit too?” I asked with a smile that tried not to be too provocative.
“Yes. Thank you.” Kristen smiled and lit a fire that had been missing from my world for too long. “I’ve had a nice time. I think I’d even managed to forget about the disaster of the party,” she laughed.
I had enjoyed having Kristen around and wanted to prolong the evening, so I suggested that if she wasn’t in a rush to go she might like to watch a movie with me. With a wide smile she eagerly agreed. I ushered her to the DVD shelf and left her to choose while I cleared up our pizza debris.
As I loaded the dishwasher I couldn’t help but glance over and see Kristen bent over examining my DVD collection, that shapely bottom of hers that had been so evident in her biker outfit now back on display. When I saw her like that time stopped while I imagined my hands running over those incredible curves. I thought how delicious it would be to slip a hand between her thighs and press myself up against her while I held her hips.
She chose an action comedy and while the movie was starting to play I arrived with a fresh bottle of wine. We sat on a sofa each, separated by a small table, where I placed the wine and a bag of nachos. Kristen’s eyes widened as I started to pour. “Josh won’t be the only one sleeping over if I have any more. I’ve already had too much to drive home.”
“No problem,” I said lightly. “There’s plenty of room.”
We got lost in the movie for a couple of hours, two hours during which I wondered if there was any possibility Kristen’s sleepover might just include sharing my bed. But it all seemed so far-fetched; the thought that she would be anything more than a friend, someone to share some chat, a pizza and a movie. Still, as I glanced over and saw her comfortable pose on my sofa and her smiling face in the half-light, it was hard not to imagine slipping that sweater over her head.
As the credits rolled up the screen we mutually stretched from our relaxed positions and took our glasses into the kitchen. “Are you sure it’s okay to stay over?” Kristen asked sleepily. “I can just crash on the sofa if that’s okay with you.”
I assured her it was okay and that she should sleep in the spare room upstairs. Without listening to her protests of not wanting to be any trouble, I led her upstairs, showed her the room, showed her the bathroom and got her a fresh towel and a new toothbrush. Kristen smiled sheepishly, thanked me and wished me “goodnight”.
I went downstairs to switch everything off and lock up but when I got back upstairs Kristen was standing in the doorway of the bathroom still holding the towel and toothbrush. It was almost like she was waiting for me. I slowed up as I approached her, not sure what to expect.
She tried to smile and appeared to swallow hard as she spoke. “You know, I hope you don’t think this is terrible . . . but it’s been a long time since I’ve been with anyone… and, well, I’ve had a lovely time with you and… I’d really like to spend the rest of the night with you.”
“That’s not terrible.” I slowly approached her, opening my arms to wrap them around her. “That’s a very beautiful thing.” As I folded her in my arms Kristen let her cheek come to rest on the top of my chest. “Anyway,” I gave her warm body a friendly squeeze, “it’s been a long time for me too.”
I led Kristen to my room and she sat down on the bed while I brushed my teeth. She was still clinging to the towel like it was a comforter, when I came back and sat beside her. I could see she was nervous and unsure what to do, but it was easy to sympathize as I was in the same situation. I suggested we simply get on the bed and talk a while. Kristen agreed, and crawled over the bed to lie. I noticed that she’d left the towel behind.
We didn’t talk too much, just nervously mentioned a favorite scene from the movie and giggled a little as I worked my arms around Kristen. We were so close our noses touched as we spoke and the dim light eased some of our nerves as we got used to being close. My senses were heightened to every curve of Kristen’s body as she snuggled to me allowing our thighs to interlock and her chest to warm mine. I was already very excited as she let her hand wander along the side of my torso and I couldn’t resist any longer when I traced my finger across her cheek, I kissed her.
Those first few small kisses of gently pulling at each other’s lips were divine. As we began to taste each other for the first time and out hands caressed more urgently I could feel a lot of the tension begin to leave the air. Looking into Kristen’s beautiful face I whispered, “Shall we take these clothes off? I’d love to feel you next to me.”
She nodded and smiled. She started to reach down and unzip her jeans but I stopped her. “No. Let me do that,” I insisted. “Stand up and let me undress you.”
Giving me a sensuous kiss before she moved, Kristen slowly eased herself off the bed and waited for me to follow her. I stood in front of her for a few moments before I placed my arms around her waist and pulled her close. I’m sure by now she could feel the bulge in my jeans and I let my hands wander over her bottom before retracting them and taking hold of the sides of her sweater and raising it up over her head. This was the moment I’d been thinking about for hours.
Against her tanned skin the white bra she had on underneath the sweater stood out in the half-light. I made no attempt to avert my eyes as I smiled down at her nicely shaped breasts that were being pushed up by the bra. I gently fingered the lacy top edge, feeling the softness of her skin almost tingle under the touch of my fingertips. “You’re so beautiful,” I whispered. All the time I’ve known you I’ve thought that. I’m so glad you’ve decided to stay tonight.”
I knelt in front of her and pulled on the zipper of her jeans. White matching panties peeked at me as the zipper opened. More white was revealed when I popped the button and pulled her jeans open. Before I pulled them down I reached behind her, inside the denim, and cupped her bottom with both hands, letting my hands run over her firm cheeks and enjoy the curves of her body. Kristen stepped out of her jeans when I pulled them to her ankles and I stood up to see her smiling as her chest started to move up and down with her deepening breathing.
I reached behind her and found the fastener for her bra, pulled at it and let it fall loose. It was still covering her as I leaned forward and kissed her, deep and long, tasting her and feeling her desire. When we broke the kiss I gently eased her bra from her shoulders and let it fall. Her breasts were beautiful, round and full, a handful rather than huge. I pushed one upwards and watched as the nipple stood out. I leaned forward and took the other one on my mouth.
Kristen sighed and her hand came around my head in encouragement. “God, it’s been so long.”
She had small, tight nipples, but the one in my mouth was growing quickly as I pushed the soft flesh of her breast and fed it into my mouth. I felt the throbbing of my cock between my legs as I held her with one hand and pleasured her with my tongue and lips.
When I felt her hand ease on my head I stopped sucking on her nipple and slid slowly back down her body until I was on my knees again and facing her panties. I ran my hands around her bottom again, but this time I slipped my fingers inside her panties to feel her skin. When I started to pull her panties down Kristen eased her legs apart to help me. Once they were loose I let them fall and she stepped out of them but I didn’t stand up. I wanted a close-up of her neatly trimmed pussy.
While I looked at her I ran my hands lightly over her thighs, inside and out. As Kristen opened her legs to let me I saw her pussy lips part and reveal a tiny pink glint of her excitement that allowed her scent to musk the air with the sweet smell of her sex. I stood and smiled at her, amazed at the moment and how beautiful she looked.
“You don’t need this anymore.” She started to unbutton my shirt.
I stood there silently enthralled as she slipped away my shirt and ran her hands all over my chest. Mirroring my movements with her, she eased her mouth to my nipple, sucked on it and pulled it with her teeth. It reacted to her touch, firing my desire. By the time she started to unbuckle my belt I felt like I was about to burst out of my pants. Kristen said nothing as she unzipped down the line of my bulge and popped them open. I took a quick look down at myself as she pulled my jeans away from my legs, her breasts moving divinely. The bulge was unmistakable, the head of my cock trying to wriggle under the elastic of my underwear. It was as big as I had ever felt.
Just as I had done for her, she came down to her knees as she started to take off my briefs. Pulling the sides wasn’t going to work as they hooked on the end of me, so she eased them up and over my erection, then away from me altogether. My cock was standing almost straight up from my full balls, firm and begging for the touch of Kristen’s hand. Thankfully it didn’t have to wait too long.
I gasped as her hand gently took hold of my shaft and started to explore its length. Kristen’s other hand eased between my thigh and my balls, easing them outwards so that when she brought her head close enough she could kiss them, then suck them gently. “Nice cock,” she breathed between licks as she started to work up my shaft. I watched her head obscure my cock then I closed my eyes as her mouth closed over me.
As Kristen’s tongue explored me and her hand gently eased back and forth along my length I shivered and tried to breathe deeply as the pleasure washed over me. Feeling her taste me and knowing it was Kristen’s head I was watching work me was the most incredible feeling I’d ever known. As she eased off me and continued to lick me I wondered if I shouldn’t back away in case I came too quickly.
She seemed to sense that, knowing already it was the first time in a long time for both of us, and she stood up, kissing me deeply while still holding me tightly in her hand. Taking the lead now, she eased us back onto the bed and lay facing me, kissing me while both of her hands held my cock and balls.
With one hand massaging her thighs, I eased the other under her neck and started to nibble on the nipple closest to me, feeling it swell and harden between my lips just as its twin had done earlier. I encouraged Kristen to move onto her back so I could play with her other nipple, twisting it gently between my fingers as I sucked and pulled on the other with my mouth. I felt the warmth coming from her pussy before my hand reached it, gently sliding up her thigh and feeling her legs open for me as my fingers traced along her wetness. I felt her breathing pause as my finger slipped between her pussy lips and traced a line along her soaking slit.
“That feels so good,” she breathed. “Do you want to come up here for a while? Let me feel you inside me?”
“It’s okay,” I assured her, “In a little while.”
As I continued sucking, pulling and twisting her nipples with my mouth and hand, I started to slip my finger deeper into the warm silky depths her pussy. Moving slowly in and out of her, I positioned my thumb to massage her clit, feeling it immediately come alive to my touch. When her hips started to want to rise up from the mattress I knew she was close to orgasm. “Relax,” I whispered. “I want this to be beautiful for you.”
Kristen did as I said and allowed me to continue gently moving my finger in and out of her and play with her clit, coating it in her juices as she flowed with the excitement. “Feels so good.” She smiled. “God I’ve missed this so much.” She reached down and took a light hold on my cock. She pulled on it with very short, gentle, strokes, her movements seeming to increase her own pleasure as well as keeping me rock hard and ready for anything.
I felt her relax in my arms and give herself up to my attentions and I went back to sucking on her nipple and pulling it playfully with my teeth. I felt the tension in her body rise quicker than I expected and felt her begin to grind herself into my fingers and raise herself up towards me. Rather than speed up my attentions on her pussy, which was beginning to drip with her flowing sex, I let my fingers rise with her body, keeping the pressure light, and slowed my fingers down. I concentrated my mouth on playing with her nipple in long slow movements of my tongue around it, sucking hard every now and again and pulling it with playful bites.
“Oh God I haven’t felt like this in so long.” Kristen was panting and had her hand pulled on my cock a little more urgently. “You’re going to make me come.”
Pleased as I was to hear that, I already knew it and was smiling up at her as my mouth clamped on her breast. Adding a second finger to move inside her, I felt her gasp again and I knew she was on the brink. As her body tensed I pulled hard on her nipple and probed her as deep as I could. My thumb flicked over her clit slowly, but I added pressure and I knew her moment had arrived.
“Oh… my… God,” she said as the orgasm slowly moved through her, making her pussy contract and then gush. I kept my fingers moving on her and the hand that had been massaging my cock came up and held my hand tight to her pussy while her muscles froze in the throes of her pleasure. As the wave passed over her and she started to relax, her hand left mine and I continued to stroke her dripping pussy while she breathed deeply and giggled to me as the relief of her climax took over from the pleasure.
“That,” she kissed me on the forehead, “was amazing.” Her hand came back to its comfortable position of holding my erection, ringing around the rim of my cock with her thumb and forefinger. “I’m not sure it’s ever felt that good. Not for a long time, that’s for sure. Come on, move over, it’s your turn to lie back and enjoy.”
I shuffled more into the center of the bed and Kristen knelt up so she could pay some detailed attention to my cock. Stroking it along the underside with her open palm, she wriggled her other hand between my legs and sampled my balls, gently squeezing and lightly stroking them. “It’s been a long time since I’ve held one of these,” she giggled. I was willing to testify that she hadn’t lost her touch.
She watched her movements intently as she slowly explored every inch of me, stroking the skin, running her fingertips along me and squeezing around the rim. At the base of my shaft she massaged more deeply, sending wonderful sensations down into my balls. I saw a smile cross her face as she noticed the bead of pre-come that had appeared at the end of my cock. Leaning down, she lowered her mouth and ran her lips along my shaft in a series of kisses that she topped off by her taking the head of my cock into her mouth and covering me with the slow and delicious movements of her wandering tongue. I felt the warmth of her mouth spread all over me as she sucked and licked at me lovingly.
When she popped me out of her mouth I looked down to see the glistening head still firmly in her hand. Kristen’s eyes didn’t leave my cock as she lifted it, stroked it and caressed it. She pulled my cock upright so it was almost vertical from my prone position and licked me up and down again while she let her hand press firmly into my belly and wander around my thighs.
Deciding it was time to take me where she wanted, Kristen eased her leg over me and shuffled her position to straddle me. Now she eased herself up my body to hover over my cock tantalizingly as she continued to hold it straight up. I felt the tip touch her wet lips and looked up at her intensely as her arm was stretched down, holding me and guiding me towards her pussy. Easing the head of my cock into her, she let go of me and placed both of her hands behind her, resting them on my legs just above my knees. Her face, smiling through the sheen of our passion, held my gaze as she lowered herself deliciously onto me.
It’s hard to forget what it feels like to be inside a tight, warm and wet pussy, but after a while it’s hard to remember just how amazing that feeling is. As Kristen began to slowly ease herself on and off me I reached up and took hold of one of her breasts and squeezed it as she squirmed down on my throbbing cock. She threw her head forward into my hand, bringing her own hands forward to rest on my chest. I could see the pleasure on her face as she controlled our movements and as I thought about how incredibly erotic it was watching her enjoy herself on my cock as I felt the first gentle indications of a huge orgasm stir inside me.
She felt it too. “Its okay baby,” Kristen smiled down at me, her bright eyes misting as she eased up and down with her thighs, “it’s your turn now. Come for me.”
The room suddenly seemed brighter and time slowed down as the rush built up inside me. I watched her face as her unblinking eyes studied my every movement so she knew exactly what to do to increase my pleasure. The last thing I remember before my head exploded was how she looked even more beautiful with me inside her.
It was a moment like I’d never imagined. So long since I’d been with a woman, so long since I connected on that hot, steamy level that makes for the best sex. Kristen shifted herself constantly up and down, covering me with her silky pussy and gripping me with a pleasure hold that was blowing my mind. The orgasm built for what seemed like weeks before it arrived with a huge burst of heat, lightness and pleasure.
I heard myself let out a groan of pleasure as the blanket of the orgasm arrived and covered me with sparks and shots of electricity all over my body. I was in the throes of that moment forever when I started to shoot deep into Kristen’s pussy. I saw her smile as she continued to slide up and down and felt my seed fill her. She reached behind her and traced her fingers over my balls as my legs shivered and shook the last of the climax from me. I was smiling too, looking up at my new lover, unable to move yet and my breathing drained by the heart-stopping moment that she had brought for me.
As Kristen slipped off my softening cock she was grinning. Tracing her hands all the way up my chest, she snuggled next to me and I pulled her close with my arm. I whispered through my recovering breath, “You can sleep over any time you like.”
Planting a kiss on the side of my cheek, she laughed a little and said, “What a lovely thought. Mind you, I’m not sure we’ll be getting much sleep.”