Smoking Babysitter

"No," I sighed. I took a puff of my smoke and then leaned over to the ashtray. "I've never been with anyone," I said wistfully as I laid back down.

"And yet," she leaned in closer to me and ran her fingers through my hair. "You knew exactly how to pleasure me."

"Well yeah," I shrugged. "I know how to get myself off, and just sort of did the same thing to you."

"Exactly," she leaned in and kissed me on the cheek. "Women know how to pleasure each other. Even when they're at their best, men can't quite get it that right," she added as she leaned over me and butted her cigarette out.

"Makes sense," I nodded. I finished my cigarette and butted it out. "You certainly did a great job on me too."

"Thanks," she sat up and smiled back at me. "The best thing about it is that Scott gets it," she added.

"So he knows you've been with other women?" I asked astonished.

"Oh hell yeah," she replied as she stood up. "He knows I love him and he's my man. But he also understands that a woman can give me something he can't, so he understands," she stood there smiling at me for a moment. "I'll be right back," she said as she turned and exited the room.

I laid there stunned and trying to take it all in. I'd just had my first sexual experience, and it was with another woman. But the weird thing was that as it was happening, I never got the feeling that I was gay or bi. Just a horny girl getting off with a horny woman.

The other thing about it - and I had to chuckle - was that it was Mr. Taylor who got my juices going, but I ended up doing it with his wife. How weird was that?

Bev was back in short order with our topped up wine glasses. She sat on the side of the bed I was on and presented mine to me.

"Thanks," I said with a smile as we clinked glasses.

"So are you sure you're okay?" she asked me quietly as she eyed me.

"Bev I am more than okay," I said in a sultry voice.

"Good," she replied as she placed her wine glass on the nightstand and then took mine from me and placed it there as well. "Because this party is only getting started," she said with a devious grin.

She slid onto the bed and eased her face between my legs and wrapped her arms around my thighs. She slid her tongue over my bare pussy and I shivered with delight as the sensation of it.

I moaned with pleasure as she worked her tongue up and down over my lips before darting her tongue inside me and swirling it around. GOD! This felt SO good!

Bev continued to dart her tongue in and out of my pussy as she willingly lapped up every ounce of moisture that I produced, as well as the burst of cum that I spewed forth as she made me cum.

I arched my back and dug my hands into her hair and moaned my approval of everything she was doing to me.

She unhooked one of her arms from my leg and then eased two fingers up inside me as her tongue went to work on my clit. I felt myself spurt even more slick goo forth as she made me cum over and over again.

Bev brought me to one last mind-blowing orgasm and I swear I must have spewed a pint of cum all over of her hands. It was that intense!

She raised her head from between my legs and eyed me with a delicious smile. My hands, which had been on the back of her head slid down her arms and caressed them gently.

"Damn," she breathed heavily as she eased herself over top of me, pausing to lick both of my nipples. "You cum lots and you taste great!"

I didn't have any words to respond, so I just leaned up and kissed her on the lips.

******

We shared a cigarette and each had a few sips of wine. Then Bev asked if I was willing to reciprocate. I was only too happy to oblige.

GOD! It was so surreal! I couldn't believe how much I enjoyed having my mouth and tongue all over her pussy and clit. I couldn't believe how much I enjoyed tasting her juices. And her cum? OH MY GOD! It was WAY cool!

I felt so proud of myself as I made Bev cum over and over again considering this was my first time pleasuring a woman.

It made me feel even better that I was able to draw one last intense orgasm out of her as she had done to me. Man, did she cum huge on that one!

I crawled up and nestled into her embrace and we laid there in a sweaty mess of pleasure.

******

Bev and I ended up taking a shower together and playing with each other the whole time. We spent the entire night naked with each other. At times we'd sit and talk and at others we'd get back to pleasuring each other again.

About eleven pm, Bev called my mom and told her it was another late night and it would be best if I just crashed there.

"So," she smiled at me. "You're spending the night."

******

The next morning Bev and I had another shower after a wonderful night with each other. Afterwards I got dressed and she called a cab for me.

"Listen," she said as she gave me cash for the cab. "If you can, would you be willing to come over Friday evening? I've got a feeling Scott is just going to love you."

HOLY SHIT!!

******

On Monday at school I hooked up with Nicole for a smoke during lunch.

"So?" she asked. "Has the great 'baby-sitter gets to fuck the dad' thing come to fruition?"

"Not yet," I gave her a knowing smile. "But I did fuck the mom."

"No shit," Nicole seemed genuinely impressed. "Way to go!"

"Listen," I said as a took another puff of my smoke. "I've got a favor to ask."

"Name it," she replied.

"I've been invited over on Friday," said with a sly grin. "And, dad will be there."

"Oh holy fuck," she giggled loudly. "No way!"

I took a puff of my smoke and bobbed my eyebrows. "Way," I replied as I exhaled slowly.

"I gotcha," Nicole giggled. She dug into her bag and pulled out her phone without turning it on and placed it to her ear. "Yes Mrs. McGrath? Oh yeah, Jenny's here, she's just in the shower right now, can I have her call you back when she's done?" She laughed as she tossed her phone back into her bag.

"You've got it," I smiled at her. "I need an alibi."

"I hear ya," she chuckled as we both tossed our smokes to the ground and butted them out as the bell rang announcing afternoon classes were about to begin. "I needed some of my own," Nicole continued as we walked back into the school. "Otherwise I wouldn't be getting laid by a forty-four year old biker."

******

I was SO waiting for Friday to arrive, so naturally the week seemed to drag by. Tuesday dragged on FOREVER! Wednesday was a bit of a drag too. But during lunch I was having a smoke with Nicole when she asked me a very pointed question.

"I know you've never been with a guy, right?" she said flatly as she took a puff. "But have you at least used a dildo on yourself?"

"No," I replied with a shrug. "Why?"

"Because the first time it's gonna hurt," she replied matter-of-factly.

"Well I kinda know that," I said somewhat sheepishly. "But it gets better after, right?"

"Yeah," Nicole said nonchalantly. "But do you really want to go through having to deal with the pain of it on a night like you've got planned?"

I furrowed my brow as I thought about that. The truth of the matter is that I did not want to have to deal with that.

"Look," she said with a smile as she tossed her smoke to the ground and butted it out with her foot. "It'll be okay," she put her hand on my shoulder and leaned in to me a bit. "Can you come over to my place for a bit after school?"

"Um sure," I said as I tossed my smoke aside. "Why?"

"I'm gonna help you get ready for Friday," she said with a bit of an evil grin.

******

"Don't worry," Nicole said as she guided me into her home. "My mom won't be home before six," she added as she tossed her bag to the floor and headed to the kitchen.

It was a nice place - maybe not as nice my place, or the Taylors' but nice nonetheless. The cool thing about it was that it was only about four blocks from the Taylors' house.

"Do you want a pop?" Nicole called out as she opened the fridge.

"No thanks," I said politely as I placed my bag on the floor and took my shoes off and stood just off the living room.

Nicole emerged from the kitchen with a can of pop in her hand. "Fuck," she giggled. "Don't be so timid. Come on in!"

"Sorry," I smiled, a bit embarrassed. "I'm always a little nervous the first time I'm in somebody's house," I added as I walked into the living room.

"Oh really?" Nicole laughed. "After what you told me you did the first time you babysat for those people?"

I felt my face redden. "In my defense," I sighed. "I had been there for a few hours before that happened."

"Oh c'mon Jen," Nicole chided me. "Chill."

I took a deep breath and nodded.

"Okay, good," she said as she took a swig of her drink. "Now, first off. We can't smoke in the house."

"Got it," I nodded again.

"Good," she smiled at me. "Now, let's bust your hymen."

Nicole led me upstairs to her room. WOW! Was she a slob! There was clothes all over the place and the room was basically a disaster area.

As if she sensed my thoughts Nicole piped up immediately. "I know it's a mess," she sighed. "Please don't be judgmental."

I couldn't help but laugh.

Nicole shuffled over to her nightstand, and pulled open the drawer. "Here he is," she said proudly as she pulled out a dildo and showed it to me. "This is the guy who took my virginity!"

Holy shit! That thing looked huge!

I was amazed that Nicole seemed to be reading my expressions. "Don't worry," she said in a soothing voice. "I know it looks big, but I've got some KY in here too," she added as she turned back to the nightstand. "It'll help it slide in real nice."

I could feel myself tingling with both excitement and nervousness. "Okay," was all I finally muttered.

"Don't worry Jen," she said as she pulled the tube of KY out of the drawer. "It'll be fine."

"Okay," I said again but with more confidence this time as I accepted the dildo and tube of KY from her hands.

"I'll leave you to it," Nicole said as she gave my arm a rub.

"Oh you don't have to leave," I said in a very matter-of-fact tone as I made my way to the bed.

"You want me to watch?" she playfully chided me.

"I don't want to chicken out if it hurts too much," I replied flatly as I pulled my pants down. "And I know you won't let me get away with that."

"Fair enough," she chuckled. She headed over to her dresser and hopped up on to it in a seated position. "Jesus," she breathed. "You have a great ass!"

I chuckled as I stepped out of my pants and thong. "Thanks," I replied. "Even though I haven't seen your's naked, I think it's great too."

"Oh well thank you very much," she playfully replied. "Well? Get to it?"

I took a deep breath and picked up the dildo and the lube. "Do I just lube the dildo?" I asked completely in the dark about what I was about to do. "Or do I use some on myself too?"

Nicole placed her pop onto the dresser and hopped off it. "Here," she said with a smile. "Let me," she took the dildo and lube from me. "You really need to get the head slick for your first time," she explained. "But you also need to make sure you get his shaft coated. It sucks when you get him inside and then have him get stuck."

I nodded and smiled at the fact that she referred to her dildo as 'him'.

"How wet do you get?" Nicole asked me as she lubed up the dildo as I watched.

"Oh," I was taken a bit aback. "Pretty wet," I admitted.

"Okay good," she said as she finished lubing up the dildo. "You might want to play with yourself a bit and get the juices flowing. It'll help," she added with a smile as she tossed the tube aside and handed the dildo to me. "I can leave for that part if you want."

"No," I sighed. I stared at the dildo as it glistened with lube and I already felt myself getting a bit wet. "If you're going to be here when I say hello to your friend, you may as well stick around."

"Your call," she giggled as she headed back to the dresser and hopped back up onto it. "I gotta say Jen," she continued as she picked up her can of pop. "You are impressing the hell outta me."

"Thanks," I smiled at her as I eased myself onto the bed. I held the dildo in one hand and looked at it, as I placed my other hand over my bald pussy and began to rub.

Oh wow! I was already wet! I could feel it even before I parted my lips and eased a finger up inside myself. I dug my teeth into my lower lip and closed my eyes. I imagined Mr. Taylor and pretended it was his cock I was holding in my other hand. I thought back to my night with Mrs. Taylor and the incredible amounts of pleasure she brought me. As I eased my finger in and out of me I was soaking within an instant.

"Okay," I said with short breath. "Here we go."

I pulled my finger out of my pussy and guided the head of Nicole's dildo towards it. I hesitated for a moment, then pushed the head of it against my lips. I groaned a bit as I felt it pushing against me. I trembled with both anticipation and fear and I pushed it harder against me.

SHIT!

It slid up into me in an instant. I gasped loudly as I felt the head of the dildo inside me. I was breathing heavy and enjoying the sensation. I pushed a bit more and eased it up inside me a bit more.

Okay. Now it fucking hurt! My face grimaced with pain and I felt the urge to pull the damn thing out of me.

"Keep going," Nicole quietly urged me. "You're almost there."

I nodded but continued to wince with pain. I pushed it a bit further inside me. It was lubed up enough, and I was wet enough for it to continue moving forward, but FUCK! It hurt like hell!

I pulled it back a bit and took a breath then pushed it back up inside me. I opened my eyes a bit and glanced down. I flopped my head back onto the pillow in frustration as I saw that there was nowhere near as much of it inside me as I had thought. I pushed harder.

"Shit!" I cried out.

"Come on," Nicole urged me quietly. "You can do it."

"I don't think I can," I whimpered. I held the dildo in place and felt myself tensing up.

"Yes you can Jen," she said emphatically. "I know you can do this. I know you WANT this! Do you really want Friday to end up with you saying 'I can't do this'?"

I knew I didn't want that to happen. So I pressed on. I pushed the dildo against me and felt myself now biting into my lower lip so much I was afraid I was going to draw blood.

"Okay," Nicole finally sighed. "You're tensing up way too much," I heard her hop of the dresser.

I opened my eyes and saw her approach the bed. "I can get this," I whimpered at her.

"Not right now you ain't," she replied matter-of-factly. "C'mere, gimme," she reached down and took the dildo from my hand and pulled what little of it that was inside of me out.

I sighed with regret and rubbed a hand over my face. "Shit," I moaned.

"Don't worry," she said in a soothing voice. "Who knows? Maybe it's me being here that's fucking you up. But you need to relax."

I lifted my hand off my face and looked at her and nodded. "You're right," I breathed.

"Close your eyes," Nicole said to me softly.

I eyed her curiously for a moment then did as I was told.

"Now," she continued in a soft voice as she traced the dildo up and down my thighs. "Think about what you and that hot mom did."

She guided the dildo over my pussy and I quivered with delight recalling my time with Mrs. Taylor.

Nicole brushed my thighs with the dildo again. "Now," she practically hissed at me. "Imagine dad, with his cock outside your pussy," she pressed the dildo against me again.

I immediately envisaged Mr. Taylor's handsome face and imagined it was his cock I was feeling against me. I wrested the dildo from Nicole's hands and shoved it up inside me.

"OW! GODDAMMIT!" I shrieked. Whatever I'd just done had hurt like hell.

I was about to pull the dildo out of me but Nicole kept me from doing so.

"Keep going," she hissed. "You're there!"

I felt my face wince again as I drove my teeth into my lower lip. But I did as Nicole said. I didn't have much choice since she was holding her hand over mine and keeping the dildo in place.

I felt myself quivering as I held the dildo inside me. I knew I had to go deeper to finish things off but I couldn't find it within myself to do it.

Fortunately Nicole was there and she must have sensed what I was going through. Because she went from holding my hand in place to pushing against it and forcing the dildo further up inside me.

"Oh fuck!" I yelled loudly. For a moment it hurt worse than anything I could imagine.

Then? OH MY GOD!! I arched my back and felt myself gush cum all over Nicole's dildo.

"Oh holy fuck!" I breathed heavily.

"Hymen busted," Nicole giggled. "Now the pleasure begins."

She continued to push her dildo in and out of me and I came over and over again. Oh my god! This was fucking magical!

Without even realizing it I hooked my leg around Nicole as she continued to work my pussy with her dildo. I even felt her reach down and massage the leg that was wrapped around her.

******

"I thought you were going to kiss me," Nicole chuckled as we were out back having a cigarette.

"I was pretty close to it," I chuckled back as I took a puff of my smoke. "God that was amazing!"

"Yeah," Nicole replied as she blew some smoke out of her mouth. "My guy does good work doesn't he?"

"No kidding," I admitted. "But seriously Nicole," I added. "Thanks for your help."

She gave me a wave of her hand. "You'd have gotten it eventually," she said.

"Still," I sighed as I took another puff of my smoke. "I'd have hated to be over at the Taylors' and not be able to have him fuck me," I shook my head.

"Oh hell yes you would have," she chided me. "It's way different doing it real than with a dildo," she said as she butted her cigarette out. "Real? It would happen. No doubt."

"I guess you're right," I shrugged as I butted my smoke out too.

"Damn straight," Nicole said as she slid open the sliding door that lead back into the kitchen. "As soon as I told you to imagine those two, you were right into it.":

******

It was Thursday.

"Hey mom," I asked as we were in the kitchen getting dinner ready. "Is it okay if I crash at Nicole's place tomorrow?"

"Nicole?" my mom asked as she drained some noodles in the sink. "Have I met her?"

"Um, no," I replied. "She has an after school job so she's not been over here," I lied. "But I know I've told you about her."

My mother's brow furrowed. "Okay," she said. "I don't recall. Do I know her parents?"

"It's just her mom," I replied as I finished tossing salad. "They live a few blocks from the Taylors"

"Well," my mom said. "If her mother is okay with it, then I guess it's okay."

******

Later that evening the phone rang. My mom answered and beckoned me over. "It's for you," she said holding out the receiver. "It's Mrs. Taylor."

I hoped I wasn't blushing as I took the phone from my mother. "Hi Bev," I said. "What's up?"

"I'm looking forward to having a wild time with you and my husband tomorrow night," came the sultry response. "I hope you're still willing."

"I am," I smiled as I watched my mom sit down on the sofa.

"Good," I heard her exhale and knew she was smoking. At that moment I wanted to light up myself. "It took a little convincing but Scott is totally into it," she added. "Do you have a cover story? We might want you to spend the night."

"Oh yeah," I replied as I twisted the phone cord. I swear my pussy was soaking wet! "I'm crashing at a friend's place on Friday night."

"Good girl," she breathed back through the phone. "Now put your mother on the phone okay?"

"Sure thing," I smiled broadly. "Mom?" I called out. "Mrs. Taylor wants to talk to you," I held out the receiver for her.

My mom took the phone from me and I made my way to the living room as she chatted with Mrs. Taylor.

"Oh really?" my Mom said. "Well I don't have a problem with it," she added.