Babysitting Bliss

Scott had completely forgotten about an office function he was obliged to attend on Saturday night and desperately needed a babysitter for his niece & nephew that he was caring for that weekend.

Lucky for him, I lived downstairs and my mother was always offering my services around the building as a babysitter.

I hadn’t babysat for many people in the building, usually working for friends of my mom who lived elsewhere, but it seemed like easy work. Put the kids to bed early, watch some movies, raid a fridge... and just generally relax.

Scott was a couple of years older than me, ok… more than a couple. I was only 19 and he was 27, but it didn’t seem like much of a difference. On more than one occasion I caught him stealing a glance at me, but never once did I think things would progress as quickly as they did between us.

Whenever he saw me in the hallways, he was always very sweet and talkative. Scott was always interested in how college was going, and had even offered to help me on a few occasions.

Anyways, back to tonight.

My plan for a relaxing evening was cut short when I realized the kids were hell on wheels. It took all my energy to finally manage to get these kids into bed and asleep.

When it finally happened at about 10:30pm, I was so tired, that I just didn’t think of what I was doing. Scott’s couch isn’t comfortable at all; in fact, he could really use a new one, so I crawled into his room and curled up on his bed to sleep for a bit.

I kept the door open, so that I could hear the kids if they woke up. I pulled my jeans off and threw my socks into a pile. I didn’t even think of Scott as I did this. I was wearing a long t-shirt and pulled it down over my thighs as I leaned back onto the bed, subconsciously grabbing his pillow, wrapping my arms around it and falling into a deep sleep.

When I awoke almost 2 hours later, Scott was sitting on the edge of the bed. I had no idea how long he had been watching me, but I could see that he hadn’t just sat down.

“I’m sorry to have woken you up, I just got home” he lied, as I suddenly realized that I was half-dressed and pulled his blankets close over my legs.

“Oh, no” I stammered, “I should be the one apologizing, I shouldn’t have gotten so comfortable in your bed, Scott.” I thought about getting up out of his bed, but found myself in a very awkward situation, as I didn’t want to be half naked in front of him, but couldn’t stay in his bed.

“If your tired, feel free to stay here in my bed…” he stumbled through the sentence and I could tell he was getting nervous. “I can call your mom and say you fell asleep, and you can leave in the morning.”

It sounded like a great offer. I was already in bed, and staying the night would get rid of the awkwardness of having to get up and get dressed. I could do it in the privacy of his room in the morning before leaving. I nodded in agreement and he left the room to call my mom.

“Well, I think I woke her up, but she was fine with everything,” said Scott as he strolled back into the room and began to undress. “I hope you don’t mind if I take off my shirt and gather a few things before I head into the living room to sleep, do you Jenn?” I didn’t know what to say at first, but then he slowly revealed his tight stomach muscles and I felt a strange feeling within me.

“No, not at all. Here would you like your pillow back?” I offered as I stretched my arm and presented it back to him.

“No thanks, I have a spare in my linen closet” he stated as he slowly undid his pants, slipping them off onto the floor to reveal his boxer shorts. “So, are you dating anyone at school?” he questioned.

I sat up straight in bed and nodded my head back and forth. He seemed surprised by my answer and his questioning started to excite me. Scott started asking questions about the guys at school and suggested that maybe they were intimidated by such a beautiful girl, which was why I hadn’t been dating. He made me blush and he knew it.He asked if I had been kissed and if I enjoyed it.

“I have been kissed a lot…” I said. “Most guys my age all want a lot more than just kissing.” I pulled his blanket closer to my body, as I noticed I was gradually getting more excited.

“And you don’t want more?” he questioned.

“Well, I do. Just not from them. I want someone with experience.” I said. “Someone like you.”

At first I regretted what I had just said. Then I realized how much I wanted him, so my regrets just disappeared, and instead I hoped he wanted me too!

He sat on the edge of the bed, close to me and slowly leaned in. My eyes instinctively closed and I felt his warm lips press against mine. My body seemed to go limp at first as both our mouths impulsively opened to find probing tongues waiting to explore each other.

I sighed gently as I felt Scott’s hand reach around to cup my head and pull me closer to him. He leaned into me, pressing his lips against the side of my neck and taking in my scent. With each move he made, I was getting more aroused. I could easily see the excitement within his shorts and this thrilled me more.

“I shouldn’t be doing this... we shouldn’t be doing this” he exclaimed as he leaned back. “You’re the babysitter… and I’m well… I’m a lot older than you.” He seemed nervous all of a sudden and it made me feel guilty.

“Don’t apologize,” I answered. “I want you”

He reached around my waist and pulled me tightly to him. Scott leaned me back onto the bed and had me spread my legs apart slowly. He ran his hands lightly over my inner thighs and I felt a slight twinge in my body.

“Have you ever had sex before?” Scott asked quizzically as he continued to massage my legs tenderly. I nodded my head in disagreement as I felt his hands move higher up my inner thighs. “Would you like to?” he finished.

I was caught off guard, but the feeling within me was so overpowering that I yelped a small “yes” as he leaned forward and kissed me. His hand then cupped my covered pussy and rubbed oh so gently. I could feel his hand tugging at my panties gently as he slowly moved them to one side of my tender pussy lips. All of a sudden, I felt a finger slowly run up the inside of my lips and I gasped.

Scott pulled me over to the edge of the bed, so that my legs were resting on his shoulder as he was on his knees on the floor. My wet hole was right in front of his face and I didn’t feel awkward any more. I felt at home with him and it excited me. His fingers began at first, slowly tracing their way around my lips, but never entering me. Then I felt the strangeness of his tongue licking my hard clit. I panted in exhilaration as he stuck his tongue into my tight, wet hole.

With every move he made, I got more excited. I had never felt the way I was feeling with Scott at that moment. He peeled my panties off my body and slipped one hand up between my tender pussy lips, rubbing gingerly, as his lips closed over my hard clit. He began sucking it hard between his lips then Scott put one finger against my slit, spreading my lips open before pushing his finger into my soaking wet entrance. My pussy grabbed his finger, taking it deeper into my tight cunt until it was buried inside me tightly, like a vacuum.

I slowly pulled my t-shirt off and pulled my bra down to reveal my overflowing breasts with hard nipples. Scott didn’t even pay attention; he was too focused at the job at hand. He proceeded to bend his finger slightly as he continued to suck on my clit. He could hear my panting and as he opened his eyes, he saw my breasts rising and falling as my anticipation grew.

He knew he was taking a chance, but he wanted to taste more of that sweet cum on his tongue; he wanted to be the one to drive me over the edge for the first time, the second time and the third time. Scott felt my pussy gripping his finger and slid it a little deeper into my tight hole. I was in heaven and I’m pretty sure he was too. He wanted me just as much as I wanted him.

---------------------------------------------

I couldn’t believe that this was happening to me. I had seen Jenn many times in the hallway in the building and often masturbated while thinking of fucking her body, but I never thought it would ever happen.

My finger was soaking wet from drilling her slit for the past few minutes. I knew she would come any moment and I wanted to make sure she came once without penetration and had her exactly where I wanted her; begging for more. She arched her back slowly and I reach my free hand under her ass and began to circle her tight puckered asshole with one finger. If I had my way, I’d be penetrating every one of her holes tonight.

Jenn moaned loudly and I whispered to her to try and contain herself. I had just remembered that the kids were still fast asleep down the hall and I wanted to keep it that way. I pulled my finger out of her tight pussy and lifted it to her lips. This would definitely quiet her, I thought, as I plunged my wet fingers into her mouth for her to suck on. She sucked feverishly as though this was her last meal and would never be satisfied again. While she sucked, I leaned my face down and proceeded to lick her gently from her tight asshole to her sopping wet pussy.

As my tongue darted in and out of her hot wet hole, I placed one of my fingers on her clit and began to rub it slowly. I could tell by her low moaning that she was going to explode soon, so I would alternate my motions by placing my fingers in her pussy and licking her clit feverishly. When I thought she couldn’t take any more, I bit down on her clit gently and plunged my finger deep inside her. Her tight pussy clamped down on my finger and she came harder than anyone else I have ever fucked.

I pushed her body onto the bed and lied down on top of her, kissing her lips gently and running my hands all over her body. My hips were equal with hers at this point, and she could feel my hard cock between her legs. I sat up on my knees and took her legs and spread them as wide as they would go, bending them at the knees, so I had a great view of her sweet, wet pussy.

I grabbed her hips and pulled her body closer to mine, making sure my cock was right in line with her open hole. My cock was extremely hard and eager for her pussy to envelope it, so I leaned forward into her and placed my head right at the entrance to her sopping wet pussy. Jenn’s mouth opened and I could tell she was about to say something, but before she knew it, I had thrust my hard cock deep inside her virgin pussy and she was yelling loudly.

At first it sounded like yells of pain, and then slowly, they became moans of sheer pleasure as I continued to ram my hard cock inside her. My hands reached up and grabbed a hold of her breasts, pinching her nipples as I kept fucking her. She was so eager to be fucked, and I was in heaven with my cock buried up to the hilt in her wet box.

Keeping her tightly around my cock, I grabbed her waist and rolled her over onto her front. At first, I pushed her chest down to the bed so her ass was high in the air, and I had a nice view of her tight asshole while I fucked her, and then slowly, I got her up onto all fours. My hands reached down under her body and pinched her nipples more, while her moans became more frequent. I was not in any hurry to make her cum again, so I pulled out of her pussy and put my finger deep inside her, getting it covered in her sweet juices.

I was tempted to lick them off, just so I could taste her sweet nectar again, but instead I pushed her chest back onto the bed, and placed my wet finger right at the entrance to her tight ass. I could tell she was hesitant at this idea, but I knew she would go along with it once she knew how fabulous it felt.

I continued to rim her ass with my wet finger, and then brought my tongue down and began licking all over, and plunging it gently into her tight ass. Jenn was doing a pretty good job of loosing up her ass, so I decided to bring her back to the brink of ecstasy before I plunged my cock into her tight ass and gave her the fucking of a lifetime.

With her face down on the bed, I stuck my hard cock back into her wet hole and finger her ass with one hand, and fingered her clit with another. She was writhing pretty fast after only a moment of pleasuring her; I pulled my hard cock out, and placed it right at the entrance of her tight ass. I could tell by the look on her face that she was worried it would hurt, but at this point I didn’t care.

As my cock began to work it’s way into her tight ass, she was reluctant and her ass tightened up. I needed her to relax so that I could fill up her tight ass, so I placed 1 finger on her hard clit and began to rub it. She relaxed very quickly at this point and slowly I was able to slide my entire cock into her tight virgin ass.

I worked my cock in and out of her ass very slowly at first, then finally picking up the pace as I realized what I was doing. I was finally realizing my fantasy, and if I had my way, she was going to turn into my personal slut. I grabbed her auburn hair and pulled her back towards me as I plunged deeper into her ass. Jenn pleaded with me to fuck her, and I wasn’t about to stop, but then I realized that I was on the verge of cumming.

I pulled out of Jenn’s ass and rolled her over onto her back. I placed my cock just above her mouth and instructed her to suck it, offering advice on how best to do this, as she was obviously inexperienced. After 2 minutes, she had my cock deep in her throat and I was moaning in pleasure, as I knew my explosion was imminent.

I pulled my hard cock out of her mouth and stroked it once until I came all over her luscious breasts and face. I think this surprised her, but she seemed to enjoy as she began to rub all my juice into her skin. We lay down on my bed together and curled up in the blankets, our arms wrapped around one another. I knew this was not going to be our last time, but certainly was a memorable first time.