My First Sexual Encounter – Babysitter I

My first sexual encounters started at a very young age. I had a babysitter with 3 older brothers-the oldest, Dennis, would “fill in” when she wasn’t available and he was in his late 20’s. Dennis was a very shy and gentle man and he always found ways to be alone with me, our “special time”. At night, he would personally tuck ME in, not like my brother and sister who he would send off to bed on their own.
He would quietly stand by the door and watch me change out of my play clothes and into my long white nightgown–glancing at me over his shoulder. Then, when I would climb into bed, he would close the door and turn off the lights so only the moonlight shined  in through the window across my bed. Dennis would then offer to gently rub my back so I could fall asleep easier. I remember his strong, big, gentle hands lightly lifting my nightgown to expose my pink panties and bare back, then he would gently caress my shoulders, down my spine, down to my lower back and run his fingertips along the edge of my underwear and making their way slowly back up the side of my body.

Sometimes I would feel the slightest graze of a fingertip brush over my prepubescent breasts and it would cause goosebumps to jump all over my body. He would gently coo in my ear how soft my skin was and asked if I liked the way he touched me (and I did). He would then move my underwear slowly down an inch at a time, explaining that I would enjoy it more if it was skin to skin without the fabric. I sleepily agreed and then I could feel his hand caressing my petite little cheeks and adding a little squeeze now and then as he cupped the fullest part. One night as we began our usual bedtime routine and I was changing, he suggested that I just leave my panties off–as I lay down on my stomach and he lifted my nightgown—this time he stayed focused on my ass–caressing, kneeding and rubbing–I could feel the urgency in his touch and I was surprised that I was getting very damp between my legs–I was glad for only the moonlight from outside so he wouldn’t see how deeply I was blushing. Then he ran his fingers down between the crack of my cheeks slowly and continued down grazing across the plump lips of my little pussy causing me to arch my back and spread my legs a little wider—he seemed pleased and asked if I liked how he was making me feel–I mumbled out that I did and agreed to let him continue.

This time he spread my legs even further and gently began stroking my lips, he placed his other hand under my stomach and lifted my hips in the air. While holding his hand and pressing on my pubic area he placed a finger slightly in between my pussy lips-stroking and spreading my wetness. Then slowly he began to edge that finger into my tight little pussy and I moaned deeply into my pillow. The feeling was like nothing I had ever experienced–he began sliding in and out of my pussy, going a little deeper each time and pressing on my pubic area a little harder with each deep stroke. He was breathing heavily and whispered in my ear how beautiful I was and that he  wanted me to relax and let go–As he inserted a second finger inside me sliding it in deeper and faster, pushing and working my hips back against his fingers I felt a wave of glory and a flush of heat spread over my body and my legs began to tremble as he spoke those words in my ear…”let go” and everything inside me gushed out between my legs onto his fingers and hand soaking the sheet beneath me. As I lay there–legs trembling and heart pounding-I fell asleep dreaming of our next encounter.