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Lisa’s Confession Sessions Ch 2 Rubbing and
Gwen stayed in my bed and pretty soon began to take things in a new direction.
I wanted to learn, no I’d pleaded to learn how to touch myself as I had found her doing. Gwen had finally obliged me and then gave me my first orgasms and then had me taste myself and her.
Gwen was beautiful and at that moment, on my bed, in the low light of the room, she looked like a young Victoria’s Secret’s model. Her Mexican and white features were dreamy. Her bra and panties were actually a smaller Victoria’s Secrets set and were shiny around her cup and then lacy at the top. Likewise, her panties had a shiny satin-lycra forming the body of the panty’s crotch and were trimmed elegantly with lace on both sides.
Gwen reached down and pulled my hand to her crotch while her other hand pulled the cups downward and off her breasts and then torqued the panty-crotch away from her pussy. Gwen placed my hand on her ‘outty’, I soon leaned was called a ‘clit’, and began gently rubbing my fingertips around in a circle.
I was amazed at how much larger hers was than mine and reached down to touch mine in comparison. I was shocked, because mine was far larger than ever before. I was swollen and briefly wondered how I would explain this radical change to my mom.
“That’s it, nice and gentle…little circles around my clitty…be nice and rub my hot little clit…” Gwen moaned. She still had one leg off the bed, but was now lifting her body slightly off the bed. Her head leaned back and away and she breathed heavily. After about twenty or thirty little gentle circles she took my fingers away and moved them downward to her tight flapped lips and then upward and inside her. Then she took her other hand and began rubbing her ‘clit’. She became very intense with her breathing and then, l felt her, well, her hole, compress around my fingers and then the convulsions occurred in her, just as they had in me.
Gwen screamed, “Hawwwh!! Ohhhhh! Fuck!!! AWWWWhhhhh!” I was so scared and surprised that I almost dived off the bed. Gwen’s grip held me in place and I just went with it.
Over the next two hours Gwen and I masturbated. She taught me all she knew. I even went into the guest bedroom where I had discovered her masturbating just after bedtime and watched myself cum. The last thing we did that night was to combine masturbation of each other with a kiss. Gwen taught me how to kiss and probe with my tongue. This added a new level of sensuality to the process. Gwen also taught me what everything was called, my ‘outty’ was actually a clit, my warm crotch hole was actually a vagina, a pussy, or if I wanted to be really naughty, a cunt.
The only reason we stopped was because we heard my mom pull up in the driveway after getting home from the end of her 12 hour shift at the hospital.
Every time mom mentioned Gwen as a babysitter two things happened. I felt a swelling begin in my crotch and a pulse of erotic energy, and a struggle by me to hide those reactions from my mom.
Of course, when dad was in town for his work it felt like I never saw Gwen. I was so excited when dad told me that he was going to take mom on a date just before he headed back to Alaska. I knew that what he really meant was that he was going to take my mother to a nice resort hotel, wine and dine her, and then, without graphic in my own mind, I knew he was going to fuck her brains out.
I became excited because I knew Gwen and I would be able to play and experiment and who knows what. I knew I would cum – a lot – while she was baby sitting.
I was becoming quite capable of pleasing myself. I had even pleased myself as a birthday present, a full decade, and so loved the orgasms. I would come home from school, or after-school gymnastics class and make myself shake and sweat daily.
Roughly six months after my birthday my dad told mom and I that he was getting a promotion and would be gone for three months. Mom was upset until dad explained how much money he would make and that was a clear path to management. A week later, we all went to a family event put on by his company and met dad’s boss.
I will call him Karl (not his real name of course). He was of German descent and was very strong looking, with blonde hair and blue eyes. He wasn’t taller than my dad, but he was about ten years older than my dad’s young-looking age of 43. Apparently the party was to recognize my dad’s promotion and a new project for the oil company in Alaska. I decided that I kind of liked my dan’s boss after he played tag-your-it with me out back. It was a very happy event, but thinking back on it later, I realize now that Karl promoted my dad to fuck my mom.
“Wait, what does this have to do with Gwen?” Dr. Heard asked me.
“I am about to get there. You wanted me to do this in order right?”
“Yes, but I need to know more about your relations with Gwen the babysitter.”
I exhaled my irritation and relied, “Well, the short version is she had me suck off her boyfriend…do you want to know how it happened?”
“Yes! Uh, I mean, of course, I must know,” Dr. Heard blurted out.
Dad took mom to a resort for a Friday and Saturday night. Gwen was hired on to take care of me from six PM on Friday until they got back Sunday afternoon. By now, Gwen and I had done mostly everything possible, except penetration of me. I had used a sex toy – a dildo – on her dozens of times, but still had nothing inside me except for fingers, and only my fingers, almost never hers. Gwen refused to let me “take it inside” because of my small size. The dildo was a hearty and thick eight inches and totally blocked off my throat when Gwen forced it in my mouth.
Gwen was dropped off by a college friend of her brother’s at six. Gwen’s brother had just left for the marines and his best friend was watching over Gwen to keep her out of trouble. Dad and mom left a few minutes later.
By six-thirty I was on my knees eating out Gwen’s cunt. By about six-thirty five, Gwen had cum in my mouth, we’d kissed and she was having me straddle and ride her mouth as she laid beneath me on the floor. We paused around eight to have some pizza and then resumed while we watched a horror flick on TV. We slept a few hours and then I was woken by her eating me out. I reciprocated and on and on we went until morning. We slept the morning away and were woken by mom’s call to make sure we were ok.
We went to the park and finger fucked in the bathroom. We went to the mall and bought sexy underwear, which we then wore in the house the rest of the day. About seven Gwen came around the corner and she was dressed, while I was still in my naughty black bra and panties.
“You are so cute. I love your strawberry blonde hair, but I bet you would be really cute as a red-head…you certainly have the skin for it.”
“Thanks, maybe for my birthday I will ask my mom. Why are you dressed?” I asked.
“So, I need you to be cool about something. My boyfriend is coming over in a few minutes. If you are ok with it, he and I are going to play around in the guest room.”
“Uhmm, what to you mean? Is he going to???”
“Yes. He is going to fuck me.”
“Oh? That’s all you say?” Gwen asked surprised.
“Well, I mean he is your boyfriend. Can I watch?”
“Well, I don’t really think that would be a good idea.”
“Aw, come on. I haven’t ever sent eh real thing. Your in my house. I wanna watch,” I protested.
“I am just, well this is so dangerous. Nobody knows what we do together and it can never be known. I just don’t want you to get in trouble.”
“Why would I get in trouble?”
Gwen told a white lie, but very convincingly, “Well, girls can sometimes be jailed for watching things they are not supposed to. I know, after all we have done, this is probably a shock, but since I have been protecting you and keeping our playtime a secret, I just want you to know that jail isn’t worth it.”
“Oh.” I accepted the lie, but didn’t care. This was another big moment for me. Though it was predicated on a lie, I knew I wanted to watch, hell, maybe even take part in some way.
Gwen an I eventually arrived at an agreement that I could watch, but could not touch unless Gwen said so, and under no circumstances could I be touched by Ricky, her boyfriend.
An hour later Gwen, wearing the clothes we wore to the mall, but substantially more makeup, especially on her lips and eyes, pranced downstairs and welcomed Ricky. He had been the friend that had dropped her off.
I was introduced and then Gwen gave me a juice and the TV remote while she took him upstairs. Gwen knew that was all for show and that a minute after they closed the door I would be in my hiding place in the guest bathroom watching in the dark though the open door.
I snuck into the bathroom and saw Gwen on her knees sucking off Ricky. His athletic frame was model-like. He had no fat, but did have muscle and what I later learned was a really nice sized cock – about eight inches, and clean cut. Gwen sucked him and then stood, turned and dropped her shorts. She leaned toward the bathroom door and placed her hands alongside the huge floor mirror next to the door. Ricky reached around her waits and grabbed Gwen’s pussy and also shot a hand up her shirt to massage her bra-covered “A-cup” breast.
He penetrated her from behind. He was lifting her off the floor every time he pumped into her. All of a sudden, Gwen began to orgasm. I knew her well enough to tell when she came, and this was an amazing orgasm.
Then, as she came a second time, Ricky also reached the threshold and came. As he did, he pounded her so hard that her head slammed into the wall next to the mirror and.
“Owe! Ahhh, hahhh, uhhhh…” Gwen muttered as Ricky finished using her.
The whole thing had taken only about five minutes or so, but I could tell by Gwen’s expression, that it had been worth every second. Ricky pulled away from her and Gwen pivoted and dropped to her knees. Gwen tugged at the top of the condom while pulling it free with her other hand. I saw how full, or empty rather, it was, but Gwen smiled and gleefully up-ended the condom and drained it into her mouth with a wicked smile.
Ricky watched and smiled, “Fuck, that is hot…nasty girl…”
Gwen licked her lips and smiled. Then she said, “Yeah, you should see what my brother and I used to do…”
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