Memories Of Our Babysitter Ch. 06

When I gauged that her arousal state was building back up again, and she was making more quiet sighing sounds, I gently slid one finger inside her a short way and let her get used to that before adding a second. She made more of a groan when she felt my two fingers moving inside her.

She was very tight, and I wondered how far I might get with my cock before it became too uncomfortable for her.

"Mmm, that feels good already, just like last time," she whispered.

I moved my fingers slowly in and out, gradually lubricating the inside of her pussy lips as her juices began to flow, until I felt that she might be ready.

"I'm just going to slide my cock up and down, so it gets a bit more slippery," I said, taking my fingers out and using them to hold my cock against her slit.

Using my fingers to steer it and my hips to move it, I began to slide my cock up between her wet labia, parting them and letting them slide back until I could see that my condom covered cock was slick with her secretions.

She seemed to like this almost as much as my fingers and let out a few moans of appreciation, especially when I deliberately let the tip rub against her clit.

"Is that your cock I can feel Pete?" she asked, her voice sexily breathy.

"Yes, does it feel ok?"

"More than 'ok', I think I could just put up with that all night, it feels so good."

"We could just stop at this," I said, wondering if that was what she meant really.

"No, I have this urge now to feel what it is really like, can we try it," she said, "I think I'm ready."

"I'll go slowly, just say if you want to stop." I said, excited myself at how close we were to being joined in the most intimate way.

"I can feel it there," she said, as I moved the tip of my cock round where I could see her pink entrance.

I pressed forwards, nudging the tip of my cock against her, seeing part of it opening her up. She flinched when she felt it but didn't say or do anything.

I held her slightly open with my fingers and pushed a little harder, She was tight, but I thought that if I could get the head inside her, and let her become comfortable with it, the rest would follow. However, the harder I pressed, even with the lubrication, the more it seemed to be resisting my penetration. It seemed as though her outer muscles had contracted, perhaps though nervousness, and were preventing my entry.

"I can't feel anything new, just like... pressure... you're not in yet, are you? Am I too small?" she said, sounding almost sad.

"No, it's ok, I just don't want to hurt you, but I may have to push a little harder, is that ok?"

"Try, I'll tell you if it's too much."

I pressed harder and I could see her entrance starting to stretch around the head of my cock further. I was at the point of thinking perhaps tonight wasn't the night, when I felt more of a movement and with a final push, the head popped through, and I lost sight of it inside her.

"Oh, Lord, stop," she said, loudly, "now I can feel something new, whew, don't move for a minute."

I stayed as I was, looking down, seeing the erotic scene of my cock between her young pussy lips, the fine, blonde. downy, pubic hairs surrounding it. My cock was definitely inside Cass' sister, even if it was just the head for now.

I stroked my hands up and over her breasts, toying with her nipples, giving her all the time she wanted.

It seemed longer but was probably only a minute or so at the most.

"Try a bit more now Pete," she whispered.

"You're sure?"

"Yes, it was a shock at first feeling stretched so wide suddenly, but I'm ok, I want to see if I can take more."

I pressed forwards, and now that the initial resistance had been overcome, a little more of my cock slid inside her.

"Hold it there for a moment, wow, it feels different to any of the other things," she said, "much bigger too."

I gently grazed her clit with my finger, hoping that sensation would take her focus away from the stretching she was feeling.

"Ohhh, mmmmm," she mumbled, so I guessed it was having some effect.

"Do you want to stop, now that you have felt it," I asked, hoping she wouldn't say yes.

"I think I can take more now, just keep going slowly Pete, please." she gasped, her breathing even faster than it was.

Moving my hands up the outside of her thighs to her hips, I held her there to support her and moved my hips slowly forwards, half inch at a time, seeing my cock sliding gently into her tight pussy. I kept the pace deliberately very slow until I felt my pubic hair just touching hers and with a final minute move forwards, our pubic bones met, and I was fully inside her.

"Oh God, I can feel you deep in me now, I feel just full of you," she said, almost as though she never expected it to happen.

I contracted my cock muscles so it twitched inside her.

"Ahh, I felt that, did you just squirt?" she asked.

"No, what you felt was it just twitching inside you," I answered.

"Ohh, it felt sort of funny, but nice sort of funny...do it again."

I did it a few times and I saw a slight grin on her face each time.

"I had no idea it would feel like this, but...will you tell me something honestly?"

"Of course."

"Do I feel... I mean does it feel ok for you,...like with other girls, I meant." she asked, almost shyly.

"It feels amazing," I said truthfully. "You are amazing and very sexy. Don't worry about things like that, as long as you are enjoying the feelings and sensations, that's all that matters." I said.

I saw with some alarm, a tear run from one of her eyes.

"Are you ok Helen, am I hurting you? Do you want me to take it out?" I said, worried for her

"No, no, sorry about that," she replied wiping the tear with a finger, "don't take it out, I am enjoying feeling it so deep inside me, but I feel a bit emotional at what you just said, and that you helped me be able to do this for the first time. It makes me feel more...ummmm... I don't know, just more confident I suppose, I'm not sure how to explain it."

"Well, I meant it, you are amazing."

"You'll make me cry if you continue saying soppy things like that," she said, a tearful smile on her face, "how about we try moving a bit so I can see how that feels?"

I had no idea that, unlike her sister, she would be emotional about it. I guess I should have felt bad about it, except she seemed happy that she had done it, and wanted to carry on. I had never had this sort of conversation with a girl while my cock was balls deep inside her for the first time.

I slowly pulled out just a couple of inches then slid back in to get her used to the movement and friction. Then I built up slowly to longer strokes, until after a few minutes, I was only leaving the head inside her each time. The trouble was, she was so tight, that being able to see my cock going in and out of her pussy as well as feel her tight walls around me, were giving me the most fantastic sensations and I was sure it would take me to the edge fairly quickly.

"Oh God that's amazing," she gasped, as I moved a bit faster and felt her trying to move her hips up to meet me, "ohhh, mmmmmm."

Now that she was pushing up to me, I didn't need to hold her hips anymore, so to try to make her come quicker before I totally blew my own load, I used the thumb of one hand to gently rub her clit in time to our thrusting, and the fingers of the other hand to tease one of her nipples.

That seemed to be having the desired effect, as the thrusting became more powerful, and I felt her legs trembling against my hips as she strained.

She was no longer the shy, inhibited girl of earlier, now she was sparing nothing to climb up towards her own release. The movements she was making, and the continued sight of my cock sliding in and out of her, was taking me very close, but I desperately wanted her to come, with me inside her, for her first time.

"Pete, Pete, ohhhhhhh," she started, but then made almost a continuous 'AAaiiieeeee' sound, only interrupted when she took a breath.

I knew she was about to have a major orgasm and that did it for me.

I let nature take its course and the familiar feeling starting somewhere deep inside me, streaked up through my balls, and up my cock, culminating in the release of jets of cum into the condom. I pushed my hips as far forwards as I could, burying my cock deep inside her. At the same time, I felt Helen's insides sort of contract around my cock and watched the muscles across her taut stomach ripple as her climax began to roll through her.

"Oh my God, Oh my God...," she started repeating, in a breathless voice, at the same time gripping the edge of the sofa with whitened knuckles, her head rolled from side to side with her eyes screwed tightly shut.

I kept thrusting with her until she gradually slowed down and stopped altogether. She raised her hand and pressed my fingers away from her clit, as I assumed it had become too sensitive for it to be touched for now, but I slowly and gently I continued to move my cock in and out the full length, as little jerks and contractions continued to pass through her body.

Eventually she put her hand against my stomach to get me to stop moving, my cock still about halfway inside her.

She slowly opened her eyes and looked at me.

"Phew, wow," was all she seemed capable of saying, as she got her breathing more under control, but the look in her eyes was a sort of excited and satisfied look, that I thought meant she knew what it was about now, or that at least she had experienced something she had needed to do.

I held tightly onto the condom as I slowly withdrew my cock before it softened. I didn't want any of my copious cum to get inside her.

She felt what I was doing, "Can I see, you know, what's in it?" she asked, more boldly than she had sounded before.

"Errr, yes," I said, holding it out to her.

She took it off me and squeezed the end where all teh cum was, making it move about inside the thin sheath.

"Gosh, there is a lot, I didn't think there would be that much Is it always like that?" she asked, still fascinated by what she was seeing.

"No, not always," I replied, "but often quite a lot."

"And it only takes one of those microscopic things," she mused to herself, still prodding the teat end of the condom.

"Yes, it does," I confirmed, reaching out and taking it safely from her. I didn't want any accidents.

"I wonder what its like to feel you actually squirt that inside me," she said next, her eyes still on me holding it.

"That's something we can't do," I said firmly.

She lay there sexily naked, apart from her skirt which was still rucked up around her waist, and looked at me with those big blue eyes, "We could if I were on birth control, couldn't we?

I felt I could almost look through them and the see the cogs going round in her head. My cock began to stir at the thought of how it would feel to release my sperm directly inside her, and I had to quell the desire before we did something stupid.

I stood up and reached for my clothes, "We might," I said, "but for now, I think I need to make sure you get home safely before someone comes looking for you."

"You're right, it is very late, but don't worry, if anyone asks, I'll just say you were later coming home than you thought," she said, picking up her panties and sliding them up her slim thighs, "I'm beginning to think I might be a bit sore tomorrow," she grinned, "but it was worth it."

As with Cass, I thought she might be doing much more babysitting for us in the future.