BabySitter's First Time(s)

It happened just after I turned eighteen. I was still at college and had a part time job so that didn't really leave me much time for myself, but I managed. What personal time I did have I tended to spend with my boyfriend, Bryn. We'd go on the occasional date and just have a bit of fun.

After I turned eighteen that fun started to take on more adult connotations. The amount of kissing increased and I was permitting petting that I'd never permitted before. We hadn't gone all the way at this point but I guessed it wouldn't be all that long before we did. Maybe. Maybe not.

Neither Bryn nor I had a car at this point. Licenses, yes. Cars, no. This didn't really matter as we both lived close to bus routes and a train station and the public transport was reasonable. If necessary I had a bike.

One Friday night I had a date with Bryn. He had a little extra cash and was taking me to a dinner and the cinema in town. (His idea. I pointed out that he'd never save enough for a car if he kept blowing his bonuses, but he didn't care.)

We took the train to the city, had a very nice meal, and watched a reasonable movie. It wasn't what either of us specifically wanted to watch but was a reasonable compromise, neither of us wanting to see the other's choice. (What is it with boys and violent movies?)

Coming back on the train we managed to score a carriage that was fairly empty so we snuggled away in a corner, all alone and unobserved. With half an hour or so to go on the trip a half an hour or so of smooching and petting took place. (Naturally)

Finally at our station we headed homeward. (My home, anyway.) Bryn decided that a little detour was required.

"Where are we going?" I asked and he grinned.

"If we go down here we can take the laneway through to the park, stroll through the park, and come out on the other side just a short walk from your place. True it's a little further, but only a little, and we come to your place from the other direction."

He was right so I didn't object. The weather was fine, the night still warm, and a full moon shedding its light. We strolled through the park, hand in hand, just taking it easy and enjoying each other's company.

Reaching some back fences we paused.

"We seem to have missed the exit," I observed.

"Nah, not really," Bryn said. "It's just a little further that-a-way. Before we continue on, however..."

He pulled me up against him and the kissing started again. After a while we sank down onto the grass, finding it soft and warm. Hands, his and mine, started wandering. Initially we were just stroking each other through our clothes but then Bryn started getting adventurous.

He flicked open the buttons to my blouse, his hands sliding inside, seeking and finding my breasts. Not to be outdone I undid the buttons on his shirt and started running my hands over his chest.

"You're somewhat hairy, aren't you," I told him with a giggle, my fingers plucking at some of his chest hair.

"You're not," came his reply, as he pushed my bra out of the way, his hands stroking my breasts.

All this was in accordance with things we'd done before, although not quite so blatantly. I simply enjoyed the touch of his hands teasing my breasts.

When one of his hands closed over my knee and started slowly stroking in an upwards direction I didn't notice. It took some will power not to notice, but I managed. His hand moved along the inside of my leg, finally settling on my panties, massaging me through them. This I noticed -- I just didn't complain.

Typical male he wasn't content with what he had. He wanted more. His hand went under my panties and his touching became a lot more intimate. Two could play at this game, I decided, and my hand started rubbing his shaft through his trousers. That's when I found out why his hand went under my panties. He wanted the closer contact and now that I was rubbing him, so did I. I unzipped him and found that closer contact.

He made a kind of hissing noise when I started stroking him but I ignored that. I mean, my panties seemed to have drifted down, giving him free range, and you didn't see me complaining.

This was a little further than we'd ever gone before but I didn't mind. I could always call things to a halt whenever I wanted to. We kept on playing with each other, me getting more and more restless as things progressed. Bryn now had a couple of fingers inside me, stroking me, and I was all hot and bothered. I swear, if he kept on going on at this rate I was going to have a climax. I wondered if the same applied to him, the way I was stroking his erection. It was big and fat and hot and he was starting to squirm a bit under my touch.

The squirming applied to me, as well. I was twisting about, wondering if he intended to keep fingering me until I had a climax. I wasn't going to complain if he did. There again, that would mean I'd have to stroke him until he came, and then I'd have to aim him so he didn't splatter me. Something to keep in mind.

His toe slid over my ankle, drawing it further to the side. Turning my attention from Bryn to myself for a moment I got a slight surprise. My blouse gaped open and my bra was pushed up away from my breasts. My skirt had managed to bunch itself up around my waist while my panties were down past my knees. While I still had all my clothes on I was effectively naked and way too aroused.

Bryn suddenly pulled away from me, his cock coming out of my grasp. Then he was pushing his trousers down, his cock standing way out, and he was kneeling between my legs. He leaned over me, his cock already pressing against my slit. He was looking at me and I was simply looking back at him, saying nothing.

He started pressing against me and just like that his cock was pushing into me. I found that I was holding my breath, watching his cock disappear into my body, feeling it moving into me. I felt a bit of a twinge when my cherry got popped but that was a nothing thing compared to what I was feeling as his cock descended.

His groin slapped against mine. Bryn paused for just a moment, and then pulled backed. He sure didn't stay pulled back, driving back in hard and fast and it felt marvellous. He started thrusting in hard and fast, seeming to be in a dreadful hurry, while I saw no reason to hurry.

Whatever, I was so close to a climax when he started that it took hardly any time at all and I was climaxing, strangling a scream as I went up in flames. (No way was I going to scream while getting laid in a public park.) My climaxing seemed to be the cue for Bryn to fire off, gasping and jerking as he cut loose.

Fortunately I had a small pack of tissues in my bag which I now put to use, cleaning myself up. Once we finished tidying our clothes we walked on to my place.

Actually, I walked. Bryn was strutting along like a rooster that had fucked an ostrich. One look at him and everyone would know he'd scored. That wasn't going to happen.

"I wonder what my dad will say if he guesses what we did," I said.

Bryn deflated like a burst balloon.

"What. You're not going to tell him, surely?"

"Of course not. But he is a very astute observer. He might guess by looking at us. Ah, no, I'm sure he wouldn't."

Bryn was now lagging slightly as he escorted me. I suspected that he wouldn't be coming inside with me when we got home which I didn't mind.

I was right. Bryn kissed me goodbye at the door, telling me he'd call me the next day. I went in and went to bed. I contemplated what had happened once I was in bed.

My virginity was lost, and that had been effectively painless. I'd been decently fucked. On second thoughts, I'd been fucked but it was only an average performance. While enjoyable the whole thing had been over far too fast. I'd started climaxing almost as soon as Bryn had started action, and his action finished just as fast. If he hadn't had such talented fingers I suspect that I might not have climaxed at all. Something to think about. Would I let him do it again? I wasn't sure. Another thing to think about.

Not unexpectedly Bryn called me the next day. We talked for a while but I put him off for our next date. Quite legitimately, too. I had engagements for the full weekend what with work and other things, and for the standard week days I had college, including a lot of homework. We arranged a tentative agreement to go out on the Friday, as long as nothing else cropped up.

This particular Saturday I also had a baby-sitting job, one of the last customers that I still sit for. I'd been easing all my old customers off to the younger sisters of a couple of my girlfriends. I'd probably recommend one of them to the Burkes when I saw them that night. Sitting cut too much into my short free time.

It was a hot day and when the evening rolled around it was still hot. I dresses accordingly, a light blouse and my skirt, while long, was also quite light. I fronted up and greeted the Burkes and the children. I found myself looking at Andrew with a bit more attention than on other occasions. He was a big, solid, man. Not fat, just solid with beef. He was not a pretty-boy type, but neither was he a grotesque. Just a personable average man. (But a big one.)

I couldn't help comparing him to Bryn, who was coming off a little poorly. Probably unfair when you consider that he was forty to Bryn's eighteen. Unfortunately I also found myself wondering what it would be like if he fucked me. I'd bet it wouldn't be over in a flash like Bryn. (Or was I being unfair to Bryn? Was my memory plying tricks?) I determinedly pushed that type of thought from my mind. Andrew was a customer and married. Not a potential conquest.

I spent the next half hour while Meredith finished dressing playing with the kids and not ogling Andrew and wondering. I gave absolutely no consideration as to what he might be like as a lover. Several scenarios concerning seduction and/or rape did come to mind and were firmly ignored.

Meredith finally finished getting dressed, kissed the kids goodnight, and she and Andrew headed out the door. I'd have died of mortification if I'd heard the conversation that started as soon as they drive off.

"What's got you looking so smug?" Meredith asked.

"Young Felicity," Andrew replied. "Perhaps not so young now. I suspect that she's reached an age where she feels it okay to experiments a little. I further suspect that her initial experimentation went well and she's wondering what if. She was very carefully not running her eye over me while doing some of that wondering."

Meredith laughed.

"I think she turned eighteen about a month ago. She has a boyfriend, name of Bryn, I think. About the same age as her. If they did get together and it went okay then good-luck to her. Do you seriously think she was checking you out?"

"I do. I could practically hear her ticking off boxes. Older, tick. Experienced, tick. Married, tick. Big, tick. Gentle, tick. Adding the ticks she's got me in a box labelled seducible, but watch out for the wife."

"Are you going to do anything about it?"

Andrew shook his head. "I don't think so. Unless, of course, she jumps me, but I don't think she'll be that forward. I may tease her a little."

Meredith nodded and the subject was dropped.

I had an easy night of it. I don't know what the kids had been doing during the day but they were beat and went to bed like lambs, dropping off to sleep almost as soon as they hit the pillows. This gave me the rest of the night to lounge about and watch TV and contemplate life and what would happen when I next went out with Bryn. Wiser, I was thinking, not to yield a second time too easily. If I agreed to seconds he'd have to work for it.

Andrew and Meredith eventually arrived home and wandered into the front room where I was watching the tellie. I politely rose to my feet, smiled, and asked them if they'd had a nice evening. Things got a little funny then.

Meredith said the evening was very enjoyable, but she had a funny smile, seeming amused by something, and she looked at Andrew and gave him a small nod. He looked just as amused but he replied to the nod with a slight shrug and an iffy motion with his hand.

That done he reached out and trailed a finger over my breasts. Over my cleavage, to be exact, tracing one breast down, following the bra line, until it met my blouse and trailing back up the other side, his finger on my actual breast all the way.

I blushed, staring at him.

"Do you mind?" I asked, trying for acerbically but probably just sounding breathless.

"No," he said, sounding happy about it, "and apparently neither do you."

With that he did it again, his finger sliding over one breast all the way until it met my blouse and then back up the other breast, but it was worse this time, as his figure slipped under my bra and he actually brushed against my nipples both going down and coming back up.

"You are offering them for a teasing touch," Meredith said, looking more amused than ever.

I was like, what the hell are you talking about, and looked down at my breasts. Talk about embarrassing. The top couple of buttons on my blouse had popped open showing a lot more cleavage than I would normally show. I had no idea how that had happened. I frantically grabbed at the sides of my blouse, trying to do them up.

"Allow me," said Andrew, brushing my hands away.

Blushing madly I stood there, feeling his knuckles brushing against my breasts as he worked at the buttons. I was way too late by the time I found out that he wasn't doing up the errant buttons. No, he was undoing the rest of them and my blouse now gaped open.

"Mr Burke," I snapped, feeling righteously indignant.

"That's me," he agreed, now running his hands over my breasts, sliding them under my bra.

"Stop that," I snapped. "You can't do that."

"No? Why not?"

"Because I don't like it and in case you've forgotten you're married and Meredith is standing right there."

"Oh, don't mind me," said Meredith. "A little on the side adds a touch of spice to our life. As for your not liking it..."

She stopped talking, reached over and pushed Andrew's hands away, which was a plus, and then popped the cups of my bra up and off my breasts, which was most certainly a minus.

"See," she said, tweaking my nipples. "They're standing out, wanting some more touches. Perhaps a kiss."

"Certainly not," I said while at the same time Andrew simply said, "Good idea."

Andrew had a hand on my back holding me steady while he leaned forward and his mouth closed over a nipple. He started lightly sucking on it and it felt, it felt, well I don't know how to describe it, but I could feel myself reacting. What was worse, instead of trying to push him away I was just standing there letting it happen.

I finally managed to tell him to stop it when he switched breasts. He took his own sweet time but he did stop. My nipples were wet and really standing out, my breasts feeling swollen.

"It seems to me Felicity that it'll be easier to straighten your clothes if you finish up taking your blouse and bra right off," Meredith advised. "Try it now and they'll get all tangled. Let me give you a hand."

My breasts were already hanging out so I couldn't really see where taking off my blouse would make things worse. Really, being able to put them back on properly would definitely be a plus. Meredith was helping me out of them before I really stopped to put any serious thought into it. Having her toss both bra and blouse to one side instead of handing them to me was a bit of a shocker.

"Very nice," said Andrew, while I quickly cupped my hands over my breasts, blushing. "You'll look even better with your skirt and panties gone."

"What?! I am not taking them off," I snapped at him, and he laughed.

"No need," said Meredith. "I can help you do it."

"What? No way."

"Why not? Haven't you ever been naked in front of a man before? It's exciting."

"No, I haven't and I don't want exciting."

Why did I have this feeling that I was fighting a losing battle?

"Of course you do," said Meredith. "It's even more exciting when you know he's going to make love to you, especially if it's the first time with that man."

"What do you mean, make love to me? Stop that."

While I was arguing Meredith had been acting. She'd flicked open the fastening on my skirt and was in the process of pulling it down, not forgetting to take my panties down at the same time. My protests were completely ignored and in short order I was standing there naked, not counting my shoes and socks.

I didn't know what to do. I was naked and Andrew was going to fuck me? They had to be kidding me. Even if they were kidding one big fact stood out. I was standing naked in front of Andrew. Me. Naked. Meredith was correct about one thing. It was unbearably exciting to be standing there naked knowing he might be going to fuck me. I could feel the heat and dampness between my legs.

I noticed that while Meredith was busy stripping me Andrew had taken his shoes off. I was wondering why his shoes when I found out. He dropped his trousers and without shoes in the way he was able to step right out of them. His undershorts, too, I noticed. That meant...

My eyes rose from his feet and I blushed. From the amount of heat in my face I must have had a cherry red face. Andrew had an erection and it was standing tall and proud and from the look of it, it had reason to be proud. That thing looked a whole lot bigger and fatter than Bryn's effort.

It wasn't only my face that was feeling hot. I was feeling quite a bit of heat generally, nowhere more so than in my groin.

Andrew started moving closer to me and I started nervously backing away. He's really going to do it a little voice was screaming to me and Meredith is just going to stand there and watch. How could she do that? For that matter how could he do that?

That last question was easy to answer. From the way his equipment was standing up he could do it very easily. Whether I could take it as easily was another question entirely.

I kept backing up until I felt a lounge chair behind me. Andrew moved a little closer and I was now leaning back against the arm of the lounge chair. This, I realised, put me in a position where he could do what he wanted. What the hell was I supposed to do now?

"You know, Felicity, if you're going to say no it might be a good idea to say it fairly soon. If you don't you might find it too late."

Andrew spoke softly and it took me a few moments to catch on to the meaning of his words. While I was puzzling them out he was stroking my slit with the head of his cock. I could see his cock rubbing against my lips, lips which I was shocked to see were wet and pouting.

If I was going to say no I had to speak up now? Did that mean he wasn't going to force me? Well, of course it did. If I was allowed to say no then he obviously wasn't going to just go ahead and rape me. I was still contemplating this piece of news when he seemed to twitch his cock slightly, my lips moved apart in a bit of a pout, and he pressed into the space provided.

The last part of what he said came to mind, namely speak up before it's too late. With that thing pressing against me it was way past time to speak up.

"Ah, I don't think, um, I mean, you shouldn't, ah," I mumbled, dithering when I should have been yelling stop. He treated my dithering in the way it deserved, by ignoring it.

By now I could see (and feel) that the head of his cock had pushed its way into me, starting to stretch me. He was so much fatter than Bryn. I was starting to wonder if this meant that it was now too late to object, finding out tout suite that the answer to that was yes as he was already pushing deeper.

He slowly sank into me, taking his time and not saying a word. All I could do was lean against the arm of that chair, feeling him go deeper and deeper. I was also not saying a word, but that didn't mean that I was silent. I was going ah, ah, ah, as he drove in, making startled little noises every time he pushed a bit deeper. (Meredith wasn't helping the situation at all as she was busy giggling as she watched it happen.)