Where it happened: Babysitting house
Langauge: English
Sex: Male
Rating: 10
Category: Straight
Babysitting with Ann
Ann and I had been going out together for about five months. She was my first girlfriend just as I was her first boyfriend. She had taught me to kiss, practising with our mouths open and breathing through the nose. Once we had one long kiss all the way through the longest tunnel in England. We touched each other only up to certain limits. Mostly I stroked her back, firmly, softly, lightly; just kissing and stroking until my groin ached. I could run my hands up her side so that my thumb strayed onto the swelling of her breast but she would not let me touch her more. I thought that this was because she would not enjoy it, whereas she was trying only to keep our increasing passions under control.
A couple of days before she said she could not go out with me that night because she was going babysitting. The area was known as Stork Island. It wasn’t really an island at all, just a modern development of compact houses. She said I could come to keep her company. She had cleared this invitation with the couple she was babysitting for because they had laid out some supper for both of us. They gave us knowing looks as they departed. At the time I just felt the charged atmosphere, now I think they were just remembering what young love had been like for them only a few years earlier.
We were tense, or I was particularly tense. We did not have other opportunities to be alone together in a warm, comfortable house, where it was guaranteed that we would not be interrupted. The two children were both under the age of three and were sound asleep when we arrived. It was highly unlikely that they would wake, and if they did they would cry for someone to come to them.
We ate almost without speaking. I felt something special was going to happen but did not dare to think it through. We put on some music, and Ann took me by the hand. First we kissed as we were accustomed to do. I stroked her back and she held herself close against me. But when I started to stroke a bit more round the front she did not clamp my hand with her arm as usual. We lay down on the carpet in front of the gas fire on our sides, kissing, kissing. The she rolled onto her back a bit so that my hand naturally came over her breast. Round and round I stroked as she smiled and became flushed in the cheeks. Then she shocked me by asking whether I wanted her to take her blouse off. I don’t think I really replied, it was something I had wanted but had not dared to think could happen. She sat up briefly and efficiently removed her blouse and bra. As she lay down again I almost did not know what to do. My prick had been erect for what seemed like hours already and was aching as it was as hard as it would go. I stoked Ann tentatively. Just gently round her breasts and across her nipples. I really had no idea what effect this was having on Ann. Gently, gently backwards and forwards, round and round over the nipple, holding the nipple ever so gently between thumb and forefinger. By now Ann was breathing heavily, her neck and chest were reddened, and her eyes were half closed. Now she said she wanted to stroke me too. She sat up again and helped me remove my shirt, and made as if to undo my belt. I removed my trousers and she then half pulled down my underpants, so I did the rest. So there we were with me complete naked and seeing Ann’s breasts for the first time. She obviously had planned this as she did not hesitate to unbutton her waistband, unzip her skirt and pull both it and her panties down.
I had never seen a naked girl before, nor had Ann seen a rampant young male before. She lay back again while I looked at her. Her arms were by her sides, her legs together, her pubic hair was all squashed and her little nipples standing up. I was scared, this was a whole new area of experience to me. I did not know what to do. I knew of condoms. They were always at the hairdresser’s, who were wont to say “Would you like something for the weekend, sir?” with a knowing look. But I had certainly never bought one, and I most definitely knew exactly where babies came from and being just sixteen and a hard working student certainly did not want to start breeding then. I was almost trembling, maybe I was trembling for Ann knew I was troubled.
She started to kiss me again. We were used to kissing and it comforted me, my erection regained its previous rigidity. When we broke off from the kiss I looked at her again, the rounded breasts, the join between her thighs and her pubic hairs. I made to start kissing her again. “Don’t you want to touch me?” she asked. I started again to stroke her breasts, again round and round, from one side to the other, then more strongly moving the flesh of the breast from side to side. The excitement was immense and the tension grew again between us. Then she lightly held my wrist and guided my hand lower, onto her stomach and down. I did not know what a vagina would feel like. I explored it gently. It was very moist and slippery. The hairs were hard against the soft slippery inner lips. She said what was nice for her. “Nice” was a word I had been taught never to use, the English teachers said it was a weak, indefinite adjective and that I should always use a more precise word. But when Ann said “That’s nice” I don’t think there could have been a better way of expressing it. Ann opened her legs a little more so there was an easy gap between her thighs. My fingers went from the very back to the very front dipping in gently and up and over her clitoris. I was not so familiar with anatomy at that time, I had no words for the different bits I was encountering, I was just feeling, stroking, exploring, caressing.
I began to learn how she liked to be stroked down there when she moved her hand towards my penis. She rolled over a little and held it between her hands. Having my penis held was a whole new experience for me. I had masturbated, of course, but that was me holding it not anyone else. My penis was something I had kept to myself. So when she held me I found that I had been so close to coming for so long that I came almost instantly. It came in a big rush all over her hands, wrists and arms. It spurted so hard that some of it splashed onto her breast. Ever in control, she said that that was alright and she was glad that I had come. Then she went to the kitchen and cleaned us both up with tissues and got a cloth and cleaned the few spots from the carpet. I felt stunned. There was this naked girl, not being modest and hiding herself under bras and petticoats but walking about the room with not a stitch on, just as I was still lying as she had left me, my slightly wilting penis across my stomach.
She came back and looked at the clock. It was still only just after 9 o’clock The couple were at the cinema and would not be back until about quarter to 11.
“Now its my turn” she said. I was not sure what she meant but she snuggled up against me and took my softish cock in her hand. “Now I want to look at you”, she said as she propped herself up on her elbow and looked down me. “Tell me what’s nice”, she said as she started to move her hand. She tried running just the very tips of her fingers up and down the shaft, she tried holding the shaft firmly, she lightly scratched her nails over the bag of balls. She tried to grip the balls firmly, but didn’t do it again. The penis started to weep and she smeared the colourless liquid around the head of the penis. I said she should rub it up and down. “Like this?” she said as she started to do it. But than she became playful and would not really do what I wanted. A light touch here and a squeeze there. She was arousing me more than if she had just done what I wanted her to do most. Suddenly she put her leg across me and knelt up. Her vagina centered on the middle of my shaft. There must have been millions of only recently ejaculated sperm drying out all over my stomach. “Its alright”, she said “I’m using a sponge, I can’t get pregnant, but just to be doubly sure I’ve brought you a condom.” Her bag was on the floor near the fire and she leant over for it, her breast came near to my mouth so I gave it a little kiss. She sat up again and fished around in her bag. A packet of three was revealed. She took it out and put it on the floor beside us.
It had all become a little clinical as if there was a proper procedure rather than just loving and feeling. Ann could see that I was not quite ready for her. She had been planning all this for weeks, I learnt afterwards. She had established her credentials as a babysitter and had sat for various couples before choosing this one to invite me to. I had thought she had just been doing her homework. Well she had in a way because babysitting is a good opportunity to get on with homework in a quiet house. But she had carefully chosen this house and had planned carefully.
“Do you want to see what I like to do?” she asked. She was still kneeling over me, and moved her cunt backwards and forwards a little. One hand crossed over her chest and moved tentatively up towards her breast. She ran the tips of her fingers backwards and forwards.
“Watch me carefully then you will know some of the things I like.” Her nipple started to pucker again and I could see it had become hard. She licked her fingers and returned them to the nipple. Backwards and forwards she stroked gently, then she suddenly squashed the whole breast with her entire hand, kneading it with the fingers sunk into it. I could feel her wet cunt on my cock. These words that I had known for years were starting to become useful and meaningful, rather than just dirty words to be sniggered about. She slid herself up and down, looking at the head of my cock as it became visible. Her other hand went up to caress the other breast and she started to move more rhythmically. She looked me straight in the eyes, her eyes were becoming wild absorbed in what she was feeling. Her right hand, she was right handed, came off her left breast, flirted briefly across her belly and sunk into her cunt. Wet up to the second knuckle her middle finger rubbed her clitoris. Faster and faster. “Look at me” she cried as her other hand pulled up the skin above her cunt to expose herself fully. I lifted up my head to see her finger flashing up and down her clitoris. She rocked and gripped me with her thighs and cried out uncontrollably as I watched her bring herself to the first orgasm I had ever seen.
“Do you want to fuck me?” she asked. “My cunt is still aching. When I come like that, just rubbing my clitoris, its good but there is still an ache inside me. Sometimes, in bed, I can come four or five times like that, but there is still an ache. I think what I need is your cock inside me. I love you and I want you to fuck me.”
“Haven’t you tried anything else?” I asked. Although this was all a new experience for me my mind was still working. I knew nothing about dildos and vibrators at this stage, but I just thought that if she needed something inside then she ought to put something inside.
“Well I do have a hairbrush.”
“Isn’t that a bit scratchy?” I had just had my first feel of the soft silkiness of the entrance to her cunt and could not imagine a bristly hairbrush in there.
“Not the brush end, you fool. The handle is smooth and rounded, a bit smaller than your cock and not as long. But if I lie on my back with my knees up I can use one hand to move the hairbrush handle inside me while I tickle myself with the other.”
Ann came and lay down beside me again and the release of pressure on my cock allowed it to start swelling again. Ann stroked it slowly and smoothly. It was all slippery with the juices that had run out of her and she just ran her hand up and down, closing it over the top and pulling the skin down slightly as her hand went down again.
“I love the smell of you.” she said. “It’s a special smell that’s not how you are usually.” Like most teenagers I did not want to smell at all, and spent considerable time in the bathroom showering and putting on aftershave and underarm deodorants. “Its nice” and she leant forward and kissed my tummy button. Ann’s hair was short, I think its called an urchin cut, it comes down to about the bottom of the jaw, but still it flopped over her face a bit. She held it back with one hand as she licked my stomach. My cock was so close to her head I was not sure what would happen next. I moved my hips so that my cock touched her on the cheek. She leant her head back against it, rubbing her cheek and ear on what remained of the slipperiness. She licked my tummy again and I knew I wanted her to lick my cock. She rearranged her legs so that she was kneeling beside me, holding my cock, then she bent forward. “It tastes of both of us. I know my taste because sometimes after I have been playing with myself I put my fingers into my mouth. I started it because I thought if a man was ever going to lick my cunt I ought to know whether it tastes nice. Your taste is quite different and much more salty.” I was not too keen on this analytical description but her mouth was now running up and down my again rigid penis. One hand was round my balls, holding them ever so gently, and the other was guiding my cock up to her mouth. She closed her mouth round the whole head of my cock. It was such a different and encompassing feeling that my hips jerked upwards and my hands gripped her shoulders. She pulled back a trifle and I calmed down. I slid one hand under her so that I could stroke her breast and she let out a gasp and wriggled her nipple against my fingers, and I knew I should have done it earlier. There was so much to learn about how to make love. She sucked and licked, stroked and gripped, caressed and tickled. I wondered how long this could go on for.
“I think you’re ready now.” She said, and picked up the packet of condoms. Quickly tearing the packet open she took one between her fingers and placed it on the end of my cock. “We were shown how to do this in our sex education classes” she said, “but not with a real cock to practise on.” She started to roll it down but it wasn’t as easy as it had seemed in the classroom. But she pulled at it a bit more so that it was well down. Then she leant over to her bag again and pulled out a towel. “We don’t want to leave any evidence.” She spread the towel on the carpet in front of the fire and placed her hips centrally over it. Opening her thighs she pulled me towards her. It is one thing to think about fucking but something else to actually do it for the first time. Here we were, naked for the first time together, and Ann was spreadeagled in front of the fire urging me to end her virginity. My cock was so swollen with all the attention it had been getting, and Ann’s cunt was as lubricated as it could be with all her anticipation of this important and unique moment in her life. But the actual mechanics of getting the cock into the right place was ridiculously difficult. My cock was very sensitive, full of feeling, but it did not seem to know which way was which. Ann moved her hips to try to help, from side to side a bit and up and down. Once I nearly went up the back passage but she quickly moved away. Then she put her hand down and firmly guided me into her. It went in a bit and then stopped. I knew about the first time and rupturing hymen, and that I should be gentle and that it would hurt the girl. Ann put her hands on my bottom and pulled me up, her legs opened even wider and I felt my cock penetrating deeper. I moved gingerly, pushing myself further up inside. Ann gasped and I stopped. I loved her too and did not want to hurt her. We were still for a minute and then Ann started to move again, gently rocking her hips forwards and backwards. She searched for my mouth with hers and sunk her tongue deep into my throat. Her arms were still down on my buttocks and she gently pressurised me into her. I don’t suppose my cock is very much different from anyone else’s, but it did seem to have a long way to go in. I pushed again and it seemed to slide in easily, it would slide no further. “Are you alright?” I asked “Does it hurt?”
“No its lovely. I must have done myself with the hairbrush or something. It feels fine.”
Then she started to move up and down, forwards and backwards in a sort of random pattern. I just lay there letting her do it and feeling what it was like to, at last, be doing it properly. My cock was stiff, but it had come once and seemed to be in no hurry to come again. Ann was beginning to enjoy herself, her movements were becoming stronger and her breaths were becoming shorter. I started to move in time with her as she moved up I moved down, and as she moved down I pushed into her or sometimes rocked from side to side pushing the side of my cock against the side of her insides. Her grip became fierce and one hand dug into the middle of my back. Suddenly her head was flying from side to side, it was as if she could not breathe and she let out a blood curdling scream. I felt her insides grip my cock in strong grasps, she was covered in sweat, and she shuddered to a halt.
It all happened slower that it takes to write it. I looked up at the clock and the couple were due back soon.
Ann said it was alright that I did not come inside her, she said I thought too much and felt a bit too little and that it didn’t matter because it was lovely for her and she loved me and I loved her so everything was alright and everything gets better with practice and lets have a bit of a wash and get dressed before they come back and she was babysitting again next week and would I like to come with her. And we both laughed and got clean and got dressed. And the couple came back and I was sure they could smell the special smell of lovemaking. And they gave us knowing glances as I stammered and stuttered and Ann was all efficient and workmanlike and arranging the time for next week.
The second time was not the same.
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