Babysitter Deb, the First Encounter

My wife Erin and I don't get to go out often but when we do we always try to make the most of it, whether that be to find some erotic play or just to go out dancing or dining. We're into the swinging lifestyle and enjoy the odd get-together. The very odd time we'll go out overnight and when we do we try to have a babysitter as our youngest is old enough to be home alone but we prefer him to have someone older here just in case something were to go wrong. Wasted money for the most part but peace of mind also.

We don't have a regular sitter because we so rarely require one but we have a few we use. We wanted to go out overnight last weekend but made the decision fairly late in the game. As a result, we were scrambling hard to find someone as most already had commitments. Working our way down the list we ran out of our regulars. One of the regular girls suggested that one of her sisters might be able to help us out. Once we had no other options, we rang her sister Deb and she wasn't doing anything that night and agreed to come look after our son for the evening.

Deb arrived at the expected time. We were fairly surprised by her appearance. We hadn't seen her in years and she'd grown into quite the stunning young lady of 18 with pale blue eyes, black hair, a decent sized chest and tight waist and butt wearing a tank top and skin tight jeans. I felt a bit of a tingle in my groin when I got a good look at her and planned to take it out on Erin later that night.

Erin and I headed out for dinner and dancing, looking for trouble but we were having no luck. Every single person we came across was not someone either of us were attracted to, and no couples seemed to be into the lifestyle scene. This is what we got for leaving things to the last minute and not making plans ahead of time. We eventually made our way to our hotel room but were also disappointed to find that it was on a very busy road and extremely loud. This was an issue for us because we live in an extremely quiet area outside of town and are used to quiet.

As a result of our lack of success in finding someone to play with we laid down together and started a bit of petting and dirty talk. I was surprised when Erin brought Deb's name up. She asked me if I'd noticed how cute she was. I obviously answered that I had noticed. Erin had seen me sneak a few glances at Deb and it got Erin's thoughts wandering. Erin mentioned Deb's age and that she was legal. "Yeah?" I responded, "And what are you thinking?" I asked. Erin replied that it would be amazing to share Deb between us one day and I agreed. She also said she'd love to watch me with Deb which I again agreed would be hot. We continued to have sex with lots of talk of Deb and once we were done we showered up to finally lay down to sleep. Unfortunately, the noise of the road next to the hotel left Erin and I awake, we were not getting any sleep there that night. Finally around midnight we decided to throw in the towel and go home. We figured we'd just leave Deb in the guest room where she'd be asleep and one of us would drive her home in the morning.

We got home shortly after 1am and as we walked towards the house we noticed flickering light in our bedroom which surprised us a bit. I usually lock out my computer when we're out as I have a lot of dirty porn of us and "guests" on my PC, and we don't have a TV in our room. I pointed out the light to Erin and she agreed with me that we should quietly go to the window to see what was happening.

As we got to the window and looked in I was surprised but excited to see Deb sitting at my desk. I'd obviously forgotten to lock out my computer before we left that night. On the screen was a home video of ours. It was a video which was one of my favourites where we had another couple over, resulting in all of us fucking for most of the night. The movie was at a scene where Erin was filming me fucking the other wife with lots of close-ups of my cock going in and out of her. Most of our playing involves other men and me sharing Erin.

Deb had her shirt pulled up and her jeans off, her legs were bent up with her feet resting against the edge of my desk and she was playing with her pussy. Erin whispered in my ear "she seems to like watching you fuck". I nodded in agreement and we both kept watching. I felt my pants getting very tight as my cock grew hard again. Erin reached over to my crotch and started to rub my cock through my jeans and whispered "you seem to like watching her too?" Again, I nodded in agreement. "Me too" Erin said. I looked over at Erin to see her hand down her pants and she was now rubbing herself also. Then Erin said something which surprised me, "I think you should drive her home and let her feel the real thing".

We pretty much always play together so I wasn't quite sure how to react to Erin's suggestion. Of course the idea excited me and I replied "You think so? I'm twice her age, she won't have any interest in me." Erin replied "she seems to think you're pretty hot" and motioned towards Deb. I focused on Deb again. Her hand was moving at a very fast pace, her young firm breasts were heaving as she breathed hard. It was obvious that she was very close to having an orgasm. Erin whispered "let's wait until she cums, then we'll kill 10 minutes and go inside so she has time to dress. I want you to take your phone before you leave to drive her home, call the house and let me listen to what happens while you're with her." I nodded again having nothing to say.

I couldn't believe that Erin was going to let me try to seduce this young vixen babysitter. We watched Deb a while longer and she finally stopped touching herself, shut down the movie and got dressed. We realized that she hadn't cum but Erin pointed out that many women never do, especially at Deb's age, a fact that I'd forgotten as I hadn't been with anyone Deb's age in decades.

We finally made our way to the front door. Deb was now on the sofa watching a show and was very surprised to see us. We explained that we couldn't sleep at the hotel and decided to come home. I asked Deb if she wanted me to drive her home now but we'd still pay her for the entire night regardless. Deb felt it would be best to get a good sleep in her own room so I would drive her home. We paid her for the babysitting and prepared to head out.

I kissed Erin good-bye and she smiled at me and motioned for me to ring her, something I nearly forgot to do. Deb walked out ahead of me and I could barely take my eyes off her firm ass long enough to dial the house and slip my phone into my pocket so that Erin could hear everything. We got out to the truck and started the drive home.

I really had no idea how to approach making a pass at Deb. We likely had very little in common. Finally I spoke "you've turned into quite the beautiful young lady Deb." As soon as the words left my mouth I felt like an old pervert and regretted speaking.

"Thank you. You're just as handsome as I remember" Deb replied. Apparently she didn't mind my comment, opening the door for me to say more. I asked if she had a boyfriend to which she replied that she didn't. "The boys my age are all so immature. I can't be bothered with them". This was definitely going in the right direction.

Finally, I asked "do you want to go straight home or would you prefer to go for a bit of a drive?" Deb looked at me a bit perplexed. I smiled at her and gave her a wink and I could see the look of comprehension as she figured out what I was hinting at.

Deb's cheeks went red and she smiled at me and replied "a drive would be nice".

My pants were now straining hard. All I could picture was that young body that I was staring at through our bedroom window and it was driving me crazy with lust. I took a turnoff at an old dirt road which led to a bit of a lookout and once we arrived I shut the truck off. We made a bit more small talk and I finally got the nerve to lean over and kiss her. I was met with a very eager mouth and tongue. I didn't know how much Deb wanted to do so I took things slowly. I nibbled on her ear, then her neck. Her breathing was getting very heavy and fast and I took that as my cue to move forward. I slid my hand to her waist, then up to one of her breasts. Deb let out a very quiet moan as I found her nipple through her shirt and bra. I now slid my hand slowly down her front to her thigh, then to her knee, then to the inside of her thigh. I felt her spread her legs slightly and I continued until I found her crotch. It was extremely hot and obviously damp. I started to rub her through her jeans and she moaned more as she started to grind against my hand. "Is this okay?" I asked.

Deb nodded, her breathing was getting more raspy and harder still.

"Do you want just this or do you want more than this?" I whispered into her ear.

Deb looked me in the eyes and panted out "more please".

I then told her to "let me know if you want me to stop at any point". The last thing I wanted was to take advantage of a young girl like her.

I lifted Deb's shirt up over her head, then reached behind her back to undo the clasp of her bra, removing it. Her breasts were truly spectacular. They were round with no signs of gravity working on them, soft, and easily a full C cup with small very perky nipples. I lowered my head and nibbled on her nipples, and while I did I reached past her and pulled the handle on the side of her seat to recline it. Now I started to work at her jeans. I unbuttoned them, then slowly slid her zipper down. Her jeans were so tight that I couldn't even slip my hand down the front of them so I asked her to "take your jeans off please".

Deb kicked her shoes off, then lifted her bum off the seat and wiggled her jeans down and off leaving her panties on. Now I proceeded to slide my hand back up the inside of her thigh to her panties, they were extremely damp, showing her excitement. I began to rub her crotch and again she ground against my hand. I wanted that pussy badly! I slipped her panties to the side so that I had access to her flesh. Her pussy was completely shaved with very small lips. I parted her lips and slid a finger into her easily due to her being so wet. As I started to finger her she really got going, her breathing was hard, she was panting and moaning, her back was arching and she was grinding on my hand.

I asked her "are you going to cum on my hand?"

She shook her head and whispered "I can't cum, I never have."

I smiled at her and said "we'll have to see if we can change that."

I continued to play with her pussy, working gently at her clit and sucking on one of her nipples. Deb was obviously very close to an orgasm but not quite there. After a while I leaned back in my seat and unzipped my pants, pulling my straining cock out. At the same time I discretely slid my phone from my pocket and placed it face down on the dash so that Erin could continue to hear us.

Deb wasted no time in getting to her knees in her seat and leaning over to start sucking on me. She didn't mess around at all, no licking or teasing, just straight to sucking. Her technique left a lot to be desired but her enthusiasm made up for most of it.

While she was sucking on me I slid my hand under her and between her legs so that I could continue to play with that beautiful pussy of hers. While she bobbed on my cock I again pushed her panties to the side and fingered her, keeping her extremely excited. Finally I asked her "are you ready for me?"

Deb lifted her head and kissed me hard. She pulled down her panties and started to try to climb over onto my lap which wasn't going to happen in the driver's seat. I told her to sit back and stay there for a second. I kicked my pants off completely, pulling a condom from my jeans, and put my shoes back on, exiting the truck and went around to her side. I opened her door and took a moment to admire her young tight body. This girl had a body that would put most porn stars to shame. So tight and toned, curvy and soft all at the same time and in all the right places.

Deb turned to face me now and swung her legs out the side towards me. I got to my knees in front of her. I had to have a good look at this young pussy and I wanted to taste her also. Her pussy was as beautiful up close as it had appeared from inside the truck. Her lips were tiny, her slit was small, I had to taste it. I leaned in and licked the length of her slit, sending a shiver through her body. I then slid a finger into her and started to move it in and out as I licked and sucked her clit. I got her very worked up and lubricated for the next move.

I now stood between her legs and above her glistening slit, then I stepped forward as I ripped open the condom package and started to put the condom on. I rolled it down over my cock as I looked her in the eyes, watching her as she stared at my cock and watched what I was doing. I leaned forward now and placed my cock head at her entrance. Her pussy looked so small and tight with my hard cock against it.

I asked again "are you ready for me?" She nodded and wrapped her legs around me, grabbed my cock with one of her hands and guided it into her as she pulled me forward. I couldn't remember the last time I'd been in a pussy this tight. At first I didn't think we'd be able to have sex. My cock wouldn't go much past an inch or two into her, but then slowly her insides relaxed and I was able to go deeper.

The sensation was incredible and as I worked my way deep inside her she let out a very loud moan of pleasure. "Please fuck me! Fuck me!" she pleaded. I started out slowly, truly enjoying the feeling of stretching that young pussy, then worked up my pace until my balls were slapping against her ass hard with each thrust. She was squirming and moaning, pulling me into her.

I finally had to stop for fear of cumming too soon. I pulled out, took her hand and pulled her from the truck. I turned her around so that she was bent over the seat now. I had a good long stare at that tight ass of hers before stepping forward and pushing my cock into her again. She nearly screamed this time, crying out "oh yes! Oh God you feel so good! I needed a man's cock!" It was obvious that the boys her age weren't cutting it and I wanted to ensure she always remembered the difference.

I now continued to fuck her hard and deep, holding her hips and pulling her to me with each thrust. Again, after a while I had to stop so that I didn't cum. I reached into the back of the truck and pulled out an old blanket we keep in there and laid it on the ground next to the truck.

I pulled Deb to the ground with me. "Now we're going to make sure you cum" I said to her. She smiled and said that she didn't think she could. I asked why and she shrugged her shoulders. I smiled at her and said not to worry, that we'll make sure she did. I laid back and pulled her on top of me. She straddled my lap and finally pushed down when she found the head of my cock at her entrance. The sight of her on top of me was something I'll never forget. She sat upright on me, bouncing on my cock and squeezing her tits together as she played with her nipples. I took one of her hands and slid it from her breast, down her tummy to her pussy.

"Play with your clit for me" I commanded. She did as instructed and was having a lot of fun but I could tell she wasn't getting there still. Finally I asked her "Do you trust me?" Again she nodded. "I'm fixed, clean and tested regularly so you don't have to worry." I lifted her off my cock and pulled the condom from it, then rubbed it up and down her opening and finally thrust back into her and pushed her down on me.

"Oh my God!" she cried out. "I knew it would feel better without one but I had no idea!" Obviously she'd never had sex without a condom. Again I made sure she was playing with her clit and I worked my hands all over her young body. "Don't be afraid" I assured her, "You have nothing to be embarrassed about. The hottest thing there is for me is watching a woman cum."

My encouragement seemed to give her some confidence. She started to fuck me faster and her hand was working her clit feverishly again. "That's it baby, you look so fucking hot bouncing on my cock." Every time I spoke she seemed to get lost deeper in pleasure. "I want you to focus on how good it feels to have me inside you" I continued. "Fuck me, fuck me faster, fuck me hard" I encouraged.

Now Deb started fucking me like an animal. "Your bare cock feels so good inside me" she panted out, "I think I'm going to cum. Yes, yes, yes, I'm cumming, I'm cumming!" she screamed. Her entire body went rigid, her back arched and her head tossed back at the sky. Her pussy was contracting on my cock and it felt like she was trying to milk me. It was like she had years of orgasms pent up inside her and they were all coming out now. Her body just kept shaking and twitching on top of my cock and it was becoming extremely hard for me to not cum also.

Finally she regained her composure and laid down on top of me panting like a dog. She kissed me deeply, thrusting her tongue into my mouth again, my rock hard cock still inside her. I ran my hands up and down her sides, finally resting them on her ass which I fondled and squeezed.

"My God! I had no idea. Thank you." Deb whispered to me finally after pulling away from my mouth. I told her not to thank me and I chuckled a bit. "Now I want to make you feel that good" she smiled at me.

She lifted herself from my cock and slid her body down mine until her mouth hovered over my cock. It was shining in the moonlight, completely drenched in her juices. She grabbed my cock and pulled it up and into her mouth and started to suck me again. Once again, she was enthusiastic but not great at it, something I hoped to have an opportunity to coach her with in the near future. After a minute or so I pulled her mouth off me. She looked up at me with a hurt puppy dog look "doesn't it feel good?" she asked.

I had to be careful with my reply, I didn't want to hurt her feelings and take away from what just happened. "Yes, it does feel good, but that's not what I want" I answered. "Maybe some other time you and I can work on showing you what really makes my cock go crazy with your mouth, but for now I need to be inside you again." She smiled at me so I knew I'd handled this well enough. "I want to look you in the eyes while I cum" I said, "now lay on your back for me".

She did and I crawled up between her legs. I stayed on my knees, holding my cock with my hand and ran my head up and down her opening, taking time to squeeze some precum from it and show her. "See how hard you make me? There's already cum leaking from me." I pointed out.

Deb grinned, "please fuck me again" she pleaded. I guided my cock back inside her opening. Just as before, the feeling was incredible but now I wasn't trying to hold back. I grabbed both her legs and worked them up onto my shoulders, then I leaned forward so that I was on my hands, holding my body up over her so that I could watch her. I started fucking her, slowly at first but speeding up quickly. I watched as her young tits bounced up and down with each thrust.

I looked down to watch my cock sliding in and out of her tight pussy. "Do you want my cum?" I panted out.

"Yes, please cum in me" she pleaded, "I've never had cum in me". Well needless to say, that was all it took for me.

Within a few more strokes I grunted out "Fuck Deb, I'm going to cum! Fuck I'm going to fill that young pussy of yours! You ready?" I'd no sooner finished asking when she wrapped her arms around me completely pulling me into her, clawing at my back while yelling "Yes! Fill me!" And fill her pussy I did. Everyone who's ever seen me cum is amazed by the sheer volume of what I produce. I literally explode so much cum that it sometimes frightens people.

There I was laying on top of this young beauty, her legs on my shoulders, her arms now wrapped around my waist also pulling me into her, my balls spasming over and over as I pumped my seed into her, I was in heaven.