Hot babysitter Cali Carter gets an anal fuck

Hot babysitter Cali Carter gets an anal fuck
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It was late Saturday night when I experienced a rush I never had before in my life.

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This was something I had always thought about before, but never followed through with, fearing for the consequences with my girlfriend. Until now, I had always considered this fantasy of mine to be just something in my mind that would arouse me from time to time, but nothing more.

I would fall asleep some times thinking and dreaming of it, but if ever this fantasy looked like it might became something more real, I just backed away from it altogether, scared of what might happen later on.

Before I tell you what that fantasy is though, I'd like you to now a little more about me. I'm 31 years old and I'm in a committed relationship with my girlfriend of three years. We are adventurous in the bedroom and all, but if there is one of us who is more risqué and daring, it is certainly me. For a long time my girlfriend and I would get into arguments about fantasies: I would like to talk about them when I'm aroused and intimate, but she never would.

She would always back off and say that she really wasn't into those things that I would talk about. This was something that I lived with and struggled with. I understand where she comes from on the subject, and to be honest, all of my talk was always just that… talk. I don't think, if ever given the opportunity, that I would do anything as wild as what I would describe to her.

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I just thought that it would be fun to play out some of those fantasies in our imaginations, just for excitement. Something changed the other night, however when just such an opportunity came up. For some reason, I still don't know why, my girlfriend let her guard down and we got to experience one of those fantasies of mine. It keeps running through my head over and over. Something changed that made this fantasy permissible. I think I know what it was (feelings for a younger guy), but regardless, I'm happy this feeling came over her.

My girlfriend is far from prudish, in fact she enjoys being a joker with people and often makes leud pranks that get quite a few laughs. She is often smiling and having fun with people and I frequently see her in large groups being social. She has an extremely athletic body and gets frequent attention from men, but she tends to stay away from aggressive guys and rarely flirts.

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It's kind of funny to watch guys come onto her, only to see them fail time and time again. Saturday night, however, she had made a remark to me about how attracted she was to one of the younger guys at the competition that we attended, which I was surprised by. It didn't bother me that she told me, in fact, I trust her because she tells me things like that.

This was unique, though. She rarely mentions her attraction to other men, though I frequently tell her how attracted I am to other women, or that I like a pair of breasts that I see (or many pairs!), or something like that. We're quite open about those types of things. But, I noticed her staring at this kid a few times that evening, and it was really cute to see her mild infatuation.

Every time he would pass by, she would make a funny face, or pretend she was mesmerized by his good looks. Everyone had a good laugh, but what was funniest is that I think she really did have an fairly large attraction to him. A few times, in fact, after hearing our group of friends laugh after he passed by, the kid would turn around and smile at my girlfriend. One time he even showed the group his abs, after one of our friends yelled out "Show us your abs!".

My girlfriend was pretty embarrassed by that one, because by this time, I think he knew what was going on. You can imagine then, how strange and coincidental it was to see, upon returning to the dorms that we were staying in, that this young man was one of our suite mates for the weekend. At first, I had to sit with the notion and think about it, as it was slightly unsettling to think of this guy being in the same suite as us for the weekend. Was my girlfriend going to sneak into his room at night or something?

If it were ANY other person in the world, I'd say no, but in this case… who knew? I had gotten past that little uncomfortable feeling pretty quickly, though, as I trust my girlfriend completely, and know that she isn't the type of person to do that stuff, even if she really was as hot for him as I think she was.

The rooms we were assigned to were set up to have a common area to the suite surrounded by four bedrooms. My girlfriend and I were staying in one of the rooms, and three other young guys were staying in the other three rooms. The suite was nice an accommodating, having a nice-sized television with a couch lining the living room wall, a small, but well taken care of kitchen, and two bathrooms.

When we arrived, we went directly into our room and placed our bags on the floor, undressing and getting ready for a shower. My girlfriend, her name is Tanya by the way, took the first shower, with me following after her. When I got out of the shower, I put on comfortable clothes and walked down the hallway towards the living room.

I had heard chatter coming from the living room, and saw that it was my girlfriend, the young man that she had a crush on, and another young man all talking together on the couch.

They had just finished showering as well, and my girlfriend was lifting her shirt up to show her abs to the young men.


What a flirt! She never does this, I thought. I made my way down to the living room area with everyone else and we watched TV for a good while. Tanya ended up sprawling out on the corner piece of the couch with the ottoman under her feet, with one guy on each side of her. I didn't think that either guy would make room for me, as they were obviously tired too, so I just sat on the lazy boy that opposed the couch.

From time to time the group would talk about something, and I could tell that Tanya was battling her tiredness in the interest of talking with the cute young guy she was hot for.

They would exchange a flirty glance once in a while, or give each other a hard time with something, but in a playful way. It was kinda cute. Tanya was drifting asleep here and there, and I could tell that she was still battling the fatigue and body aches from the competition. On top of the tiredness and aches and pains was an interesting situation in front of me. You see the fantasy that I have proposed to my girlfriend is that I would very much like to see her being intimate with several men at the same time.

I have told her how I would like to see her being touched by two or three men specifically- either softly and delicately with hand jobs and tit sucking, or maybe just kissing and fondling, or maybe just all-out slutty sex.

It's the idea of her body being admired, caressed, and enjoyed sexually by many men that always turns me on. I like thinking about what must be going through each man's mind when they're kissing her body, or sucking on her in some way- each person there is turned on by just a shared piece of my girlfriend's body.

This fantasy has never gotten me too far with Tanya, however. She gets turned off at the mere mention of a third person, and tells me that she's not that into it. Tonight, however, I figured there were two different angles that could play in my favor. For one, the young man that she had been flirting with all weekend was there and he would likely want to play with her as well, and two, she was sore and could be massaged by the young man… seemingly innocent at first, and then more heated later.

My strategy was in place! Tanya was starting to fall asleep, and like I had said, I could tell that her body was aching. I asked her about it. "Tanya, how are you feeling? Are you sore?" She was tired and responded that her legs hurt.

Perfect, I though to myself. "Well maybe this guy next to you would be nice enough to rub your feet for you. What do you think?". Tanya smiled slightly and made a yummy noise. I motioned to the young man and gave him the nod to proceed, which he did. I'm not sure Tanya could really tell what was going on, as she kinda laid there getting her feet rubbed while she fell asleep slightly.

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I then motioned to the other young man on the other side of Tanya to massage her other foot, which he did as well. You could tell that Tanya was liking the foot massages.

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She would come back to consciousness from time to time and made more yummy noises. She mumbled something like "that feels SO good…" or something like that. We couldn't tell.


I, sitting in the chair across from Tanya and the other two, was enjoying the show that I was seeing. Tanya was in the perfect position to be seduced by the two young men. You could tell, however, that they were treading lightly with the massage. I'm sure they didn't know about my plan, and they would even look at the TV from time to time when something funny happened.

I made sure to give them a little clue that I was into this. The next time they made eye contact with me, I made sure to smile and give them a 'thumb's up'. I'm sure this looked a little creepy, but I was really hoping that they would be aggressive with Tanya's massage.

I motioned to them to move their hands from her feet up to her calves, but only that high. I didn't want Tanya to get freaked out too soon. I don't even know if she was really awake. She seemed to be reacting to the massage, enjoying the touching and all, but her eyes were closed the entire time. "Hey Baby, flip onto your belly, so that we can massage your back, I instructed." Tanya complied slowly.

She moved herself away from the couch enough to lay down, feet on the ottoman still. The guys didn't waste much time moving in to massage Tanya's back. One guy was massaging her shoulders, while the other was massaging her calves and thighs. Tanya was definitely out of it. The guys looked back at me from time to time to see what my reaction would be to their various activities. I think they were starting to catch on as to what was going through my head, as their hands starting moving to different places on Tanya's body.

At first, one of the guys moved his hands up to Tanya's thighs, and then to her inner thighs, while the other guy started to work his way down Tanya's back and on to her butt, placing his hands under her shorts in order to massage Tanya's butt muscles.

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Finally I got up and walked towards these guys and pushed the envelope a little to see what would happen. I decided to help the guys out by taking Tanya's shorts and thong off. I instructed them to help me lift her hips up a bit off the couch so that I could slowly remove her clothes. I slid her shorts and panties off slow enough that Tanya didn't really notice.

They guys resumed their massage, but now on Tanya's naked bottom half. They caressed her legs and her ass, and massaged her inner thighs, it was really great to watch. I was almost panting. Just then, someone came into the room. The door opened suddenly and the third suite mate walked into the room.

The two guys froze in place, and the third guy said "what the fuck" so loud that we though that it would wake Tanya up. Luckily it didn't. She was still asleep or comatose. I walked up to the guy and explained the situation, that it was my girlfriend, and that we were all giving her a massage, and maybe more.

He was into it too and walked over to sit next to Tanya as well, finding room on the coffee table. He started, like the other two, with Tanya's feet. The other two, were by now getting pretty excited and were starting to massage Tanya's inner thighs more and more. I motioned to the first guy that he should lick his middle finger and penetrate Tanya's pussy slowly.

I emphasized the slowly part. He licked his finger, and slowly found Tanya's pussy and started to slide in. Tanya moaned but didn't wake up. The man started fingering Tanya a little bit faster now, and a little bit deeper. Tanya still didn't wake up, but she was starting to moan regularly. I walked up to her and whispered to her that we wanted her to roll over so that we could massage her front.

So Tanya rolled over some, and we assisted until she was on her back. With her bottom off, her pussy was visible to all four of us, and we were starting to get excited about the possibilities.

By now this guy was fingering Tanya enough that I figured she would wake up at any moment. I told the other two guys to massage her arms so that she didn't just wake up to some guy fingering her. They both complied and started to massage Tanya's arms, and caress her abs and waist. At the same time, I told the guy who was fingering her to start licking her pussy. He leaned his head in slowly and started to lick her labia gently and slowly, so that she didn't get startled.

Slowly he progressed enough to where Tanya began to wake up. She didn't wake up in a shock or anything, but rather started by wiggling around as she moaned, tilting her head back and releasing loud moans. When she finally did open her eyes she looked down to see that she was being eaten out by the guy that she had been flirting with. A big smile came over her face, and she moaned loudly. Tanya grabbed his head with both hands and brought it closer to her body.

The guy kept licking her pussy as Tanya moaned more and more, looking around at the other guys who were touching her arms and waist. Relief set in as all of us relaxed to know that Tanya wouldn't freak out as she woke up.

Looking at her though, I could tell that she wasn't really energetic, but rather that she was slightly lethargic. She definitely seemed to notice the men around her, as by this point they were either licking her pussy or fondling and sucking her tits.

I figured that Tanya wasn't going to be doing any strenuous activities that involved pleasuring us in this activity, rather I figured that the only thing that we could do was get off with Tanya in her semi-awakened state.

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I told the guys that they should each get a condom and gently fuck her as she lay on the couch pants-less with legs spread apart. She probably wouldn't even know.

One of the guys rushed to his room grabbed a few condoms and gave them out to the others. All at once they dropped their shorts and started getting their cocks harder by playing with themselves until the first one was ready to go. Tanya looked up at the three of them playing with their dicks and asked in a mumble, "Are all of you guys gonna fuck me?" You could barely hear the first few words, but I understood her and answered, "Yeah baby, these guys are gonna fuck you for a little while.

Just relax, you don't have to do anything." Tanya replied to me, "Is that okay with you?", to which I replied, "At this point baby, I don't think I can stop them," and smiled to her.

The first guy slipped the condom on and crawled on top of Tanya, her legs spread eagle and her pussy wet from being licked so thoroughly. He spit on his hand and lubricated the condom a bit while he slowly started to put pressure on Tanya's pussy lips with his hard cock. Tanya didn't move a muscle. Once he was in, he gently started pumping his hips back and forth as he fucked Tanya, who lay quietly on the couch.

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Tanya opened her eyes and occasionally bit her lip as she was being fucked by the kid. The first guy finished with a bang, coming into Tanya's pussy- his crotch firmly against hers with his cock laying motionless deep inside of her for a moment.

The second guy followed the first with much of the same actions, thrusting in and out of Tanya until he came. Tanya tried to open her eyes to see who exactly was fucking her, but she didn't manage to see who it was, as he finished in short time and got off of Tanya almost immediately.

The last guy put the condom on, walked up to Tanya, and before entering her pussy, asked me, "Are you sure about this?", to which I nodded, giving him the green light to proceed. This last guy was a bit more forceful on Tanya, and made a loud smacking sound with her as his pelvis met her pussy.

The slapping woke Tanya up some, but she seemed to enjoy it, as she moaned louder than she did the first two. This guy even got in close to Tanya's face, and put his arms under her back while he was delivering pump after pump of his cock into her crotch. She opened her eyes once in a while, and would look towards the guys face, but she couldn't see his face from the position his head was in.

This last guy that was fucking Tanya really got me off. It was one thing to see Tanya's beau (the kid she was attracted to) giving her some pumps, but this last guy was giving it to her pretty good, and the fact that Tanya had NO IDEA who it was felt pretty exhilarating. What set me off is that Tanya had never been this slutty, and to know that all she was really doing was spreading her legs to expose her pussy to these guys made me crazy. I made sure to get a few pictures of the moment, so that I could remember this whenever I wanted.

A strange guy lay on Tanya with his dick in her pussy. It was exhilarating to me to know that Tanya's body, her pussy especially, made those three guys so incredibly happy that night. They all got to touch her amazing body, and got to know it so well, in fact, that they got to stick their dicks inside of her. Tanya's pussy made those three guys so incredibly happy that night. To think, if Tanya had gone to bed outright, none of this would have happened.

Her pussy would have lay silent and quiet. But, with no extra effort at all, by simply spreading her legs and letting those guys' dicks into her pussy Tanya made those three guys' weekends.

Finally, I took my pants off, aroused by the past fifteen minutes of sex, and entered Tanya the same as the other men, and fucked her for a few minutes until I came into her pussy.

It was exhilarating as I stood there. Tanya was back to sleeping, and the guys were getting their clothes back on. I thought that it was hot that Tanya laid there naked having just gotten fucked by us four guys. They all quietly thanked me and walked back to their rooms. I got Tanya and got her clothes back on and put her to bed. The next morning was funny.

You'd think it would have been awkward, but the three guys all were in a good mood in the morning, and greeted Tanya with excitement. "How did you sleep?", one of the guys asked her. "Pretty good. I was exhausted.", she replied. "Yeah, we know!", one of them yelled out. The room erupted into laughter, and Tanya put her hand over her face, embarrassed.

"Don't feel embarrassed… that was awesome last night!", one of them replied. "Yeah, here, have some breakfast… I made you four sausages!" To that, Tanya laughed pretty hard and was still pretty red in the face. We all sat around and joked for a bit. It was nice to break an uncomfortable situation like that, and I'm glad we got to kid around. We asked Tanya if she would like to do it again and she replied "No.". I'm just glad that we got to do it once…