Teaching Caitlyn (and Amber) part 2

I did not understand why my niece, Caitlyn, had not called me herself. I just got off the phone with my sister, Susan. She informed me that she was going to be out of town this weekend and her eighteen year old daughter Caitlyn, would be home alone. She asked if I would mind checking in on her.

The reason I was surprised was that a few months earlier when I was giving her a driving lesson Caitlyn had seduced me and we had sex. Since then she had never missed an opportunity to fuck. If her mother was going to be gone even for a couple of hours she called me and I came over and fucked her.

She would also frequently stop by my place on her way home from work, after school, when her mother sent her to the store, and any other time she could. It had become routine; we got together at least twice a week sometimes as many as 5 or 6. I guessed that maybe she was waiting for Susan to leave before calling me. Susan has been known to change plans at the last moment, in fact she was notorious for it.

Since I had taken Caitlyn’s virginity that day, we had fucked many times. She was now an expert at giving head and we had fucked in every conceivable position and in any odd place we could think of. We’ve done it in my office, on a golf course, in a car wash, various restrooms across the city, and once we did it on a raft floating down the river in broad daylight with what had to be fifty plus drunken college kids cheering us on from the banks. I found her to be insatiable when it came to sex. She frequently had multiple orgasms and had squirted all over me a time or two.

After we had been fucking for a month or two, she had inquired about anal sex. She said it drove her crazy when I used my tongue on her ass. I knew from experience that it almost always sent her over the edge when I put a finger in there. She told me she had been watching porn with her friend Amber and they were both fascinated by the anal scenes. She told me she wanted to try it. When she told me this I wanted to turn her over right then and there and ram my cock up her ass but I wanted her to enjoy it so I explained to her that she must go into this slowly.

I went to the local toy store and got her a kit they called an “anal training kit.” It consists of butt plugs of various sizes and several dildos of varying sizes. I gave her the kit and a big bottle of lube and told her to start with the small ones and work her way up to the big ones. I also bought her a big dildo and told her that when she could take it she would be ready for me to fuck her ass.

We continued fucking every chance we got and after a week or so I actually forgot about the kit and her desire to try anal. Now two months or so later I saw an opportunity to spend some time with her and fuck all weekend. I wanted to get into her ass now. I could not wait for her to call and tell me Susan was gone and to come on over.

In the days that followed, I did see Caitlyn, and meant to ask her about the weekend but on Tuesday when I saw her she actually woke me up on her way home and we fucked but I forgot to ask. Then on Thursday evening when I went to dinner at the restaurant where she works with some friends from work she sucked me off in the bathroom but with the excitement of potentially getting caught I didn’t think to mention it. Now here it was Friday night and no word from Caitlyn. I called Susan to check in with her and she had indeed left town that morning and was now in Texas a few hundred miles away.

I put it out of my mind and went to bed. I had to go help out a friend Saturday morning and it was mid afternoon before we got through. I still had not heard from Caitlyn. I decided to go over to Susan’s and check up on her.

When I pulled into the driveway, I noticed that Caitlyn’s car was there. I wondered if maybe she was sick or possibly had been picked up by a friend. I really thought she would have called me like she had every time she had a moment alone for the past few months.

I let myself in with the spare key and there were no lights on and I could not hear anything. I guessed she was gone somewhere. I was scrolling through my contacts on my phone to find her cell number when I heard what sounded like a cat from the back of the house. This is weird I thought. I didn’t know they had gotten a cat. It sounded strange too. What kind of cat makes a sound like that?

As I made my way down the hallway, the sounds grew louder and I realized that this was not a cat; it sounded more like a person moaning. I think its Caitlyn masturbating. My cock twitched at the thought of catching her and then joining her in her bed. As I reached her open door I got a pleasant surprise.

Caitlyn’s friend, Amber, lay on her back completely naked and Caitlyn is kneeling between her legs eating her pussy. Caitlyn had the big dildo I gave her sticking out of her ass. She had a couple of fingers in Amber’s pussy and appeared to be sucking on her clit. Amber is moaning and squeezing her own nipples. From her tone I could tell she was about to cum. Caitlyn then used one of my moves to get her to cum. Just as she had Amber at the edge she slid a finger up her ass. That caused amber to scream out in pleasure. She grabbed two handfuls of Caitlyn’s hair and squeezed her head between her thighs. She appeared to go into convulsions as her whole body trembled for quite a while.

Once her orgasm subsided, she collapsed back on the bed. Caitlyn lay over on her side and kissed her cheek. It was then that they noticed me standing there. I gave them a little applause and told them “that was the most amazing, hot, and sexy thing I have ever seen!

Caitlyn just smiled at me. I think Amber would have normally been embarrassed and tried to cover up but she was too tired to move. She just lay there breathing heavily and looking at me. The dildo in Caitlyn’s ass slipped out and flopped onto the bed.

“I see you’ve been using the toys I bought you.”

“Yeah, I finally got this one up there today. Amber has been using since the first day I got it; she really loves it up her ass.”

“So how long have you two been hooking up? And why didn’t you call me when your mom left.”

“We’ve been hooking up since that day we saw your cock. We went to Amber’s house after that and were watching some porn on her laptop and started rubbing ourselves, and then each other, then we ended up eating each other out all night. I was going to call you this afternoon. I had to work last night and today I had to take my car in for service. I was going to call you when I got home but ran into Amber on the way home and then one thing led to another and well, you see what happened.”

“Amber knows we’ve been hooking up. She even helped me plan the driving lesson. It was her idea for me not to wear panties but the driving lesson part was my idea. I’ve know how to drove a manual tranny for over two years! I just pretended I couldn’t to get you over here. Amber wants to fuck you too, she’s wanted you since that time we saw your cock. She’s a virgin too!”

“Caitlyn, you weren’t supposed to tell him you little bitch!”

“You know you want it Amber. I don’t know what you’re waiting for anyway. I bet he’d fuck you right now. What guy wouldn’t; you are a hot little slut!”

Caitlyn stood up and walked over to me. She gave me a long wet kiss and said “Can you taste her pussy on me? Isn’t that some good tasting pussy?”

“It tastes as good as yours; I could lick it all night long.”

“Well there it is, go ahead and get you some.”

“I really need a shower first, I’ve been out working and need to clean up. I probably smell.”

“You smell like a man to me, it kind of turns me on. Like a boy’s locker room.”

‘I really would feel better after a shower. I could use a beer too. You got any?”

“I think mom has some, check the fridge.”

I went to the kitchen, and grabbed a beer then headed to the shower. By the time the water was running hot I had finished my beer and stepped in. I stood under the water and let it sooth my aching neck and relax me. I then cleaned up and headed to the kitchen for another beer. I popped it open and sat at the kitchen table to cool off. By the time I finished the second beer I was cooled off sufficiently and after grabbing a third I headed back to Caitlyn’s room.

I had wrapped a towel around my waist after leaving the shower, and as I walked down the hall I let it fall off leaving me completely nude. I walked in to find that the girls had taken this time to dress in some hot lingerie. Caitlyn, a true redhead is somewhat pale even though she does lay out to tan regularly. She wore a black cami and thong while Amber who is nicely tanned with jet black hair wore a white corset with white bikini panties and lace top stockings. It was kind of fitting since she was a virgin.

They were both sitting at the foot of the bed watching a video on Caitlyn’s laptop. I sat next to them and started watching. In the video there was a young girl on all fours taking it anally from a gray haired man. She was squealing and yelling and every once in a while the man would pull out so you could see the girls gaping ass. It was pretty hot and I began to get hard immediately. When the video ended Caitlyn closed her laptop and put it on the desk.

We all kind of looked at each other waiting for someone to make a move or say something. Caitlyn broke the silence and said, “We talked about it and Amber wants you to pop her cherry.”

“Yeah, I’ve been waiting because I wanted it to be special and I can’t think of a better way than to have my best friend here with me when I give it up.”

“This is going to be fun, you’re going to love this Amber. He’s gentle and knows how to do it so it won’t hurt and you’ll feel so loved,” Caitlyn assured.

I turned to Amber and told her, “I’m honored that you chose me, I won’t disappoint you.”

I leaned in and kissed her. Our tongues met and I could taste the cherry lip gloss she wore. I nibbled her earlobes and kissed her neck which really got her going. She reached over and started rubbing my cock.

“You’re so big, I’m not sure if this is going to fit,” she said

“Oh it will fit, if that big ole dildo will fit then you can take him. I didn’t think I could take him either but I did.” Caitlyn assured.

I stroked ambers hair and looked her in the eye and told her, “I’ll take it slow and if it hurts, you let me know and I’ll stop.”

“OK, I trust you.”

Caitlyn put a towel on the bed and I had Amber lay back on it. I lay on my side next to her and kissed her. As we kissed I rubbed her pert breasts and pinched her nipples a bit. She obviously liked this; I could tell by the way she kissed back when I touched her nipples. I slowly moved my hand down to her stomach rubbing it gently as I approached her mound. I teased the thin strip of hair above her pussy then cupped her camel toe in my hand. As soon as I touched her pussy she gasped and her juices flowed onto my hand. I was amazed at how quickly her juices flowed. It was instantaneous; maybe she’s a squirter I thought.

I knelt between her legs and licked her slit which brought another gasp and more juice. I lapped up her nectar as I continued to lick her slit from bottom to top. I put in a finger and found her to be extremely tight, tighter than Caitlyn was! I sucked and nibbled on her clit while working my finger in and out and she began to squirm. When I used my other hand to insert a finger in her ass she went off. She screamed out as her pussy and ass clamped down on my fingers and her thighs squeezed my head. Her whole body shook as she came and her juices leaked out around my finger. Just when I thought she was going to break my neck she went limp. I pulled my fingers out and slid up her body to insert them in her mouth. She sucked her juices off my fingers and I gave her a kiss.

I lay on top of her with my weight supported by my elbows and gently kissed around her neck, ears and tits. I looked over at Caitlyn who had been holding Amber’s hand and she had a big smile on her face. She leaned in and kissed me, then kissed Amber and then we all kissed each other with our three tongues dancing together.

“Are you ready to become a woman?” Caitlyn asked.

“Yes, I want that big cock deep inside me and I want him to come in me.”

With Caitlyn still holding Amber’s hand and smiling up at me I put the head of my cock at the entrance to Amber’s pussy and rubbed it up and down her slit. Once I had it pretty well covered in her juices I eased it in a little. I held there for a few seconds as I kissed her again. As we kissed I gently eased in little by little until I felt her barrier. I broke the kiss and told her that she would feel a little pain when I went the rest of the way in but I would stop and let it subside. I told her to let me know when to keep going.

A slightly scared looking Amber shook her head OK and Caitlyn assured her she would be OK and she would love it. Her worry faded and she smiled at us. I gave a quick thrust and after breaking her cherry slipped the rest of the way in. She winced and teared up slightly and I held still.

Caitlyn stroked her hair and said, “OK honey, you’re not a virgin any more. Now it’s time to feel what it’s like to be fucked like a woman. Just take your time and let him know when to keep going. You’re gonna love it I promise.

We lay there while Amber adjusted to the full feeling of having a cock inside her and I kissed her neck and nibbled her earlobes. Before long she started moving under me, trying to get me in deeper. I took her queue and slowly pulled almost all the way out then slid slowly back in. She sighed as I slowly slid deep in and out. Her pussy was so tight it almost hurt at first but as I slowly worked myself in and out of her she stretched and I found it easier to go in her.

I slowly picked up the pace and she wrapped her arms around me. Before long I was pounding in and out of her. I could feel myself bottom out with each stroke. I was straining to keep from coming as her soft wet pussy massaged my cock. The feeling was exquisite. She began to beg me to fuck her deeper and harder as she dug her nails in my back. My balls were teasing her ass as they slapped against her on each stroke. I looked over at Caitlyn who was staring in amazement at her friend being fucked.

Amber reached out and squeezed Caitlyn’s hand as her orgasm hit. She wrapped her legs around me and used her free hand to grab my ass and try to force me in deeper. I pushed in as deep as I could go and spilled my seed deep inside her. I held my cock deep inside her as I pumped the biggest load ever into her. I couldn’t believe how hard I came and had to admit that Amber’s pussy felt even better than Caitlyn’s.

I slid my cock out of Amber and lay next to her. She rolled on her side nestling her head on my shoulder and started rubbing my chest. Caitlyn lay on my other side with her head on my shoulder and held my softening cock in her little hand. We eventually drifted off to sleep.

I awoke to Amber’s tongue in my ear and her hand on my cock. I turned to her and gave her a long passionate kiss. I reached down to her slit and found it kind of messy. A mix of our combined cum with a little blood was starting to dry. We left Caitlyn sleeping and went to the shower to clean up.

We stood under the warm water kissing as she gently stroked my cock and I pinched her nipples. She took the soap and washed my entire body not missing an inch. Her little finger even found its way up my ass as she was soaping me up. I returned the favor and soaped her up completely. Her erect nipples, smooth ass, and sweet little pussy looked and felt so good to the touch I was soon painfully hard again. I turned her around and rubbed my cock up and down her slit. As I placed the head in her hole she stopped me.

‘I’m a little sore there from before. But there’s another hole you can use.”

I didn’t need to be told twice. I soaped up my cock and bent her over some so that she put her hands against the wall to brace herself. I pressed against her puckered hole and slid all the way in with very little resistance. I expected her to be almost impossible to penetrate back there since her pussy was so tight but it was about the same. She sighed deeply as I bottomed out and my pubes pressed against her.

“Ohhh, that feels so good,” she purred.

I started a slow steady rhythm sliding in and out of her and reached around to grab her tits. She was pushing back against me on each thrust and her hand was busy stroking her clit. Our tempo gradually grew until I was pounding her ass like a jack hammer. By balls slapped her pussy on each stroke and our wet soapy bodies made an obscene slapping sound. She wailed and screamed as she came hard and squeezed my cock with her anal muscles. Her whole body trembled as I pulled out completely.

It was then that I felt Caitlyn behind me. All the noise woke her and she joined us to clean up. We both soaped her up and cleaned every inch of her body as we took turns kissing each other and the girls stroked my cock and cupped my balls. When we finished our shower we dried off and went back to Caitlyn’s bed.

As we all piled on the bed Caitlyn said, “I want what she just got. I it’s time to pop my anal cherry.”

“Seeing how it’s the only hole left on you two for me to break in I definitely intend to go there,” I said.

‘Sorry big guy but you weren’t the first guy to do my ass,” Amber replied. “I’ve been fucked there by three guys, I didn’t want to give up my pussy so I let them have my ass.”

“No wonder you were able to take it so hard.”

“I don’t know if I can take a pounding like that, it is my first time after all. Promise you’ll be gentle?” Caitlyn asked.

“You know I will,” I replied and gave her a kiss which started a half hour of kissing, licking, and sucking between the three of us. I was sucking the girls, they were sucking me, they were sucking each other, we all had our mouths and hands busy touching and licking whatever parts were closest at the time.

We ended up with Amber on her back being eaten like they were when I arrived and me behind Caitlyn who was on all fours eating her ass and cunt. I positioned myself behind Caitlyn and rubbed my cock up and down her slit. I decided to go for her pussy first and slid in to the hilt. I fucked her deeply and reached around to pinch her nipples.

Once I had her worked up real good I put the bead of my cock against her rosebud and pushed. After a bit of resistance my head popped in and I sunk in an inch or two. Caitlyn squealed with delight as I reached around and found her clit. I rubbed it until I felt her pushing back against my cock trying to get more of it in her. I slowly pushed the rest of my cock in until I was balls deep, then I pulled almost all the way out and plunged back in. I could feel her squeezing my cock with her ass muscles then relaxing them and letting me move again. I increased my tempo until I was slamming into her as hard as or harder than I had Amber in the shower. My balls were slapping her pussy on each stroke and I was using two fingers to massage her clit.

When her orgasm hit it was a big one, she squeezed my cock so hard it hurt and she squirted all over the bed. When it was over I pulled out and her ass gaped wide open. I wanked my cock a little and squirted my load in her open hole.

I sat back and watched as she spun around into a sixty nine with Amber and continued to devour her pussy. “Mmmmmmmmmmmmmmmm, creampie! Amber exclaimed as she began to lick up all the cum that was leaking from Caitlyn’s asshole and running down onto her pussy. Soon she had licked her clean and was sucking her asshole to try to get every bit of cum out.

We spent the rest of that night and all day Sunday in bed with the exception of a couple of showers and a trip to get Chinese takeout. We had changed the sheets several times since Caitlyn kept squirting on the sheets and the whole room smelled like pussy. I have to admit I felt like a king as we went to sleep Sunday night with me in between my two recently deflowered princesses. I remember wondering if I was going to be able to satisfy them both and if so for how long?