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.
