My First Time Fantasy

Well, since I'm being honest, I need to tell you my deepest fantasy...

I was involved with a woman named Jodi. It was a brief relationship which we both wanted to last but certain outside forces put an end to that. We still text from time to time. The sex life we had is still a topic of conversation for us. One thing she wants to do, if/when we hook up again, is peg me. I've been thinking about it so much that I even picked out the strap-on for her to use. She has even asked me to save my ass just for her. During a recent conversation I asked her what I'm to do if I like it when she finally takes my ass the way I've taken her's so many times before. Her answer, "We'll find someone to join us."

So, now I find myself in a quandry. I've sucked your cock several times... God I love how empowering and degrading it is for me... And I find myself wanting to know what it's like to have you in my ass. Seeing that in writing makes me blush from a combination of embarrassment, shyness, fear, and need. I do want to save it for Jodi but my need to have you be the first is overpowering.

This day starts out like any of our previous meetings. I get a text from you asking if I want to hang out for a while. Having no other plans I'm up for it. Aside from our first call and meeting, we never plan what we're going to do. Sometimes I suck you off, or you suck me off, or the wickedly hot 69 we did a week before, and sometimes we just have a beer and watch a game and nothing sexual happens.

Today, I have the urge and I wouldn't know how to bring it up without being face to face. I start packing an overnight bag, which I've brought along every time and always leave it in my car, but it's there just in case you want to have me spend the night as you've admitted to wanting at some point. I decide to take a shower so I'm nice and clean for you. When I get out of the shower, I convince myself that I should make use of a butt plug that I bought for one of my ex loves when she wanted me to take her anal cherry. I've used it on myself a few times. It's a harder plastic vibrating one, not very big when compared to a cock but it makes it's presence known. I use a good amount of lube and slowly work it into my ass. I plug in the battery pack and turn it on to make sure it's working. The vibration makes my knees weak and my anus twitch. I put on satin panties you gave me and my I start getting an erection from all the sensations. I finish dressing, battery pack still plugged in with the control in my pocket, and I head out.

At every stop sign and traffic light I buzz the vibrator for a second or two. This is keeping me hard. I can feel the wet spot forming on the panties. My cock is absolutely aching for relief. Fuck, this is going to be a long drive...

I call you when I'm close to your place and tell you what's going on. Hearing about the butt plug and wanting you to fuck me makes you let out a deep, "Oh, yes". You say you'll leave the door unlocked and that I should come straight to your bedroom.

I arrive 2 minutes later and waste no time in doing what you said. As I enter the room, I see you sitting naked on the edge of the bed. I strip off my clothes as quickly as possible, leaving the panties on. You tell me to lie on the bed, put a pillow under my butt to give you access to the plug. Then you kneel between my legs and slide the panties aside, exposing my dripping cock and giving you a full view of my ass. You grab the base of the plug and slowly pull it. The feel of it stretching my hole makes me moan. You pull it almost all the way out and slowly push it back in until only the base is left. Again I moan, then I ask you to keep doing it. I can feel the heat growing in my face from blushing at asking you to fuck me with that toy. You slowly beging the first violation of my ass, both of us knowing it will soon be replaced by your cock.

It's not the most comfortable feeling but nt unpleasant. Definitely a little painful. I give you the control and don't need to give you any hints on what I'm looking for. You start with the slowest constant buzz setting. This makes me moan a little. The vibration goes right to my cock and makes me drip. Seeing this, you immediately take the head into your mouth, not wanting to waste a drop. I can't stop my hips from bucking and fucking you mouth for a few seconds. You stop and tell me in a stern voice, "That will be remembered, cunt". The words and tone of your voice make my heart sink, my cock ache and a large spurt of pre-cum flows out... Again the degrading makes me want this even more.

You go back to sucking the head of my cock, almost angrily slurping up the fluid. You go through all the settings on the vibrator, watching my face and listening to the sounds I make at each setting. When you hit the one that buzzes hard, stops, and starts, almost like a hard "thump, thump, thump", I gasp. This is what it will be from here on. "Oh, shit! Yes!", I yell. You pick up the pace only slightly, but with the combination of the toy being pushed all the way in and pulled all the way out, the thumping vibration, you sucking my cock, the satin panties sliding across my ass every time I move, and knowing I'm giving myself to you, is way too much... I start cumming in your mouth. You let me finish but soon as the last drop comes out, you crawl onto me, straddling my chest and pinning my arms under you... I'm helpless to move... You force your cock into my mouth and dribble my own cum onto my face while fucking my mouth... I'm freaking out! How the fuck can this be happening?!? Why am I so enjoying this?!? God I hope you cum and quick... You don't... Instead, you pull out, scrape up my own cum and feed it to me. More humiliation... and I'm loving it.

You finally let me up and we talk to calm things down. You apologize, kind of, to let me know it was just from being caught up in the act. I don't even give it a second thought and tell you, "It's ok. I'm starting to fall heavily into what we're doing. It was a huge turn on... I think I'm regretting not trying this sooner". And, with the air clear, I go to take a shower to get myself clean. I come back to bed and you go to shower too. When you come back, I'm sound asleep but I feel you behind me and you hold me while we sleep.

I awake and see it's nearly sundown. I know you're awake as I feel your hands touching me all over, with most of your attention on my butt. "What did you do to me? You wore me out, you pick", I joke. "Nothing you weren't begging for, slut", you shoot back. Even though I laugh, there's an equal amount of truth and sting in your comment. It was all true, and I've never been more content.

The thought only lingers for a second before I'm aware of your finger spreading some lube on my hole. I flinch at first from the coldness of it but that quickly passes. Then I feel your thick finger sliding into me. It feels much better than the toy, though the wide part made this a bit easier. You're gentle about it at first, then you start moving it in circles, trying to stretch me open a little. I have to catch my breath as i feel you pull out and begin forcing 2 fingers into my asshole. I gasp at the pain of your thick fingers spreading me. It does sting more than the widest part of the toym without the relief, except for the momentary breaks when you pull out, only to push back in again.

You finger my ass for a good 10 minutes, although I'm so lost in everything I have no concept of time. When you pull out for the last time, I feel a strange emptyness. I know what's coming, having fucked many women exactly like this, and the fear of it has me shaking. Even more telling for my anticipation is my hips rocking back to present myself to you... For you!

Before you enter me, I grab my phone and ask you a favor. "I want to record a little message to send someone, Jodi. You can phrase it any way you want, but just let her know what's about to happen and there will be another video showing the outcome. This is important to me." You hesitate but finally agree. You start off with the camera facing yourself and say, "Hello, Jodi. You don't know me but you know who is sending this, and it was recorded on his phone. He just wanted you to see this and he hopes the three of us can play like this very soon", then you point the camera at my well lubed, and ready ass. The camera catches my moans and gasps of pain as you start pushing into my ass. I'm doing all I can to push back and help. I let out a deep "Ooohhh" as the head is fully in. I can hear you say to the camera, "Oh, look at that. The head is in and I'm about to push more in. I'm shutting the camera off when we get going. Just be waiting for the next video". And with that, you push more and let me get used to it, over and over until you bottom out. You take video of the first few strokes, I'm moaning like a slut on the video, and hand the phone back. Somewhere in all of that I was able to function enough to send the video.

So... Now we're really doing this... I'm getting my ass fucked by the only cock I've ever considered, wanted actually, to do this. My mind is racing with thoughts of how good it feels but wanthing the underlying pain to stop, not wanting this to end but wanting you to cum, if this will happen again or how I will feel if it doesn't, what if Jodi sees the video and want nothing to do with me...

Even on our sides you're picking up more speed while going deeper. I ask you to slow down but keep going deep. I'm loving the feel of the head almost coming out, then you grinding against me, making me feel every inch of your beautiful, thick cock. You grab my hair with one hand and pull my head back, the other grabs my hip and pulls my ass harder to you. I can hear you breathing harder. You again start talking at me. "Oh, yes! So fucking tight! You like this, don't you, cunt." I can only moan a low, "Yes. Fuck me. Use me. Use my ass like a cunt and cum in me. I want to be your little cum slut cunt". This time, the words have more impact on you. You pick up speed and keep going as deep as you can. I look back and can see from the expression on your face that you're about to cum. You let out a loud groan and I feel your cock pumping in my ass, along with the heat from all that cum. You pull my head back to you and kiss my neck, letting me know you're done.

We lie like this for a minute, your hard cock buried in my ass. I start the camera on my phone and hand it to you. You point it at my ass and slowly pull out, then you move down to get a good shot at my now gaping hole dripping cum. "Look, Jodi. I fucked him like he's fucked you. Now... When we play together you know it will be all holes open for all of us. So, what's it going to be?", all while filming cum dripping from my ass. You stop recording and hand the phone to me. I quickly send the video.

I go and clean up again. When I come back, I hear my phone ring. Looking at the screen I smile and say, "It's Jodi!"