I don’t even know how I ended up on the bed at this point, but he is lubing his fingers and begins to lube and finger my ass…  First, one finger.  I can feel my sphincter clench.  It feels – oddly erotic.  It must be the motions Leo is doing with his finger.  He adds a finger.  OMG.  This hurts.  I have to ask how many fingers he has in me because if feels like he might have a whole fist in me – not that I know what that would really feel like as I have never done that!  He says two fingers.  Somehow, that is reassuring and I feel my tight little bung hole begin to relax and enjoy this.  These new sensations are triggering and …
I like it.  (I liked it so much I am getting turned on writing this…)
Leo gets my ass very lubed and ready and I get up on all 4s with my ass wiggling in the air.  Yes!  Yes!  Oh, Yes!  I want his cock in my ass!  Gently, he pushes his big cock head into my tight, tight ass.  Oh!  Oh!  Ow!  Ohhhh….   A rush comes over me.  It feels gooooooood…  The only thing I have ever had in my ass before this was a little “probe” – about the size of a large index finger – and I did not like it.  It just made me feel full and it hurt like hell to move it.  But this.  This cock is warm and soft – no, Leo is still hard, but his cock feels good – smooth – against my tight ass.  He pushes a little deeper and I scream and moan all at the same time…  Soon, he is pumping my as with his hard dick – Fucking my virgin ass!  And I am LOVING every minute of it!  Oh, don’t get me wrong – it still hurts a little – but the sensations are exciting at the same time!  I tell Leo I like that he was the one to “pop my anal cherry.”
He slows his thrusting.  I interrupt him before he can say anything, “You’re fucking my virgin ass! And, I’m LOVING it!”  Don’t stop!  He begins to fuck my tight ass some more…  (Leo did not know my ass had never been fucked before…)
He stops and kisses me all over.  He touches my whole body – every inch of my skin, every nerve ending fires – his hands, calm, and sooth, and yet, excite, me.  As I ponder, “Is this really happening? And do I REALLY love anal?”  Yes!  Yes I do!!!!!!  We drink some more wine.  He teases me and asks if I’m glad he came here and that we are doing this.  He has some Dom tendencies – which I like and would love to explore more as I have some Sub tendencies that could meld nicely…
We experiment with some toys up my ass and I masturbate my pussy and cum for Leo.  He wants to DP me with toys and I am so into trying new things I agree to it!  BUT!  Not just NO! STOP!  But OH FUCK NO!   This pain is more than I can stand.  THIS is NOT pleasurable.  It hurts to move, it hurts to move either toy.  We stop that. 
Leo tenderly touches me some more…  His hands are gooooood.  My body and brain are dazed with these new sensations.  He sits on a kitchen chair and tells me he wants me to ride him with his dick in my ass…  This is all so new to me, and I am enjoying it so much, I back my ass up onto his dick and begin to bounce…  Fuck!  I love it!  Suddenly, I am overwhelmed with exhilaration!  I am not having a physical orgasm, but my brain just exploded…  I move off his cock and fall on the bed – I do not know if I am laughing or crying.  I am overjoyed at the experience.  Reveling in my own sexuality.  I think he is happy to share in this moment with me as he kneels on the bed, next to me, and begins to jack off over my tits.  Suddenly, a spurt of cum flies past my opposite shoulder as the rest falls on my big, soft boobs.  It’s creamy warmth like a blanket of possession lying lightly upon my chest.  Leo looked down at me and I took a finger and scooped up his hot creaminess and licked it off my finger…  He bent down and kissed me… 
We finished the wine and talked and he played with my ass some more – Damn!  Why do I have to like it so much?  Leo is the master of my ass, that is for sure.  I’ll be back this way in a few months… maybe we can explore some more of dom/sub fantasies?  I really would like to be tied up, maybe even blindfolded, so he can play and tease me – making me drip and BEG!  If it’s anything like this night was… I’m sure I’d LUV it! 

We end up back at the hotel I go to my room and he goes back to his to get a few things and comes back.  I threw my keys and purse on the table and headed to the restroom.  I kicked off my shoes and my jeans and went back out with only my leopard print thong on the bottom.  I pour us a couple of glasses of wine.  There’s a knock on the door, I let him in and I wander over to the window so he gets a nice view of my ass.  He grabs the wine and comes up behind me; I try to turn but he won’t let me – he is admiring the view…  He presses against me and I can feel his hard cock, pushing into my buttocks.  I am so horny and turned on he could take me, right there.  But no.  He whispers that he wants me to suck his cock.  I smile and hurriedly unbuckle his belt and get his pants off of him.  I nearly push him onto the bed as I grab a pillow to kneel upon.   His ass is nearly on the edge of the bed, just how I like it as I kneel between his knees.  I smile up at Leo.  He is propped up on his elbows – watching me.  His cock is fantastic!  So HARD!  My mouth and tongue are making love to his cock – sucking the head in and pressing my tongue at the frenulum and sucking him deeper, slowly.  Leo’s cock fits almost perfectly into my mouth, whole.  I can deep throat him, yet he tickles my tonsils and I gag a little bit.  My head begins to bob up and down, furiously tasting and sucking this magnificent dick.  And Leo tells me I’m a good cock-sucker and that just makes me want to keep going!  Oh yes!  My tongue slides down the back of his shaft as I suck his balls into my warm, wet mouth as my hand strokes his shaft…  I can feel my pussy, dripping wet as I continue to suck Leo.  He then tells me he knows I want his cock in my ass.  WHAT?!  I kind of ignore it as I do not do anal.  He keeps telling that he knows how badly I want his cock in my ass…  I keep sucking this hard, gorgeous cock.  He says he knows I want him to fuck my ass.  What?  What is he saying?  I’ve had a lot of wine and my inhibitions are down and he wants to do WHAT? 

It's Thursday morning, and I am in class for work.  I look at my phone and stare at Leo's number. that I have entered for texting.  Is it too early to text him?  I smile to myself.  Soon, he texts me good morning.  Phew.  Why do I suddenly feel like a ***** girl?  I’m nervous.  This isn’t like me.  I don’t do this sort of thing.  I’m in a minor panic mode as I try to allow myself to be more open, less uptight.  He’s going to drive down.  He sends a text that he has crossed the border.  I really am going to do this.  I feel myself blush with anticipation. 
When class ends, I rush back to the hotel.  I pour myself a glass of wine. I put on the sexiest blouse I had brought with me, which is not very sexy as I had not packed for anything like this.  It is light gray silk, with a little sheer lace across the shoulders.   I have on a nude color, smooth bra.  Nothing fancy but it does make my breasts look good!  I put the cork back in the wine and head out the door.  I am so nervous and excited that I am physically shaking. 
We’ve agreed to meet at a local sports bar about quarter mile from the hotel.  I walk in and smile at the hostess and say that I am looking for my friend.  He is sitting at the bar and nods to me.  I walk over and we kiss cheeks and introduce ourselves.  We decide to sit in the lounge on the comfy sofas.  We each sit on a different sofa at a 90 degree angle to each other.  This is fine with me at this point, as I am quivering, and not in a good way, yet. 
Leo notices that I am anything but calm and we order me a glass of wine.  I take a few deep breaths and we chat about life in general and how both of us have ended up, here.  I order another glass of wine and am beginning to relax.  We share a plate of nachos. The sexual tension is rising.  Yet, we still have not touched. 
We finish our food and drinks and leave.  Leo had walked to the bar; so I drove us both back to the hotel.  All I remember is starting the car and that we didn't even touch each other in the car! 
 

I could hardly wait to log in on Wednesday night.  I was VERY horny from thoughts, nearly all day long, about my new friend.  I'll call him Leo.  I plug in my HD cam and set it up for a sexy side glancing view of my tits, under my nightgown.  Being on cam is immensely exciting.  I am an exhibitionist, at heart.  I turn on my cam.  The chat roll moves quickly and I exchange pleasantries and fend off requests to show more.  I like to go slowly.  Leo is logged in, too, and we chat a little bit about our day.  As I begin to relax, I also become more and more excited.  I allow my nightgown to slip aside and show my tits.  Nice nipples.  They get stiff when I’m horned up and there is no doubt that is how I am feeling, tonight.  I do love the attention.  Especially the attention from Leo.

Our chat is full of sexual inuendos by this point, and we end up in a private chat box, with both of us on cam.  Our conversation is full of sexual tension.  Come to find out, he is about 2.5 hour drive away from where I am staying.  Hmmmm.  That's not too far, I think.  (WHAT AM I THINKING!  OMG!  THIS IS SO NOT LIKE ME!)  He is seeing my big tits, up close and personal, and I am seeing his tshirt and jeans.  Ok.  He’s new.  Maybe a little shy?  (Please get your cock out Leo!  I scream in my head...)  Our conversation is getting me very horny… as we talk about what we might like to do to each other should we close the distance between us.  For some reason, I thought he lived in another region; knowing he was this close was extremely arousing…(and OMG!  What AM I thinking!)

I am horny as fuck now and I move my cam for a full on view of my pretty, tight, smooooooth pussy.  I am so horny, I am touching.  I wanna see Leo’s cock SO badly…  As we discuss the possibility of his visiting me the next night… My mind is reeling!  Oh, my God!  Is this really happening?  Or is he teasing me?  Or?????  I am playing with my clit and fingering my wet cunt, now...  I didn’t think he could watch my pussy for too long without getting his cock out and I was right…  Mmmmm, his cock is not large, but not small, either  – and shaped very nicely with a large head.  It is a very sensual cock and I can feel my pussy begin to drip with anticipation.  I grab my toys and pump my dildo in and out of my pussy and rub my clit until I cum… again and again.  My pussy is clenching and *****.  I moan.  Louder and louder each time!  Leo is clearly turned on as he strokes his cock – he has so much control and I find that even more stimulating!  I am in the throes of multiple orgasmic bliss and squirt a little!  Yes!  The ultimate release!  I giggle a little as the feeling is so intense and gratifying … Did he see it?  Did he see me squirt?  And.  Oh, my god!  That cock!  I need to be on my knees worshiping it!  He is SO hard and … he puts his dick away.  What?  Hmmmmm.  I’d like to see him cum.  Darn it. 

We continue our conversation about his needing to go for a drive anyways and the possibility of meeting up the next day and we exchange numbers so we can text the about the logistics.  I tell him I want to see him cum; he teases me some more and tells me to get a good night’s sleep.  I don’t get to see him cum.  What a TEASE! (Not that I mind…too much!)

It began on my business trip, last week... It was late, Tuesday night.  I was feeling frisky and logged into YouViewToo.  I enjoy watching and observing and chatting, and yes, occassionally masturbating - especially when I am in a hotel room, all alone.  It was a relatively quiet night.  One of my female friends put in a good word about the New Guy.  (New to me, anyways)  No, he was not on cam. He had a way of chatting that I found very intriguing and attractive.  Honest.  Flirtatious.  I quickly checked his profile.  Oh wow!  I liked what I read and I liked what I saw!  He has one soft core picture posted - his very hard cock in some tight undies.  My mind began to wander, as did my fingers...  Eagerly, I joined the chat roll.  We exchanged pleasantries and he bites at my double entendre' and makes me grin.  THIS could be fun!  And although, I am enjoying this new conversation, immensely, it is quite late and I need to go to bed.  I say my good nights, log off, close my eyes and rub my clit and finger fuck my pussy as I fantasize about the possibilities with my new chat friend...  I cum fairly quickly.  A nice release, nothing major, but a good O, nonetheless.  Ahhhhh, I can sleep well, now.  Maybe...