Shoehorn Please?

Soooo….

We decided that after the most successful second meeting that we wanted to see if this newfound attraction (on my part apparently…he never had a doubt) extended beyond a good old fashioned make-out session, but how to make it happen?  Our work schedules don't exactly mesh quite right, and his required time at work is almost directly opposite to my own.  What's a little complication like employment and livelihood when it comes to potentially rockin' good sex??  For us…the answer seems to be, "What complications"?

We had been burning up the internet airways for almost two weeks after that fateful coffee kiss 'date' and we were both really beginning to feel the strain that a mutual attraction inspires when you can't get your hands on said object of your desire…there was an admission of taking matters into his own hands several times lest his head explode, and I guess in a manner of speaking, he did indeed explode.  LOL!  Anyhow—the affair gods took pity upon me and I had an afternoon open up.  Sent him an email explaining what happened and asked if he could find an availability for us to make things happen.

I'm going to have to remember to copy/paste our exchanges for future blogging reference, but what follows is a fairly adequate representation of our exchanges prior to actually meeting at the hotel:

Tripp: Just out of curiosity when would the couple of hours be today?  I know I'm bad and if it's rushing it we should wait, but the wait is killing me –

Me:  When would work for you...I can potentially make it for any couple of hours between now or whatever few hour combination...but I would have to be walking out no later than 4...

Tripp:  Looking for a place now.  I know the check in time at the ******** is 3, so that won't work.  I'm going to call the ***** Inn to see what time check in is and I'll get back to you in a bit.

Me: Sounds like a plan…even though, I didn't exactly plan for this, so if my underwear isn't particularly sexy and  doesn't match, it won't be a deal-breaker I hope. ;-P

Tripp:  Oh no! I don't know if MY boxers will be a deal-breaker though. (God—I am soo embarrassed now!)

Me:  Oh now you HAVE to tell me…affair-code requires it of you.

Tripp:  Well, you'll find out anyhow…so here goes…but let me first defend myself by saying I had no idea we were going to get together today, and well…I just grabbed the first pair of boxers I laid my hands on…

Me:  Well, at least it's not that you're going commando (although that would be fine…one less article of clothing between me and you)…spill the beans…what's the drama??

Tripp:  I can't believe I am actually feeling redness creep into my cheeks!!!  It's not exactly the first impression I want to be leaving you know…

Me:  Just tell me already…jeeez!!

Tripp:  Fine.  I am sporting Superman boxers today.

Me: !!!!  Too funny!!

Tripp:  Great…you're going to point and laugh. :-P

Me:  No I won't.  Well, I won't point anyhow.  I gotta say though, that's quite an impression you have to live up to now…"Superman"?? 

Tripp:  You'll find out later. ;-)

Me:  okay—but if you wear a cape, have an aversion to kryptonite, and can leap buildings in a single bound….we're through. ;-)

The morning went on unbearably slow with its usual little hiccups and problems that seem to be all the more problematic when you have a "first time fucking" encounter on the brain.  All the anticipation, the nerves, the excitement (amplified by increasingly racier email exchanges throughout the morning hours…oh yeah, I so won)…until it was finally (omg!! It's time) time to meet.

I had to drive around the block a few times to get parking (and praying the whole time no one hits me because I'd have no reasonable explanation for being downtown) which only amplified my nerves and caused me to be a little pissy with him when he sent me a message asking where I was.  I hate traffic.  Just sayin'. 

Anyhow, I found a parking place, and Tripp had, by this time, emailed me the room number.  I chose to ignore the rest of his messages and just went up to the room.  Once I stepped off the elevator and determined the correct direction of the room, I sent a response to the "where are you?" message with…"Could you open the door please?", and proceeded to stand just outside of the peephole view. (No—I never do anything simply…shut up). 

I heard the distinctive clickety click of a hotel door opening and once I sensed it was open enough, I jumped in front of him (startling him…yay!) and said, "Surprise!"

Well, he surprised me back by snatching me out of the hallway and shoving the door closed with our bodies…kissing me while doing so…and kissing while we managed to remove one and other's shirts (note: button down shirts are a great thing to wear when you don't want to stop kissing while disrobing…just sayin').  When he stops long enough to pull his t-shirt off, he looks down at my bra (which happened to be very red and very lacy), he finally commented, "Cute" and proceeded to start kissing me a bit more aggressively then.

That's okay—I can do and be aggressive myself, so it was game on as far as I was concerned.  I draped one arm around his neck to pull him in harder, and proceeded to unbutton, unzip, and drop his pants with the other in a rather rapid manner.  Then, without missing a beat, switched arms and reached up into his boxers…and…

OMG!

I mean seriously…Oh. My. God.  I was stunned into silence and pulled back from our kiss slowly and quite an incredulous look on my face, I am sure.

Tripp:  What?!? (slight worry furrow on his brow)

Me: You…uh…I mean…uhm…just that…well…oh my God!

Tripp:  Breathe.  Find your words babe. (it's common for me to "lose" them when I am shocked or close to/in the midst or an orgasm…this time, was shock).

Deep breath.

Another deep, deep breath.

Tripp:  You okay??

Me: Uhhhm…I think I'll be okay.  Sweetheart, you can wear those Superman boxers whenever you like…they are quite the understatement.  Superman indeed!

Tripp: What?? I don't understand.

Me: Jesus—you're huge!  Please tell me that's not the first time you've heard THAT!  I've seen more than one or two in my days and you are, to date, quite the largest I have seen, touched, and eventually fucked.

Tripp: I can't say I have honestly.  It's only been my wife for the last 16 years.  I guess she's used to it?

Me: Wait…what?? WHAT?!?!?! Christ…un-fucking believable!!  You've never cheated before??  What the hell did you do this past year?? Just stop looking?? What happened on AM??  I can't be the only one who you've met!!!  I'm going to be the one to take your 'affair cherry'??  Damn it, Tripp!! You shou…(he interrupted my tirade by taking my face in his hands and kissing me again….)

Tripp:  I should what Jane??  Do this? (kisses my neck) Or this? (takes a nipple into his mouth) Or this? (begins to rub my clit)…

Me: (nodding my head against his kisses…talking through our kisses) You should *gasp* have t-t-told me…

Tripp: Told you what?  That I met a couple other women, but had no interest in fucking them?  (kisses) That I hid my profile for the better part of the year?? (nipple pinches) That I couldn't stop thinking about you since we got back in touch? (moving me towards the bedroom of the suite)

Me: (putting my arms out, blocking us from entering) I'm serious now.  No harm, no foul.  Are you sure you want to do this?

Tripp:  Yes!  I wouldn't be here if I didn't!

I drop my arms and we kiss our way to the bed, me falling backwards and pulling him down with me.  We proceeded to kiss, bite, lick, and suck any and all manner of each others bodies until we had reached to point of no return and, this is it folks, we're going to fuck.  Woohoo!  I take the opportunity to ask him once more before we do the deed if he was sure.  I figure it's only fair to give him the option to choose to opt out or go for it.  The onus of responsibility for any guilt he might feel would rest squarely on his own shoulders. 

Needless to say, he chose to fuck.

I will be the first to say, I was way more than ready to do it…he properly administered to me in such a way that I would have probably cried had he denied me a thorough fucking.  I was wet and I was wanting.

Him. 

Right.

The. Fuck.

Now.

He patted my behind in such a way and said, "Turn over—I want to do you doggy first."  All right baby—that's what I am talking about….except…

I have been told by others that I was 'tight' and really didn't think much of it simply because it hasn't been a problem, which really made me think that it was said out of the need to say something when fucking.  I guess I believe them now. 

He pushed, he adjusted me, he adjusted himself, he pushed again…nothing.  Unbelievably, he could not get his raging hard on into my well lubricated pussy.  What the hell, over!  I couldn't believe we couldn't get this one thing right!!  I asked him if he ever had this problem before…he shook his head no and said, "You're just so tight".  Well fuck this…if that didn't work (and surely he must be doing something wrong…) I was going to make it happen then.

I had him lay on his back and I straddled him…rubbing my wetness all along his shaft just to be certain there would be no further issues.  I almost brought myself to orgasm with all that rubbing, but managed to wait it out.  I reached between us and grabbed him, set him at the correct angle…and I have to say here, I have NEVER had a problem just slipping a man in hand-free when I am on top like this…I pushed, I adjusted him, I adjusted me, I pushed again….and nothing.  I could not fit him in me.

This was serious business folks…but, in my usual manner of keeping things light and diffusing the building tension, I simply asked, "Do you happen to have a shoehorn handy?" 

Needless to say, the ridiculousness of the question and the mental image it produced had us both laughing to near tears and definitely eased the stress.  We decided, for the time being, to go for simple missionary, and even then, we had to adjust.  The only way we managed to get him is was by my putting my feet on his chest while he entered, once he was in though…all I have to say is…wow!  The fact that I was being rubbed all the right ways on the inside and the outside—I can honestly say I have never experienced anything quite like it before. 

It wasn't long before the moans and groans turned into 'oh fuck' and 'oh God' to me stating how close I was and 'ohmygodIamcumming' to his 'oh yeah' and 'oh babe' to his own "I'm going to cum" to me looking him in the eye and telling him to cum for me, which apparently had the desired effect because he just says 'yes' over and over again until he nearly collapses on me in a spent heap…I wrap my legs around his back and just hug him to me, not wanting him to pull out and take that wonderful fullness from within me.  So we relax…and he stays in me.  And we chat…and he stays in me.  And we start to kiss…and he is still in me. 

Some more kissing….and now he's starting to move in little in and outs…and I feel him getting hard again…

And so it begins again.  Game on baby!