Last Week with Hillary

So, I’m in a pissy mood today – Maddie sent me a ridiculous email and then I was supposed to have a date with Sally that she’s had to cancel because her kid is sick.  I really want to vent about it all but…I don’t think my readers want to hear me bitch and moan so I’ll save it for later.  Or, maybe I’ll calm down and not even bother you with it all.  In any case, I thought I’d share a hot story!

My friend Hillary, whom I first wrote about here: Meeting Hillary, offered to drive over to my place last week to see me.  Of course I accepted because, well, she’s pretty hot and it was totally easy for me. I didn’t have to drive anywhere and I didn’t have to fork out money for a hotel room that we’d only be using for an hour or two.  I did have some reservations though, mainly because Hillary seems a little needy and I’m worried that she’s getting too into me.  I know that sounds conceited but I’m just being honest – I really do see it that way.  And, as one of my astute readers pointed out in her comment on another post here the other day, Hillary is likely seeking the validation that she doesn’t get at home from her husband.  I get that and I’m ok with it up to a point but I hate feeling like I HAVE to email or txt her every single day, you know?

Anyway, enough about all that.  I knew Hillary sensed that I was pulling back a bit from her neediness and I do like her so I invited her over.  She texted me when she left and I honestly thought there was no way she’d get to my place for like an hour and a half.  Apparently though, she was horny and driving fast.  She texted me again when she got off the highway and I hadn’t even showered yet. I hurried to get ready but my phone rang while I was still in the shower and she was out front.  I dried off quickly and threw on my bathrobe and then went to let her in.  I kissed her and showed her around quickly before excusing myself to go finish cleaning up.  I got back in the shower (I needed to shave certain areas) and hurried as best I could.  I thought about getting dressed but then figured there wasn’t really any point in that so I just kept my robe on and rejoined Hillary.  I found her in the kitchen and I walked straight up to her, grabbed her and started kissing her passionately.  Things got hot pretty fast.  My cock was coming to life and straining against the terrycloth robe. 

I led her into the living room and sat her on the couch while I stood in front of her.  Hillary looked up at me expectantly and I raised an eyebrow, smiled at her and untied my robe.  It fell open slowly and soon my half-hard cock was dangling in her face.  I love that feeling and look of it being all heavy and thick and hanging low – not quite fully erect yet.  Hillary took me in her mouth and began licking all around the head.  I pushed it in deeper and soon she was sucking me pretty hard.  I know she likes it when I’m dominant with her and even somewhat rough, so I grabbed her head and forced my now hard rod into the back of her throat.  She gagged a little and backed off, pulling me out of her mouth.  She held my cock up to her cheek and coughed a little and looked up at me with a big grin on her face.  Then, she swallowed me again.  Every time the tip tickled the back of her throat, she’d gag a bit and her eyes would water but she kept at it.  Good girl!

I felt it was time for her to lose some of her clothes so I helped her strip down to a lovely bright purple bra and panty set that looked really good against her olive-toned skin.  I remained standing over her and had her return to the deep, sloppy blowjob that she’d started earlier.  She looked so fucking sexy sitting on my couch in her lacy purple undies with my hard, throbbing cock in her mouth.  I had fun grabbing the back of her head and forcing her to go down deeper on my dick.  Then, when she’d start to gag, I’d pull out and stroke it while she licked my balls.  

After a while, I decided it was time to take this party to the bedroom so I led Hillary by the hand and laid her down on the bed.  Her pretty lingerie was soon scattered on the floor and I was between her legs kissing and licking her inner thighs.  I soon made my way to her wet little honey pot and began lapping at her clit like a thirsty dog.  She really likes the way I eat her and Hillary was moaning softly and squirming above me.  I slipped a finger inside – it slid in easily since she was so wet.  I moved it in and out slowly as I ate her out, pointing it upward toward her belly to stimulate her special spot.  I crooked my finger slightly and really focused on her g-spot while I licked her clit rapidly now.  Hillary was getting wetter and wetter and I loved the squishy sound my finger made as it moved inside her.  Her moans got louder and her breathing heavier and then she came really, really hard.  I licked her clit a little longer until she couldn’t take it any more.  As I think I’ve mentioned, I’ve been fascinated with the g-spot thing lately and so I asked Hillary if I’d found hers.  I don’t even think she opened her eyes as she answered me, breathlessly and simply said, “Oh yeah, definitely”.  As I stood up, I was amazed to see a huge wet spot on my dark grey sheets.  I felt so proud at that moment!

I walked over to the other side of the bed (Hillary was laying across my bed at this point) and I grabbed her wrists and pulled her over somewhat roughly so that her head was hanging off the mattress.  I straddled her face and shoved my cock back in her mouth.  I pushed in deep so my balls were resting on her nose.  She gagged a little but continued sucking me.  I love this position – it’s so hot to me for some reason.  I think it’s because it’s a pretty dominant thing to be standing over a woman like that.  Plus, I get a nice view and I think the angle makes it possible for me to get my dick a little further in her mouth. 

I was enjoying fucking her face but, I was really ready to fuck.  I grabbed a condom, climbed on top and eased into her.  We fell into a nice rhythm and it felt really good to just sink my aching cock deep inside Hillary and feel her pussy gripping the thick shaft.  I also love that feeling of my balls resting against her outer lips when I get in really deep.  Mmm…

So, we fucked like that for a while and it was good but nothing compared to what happened when I flipped her over and took her from behind.  I had Hillary stand up and I bent her over forward so her hands were resting on the bed.  She’s quite a bit shorter than I am and so she had to stand up on her toes while I fucked her.  It was hot, but she couldn’t stay like that forever, so I put her back on the bed on all fours.  I slid my dick back inside her hot, slick cunt and fucked her hard.  I hadn’t ever asked Hillary how she felt about ass play but I decided to explore a bit and see how she reacted.  I grabbed her right ass cheek in my palm and spread out my fingers so that my thumb was right on her tight little back door.  Slowly, I worked the tip of my thumb into her ass while continued slamming into her – impaling her on my cock.  I was pounding her harder and harder and the deeper my thumb went, the louder she seemed to moan.  I guess she didn’t mind a little ass play, after all. 

It took a couple of minutes, but after a bit, my thumb was all the way in Hillary’s ass.  I began moving it in and out a little as I fucked her pussy; she was loving it.  I got a little rougher with her ass and a few minutes later, she came again.  The muscles in her upper back tightened and she let out a very satisfied moan as her orgasm washed over her.  I kept fucking her but more softly and slowly as she came.  I like sinking my cock in deep and holding it there as a woman cums so I can feel her pussy clenching and releasing.  I could tell that I just wasn’t going to be able to cum with that condom on so I went to the bathroom to dispose of it and wash my hands.  I also washed off my cock because I wanted Hillary to suck it some more and didn’t want that nasty condom taste on it. 

When I came back into the bedroom, she was lying on her back with her legs spread.  As I said, I had intended on having her finish me off orally but she just looked so sexy lying there that I straddled her and began stroking my cock.  I rubbed the head on her clit – damn, it feels SO much better without a condom.  But, I know we have to be “safe” so I didn’t try to slip inside her.  It was difficult to hold back but I did.  Anyway, I started stroking my dick faster as I held the tip against her swollen little mound.  My hand was slapping her pussy with each stroke and she seemed to be enjoying the sensation.  It was getting more and more difficult for me NOT to just shove my bare cock inside her sweet box again so I got up on my knees and continued jerking off.  As Hillary watched me, her hand moved to her clit and she began rubbing it.  We were enjoying watching each other masturbate and soon I shot a huge load of hot, white cum all over her stomach and tits.  Damn, it felt sooo good to finally cum.

We laid around a bit chatting and cuddling before she had to leave.  I thanked her for making the drive over and promised to come to her place next time her hubby was out of town on business.  I’m hoping that’s soon, of course.  All in all, my date with Hillary was a great way to start the weekend.