Windy City Weekend

Post divorce and after finding a nice apartment on my own I had fun on the internet exploring chat groups and engaging with new people in various discussions. Inevitably the conversations almost always turned sexual and it was fun and exciting to allow myself the freedom to participate in some of these sessions. It was new for me and to chat in suggestive and flirty teasing ways with a range of guys I discovered it allowed me to be creative and could be really arousing, too. Sometimes, not often, but on occasion it happened that there was a real connection. It wasn’t too hard to tell if the guys were masturbating over the chat and if the mood or need was there and present it was easy to let my fingers do more than the just the typing.  Probably the wildest session was a multi guy event where three different guys were telling me how they’d take me and what they’d do to me sexually and it ended up becoming a mutual masturbation session wherein all four of us came in an imaginative group gang bang session. It was one of the hottest cyber-type sex sessions I’d ever had.

There was one guy in particular with whom I’d built a long distance friend ship over a number of months. He was kind, sincere and seemed both genuinely interested in me and had a great sense of humour.  We were able to chat and share in unexpected ways. Atypical of me and on an unexpected whim he suggested we meet and I couldn’t get the offer out of my mind and over a period of weeks I found myself planning a road trip to meet him in a restaurant for dinner. He and I booked accommodations at a nice hotel and by this point we’d shared and exchanged personal details and pics and both of us felt connected and attracted to each other. So on a long weekend I packed for a road trip and drove the long distance to The Windy City.  With time to spare I checked into the hotel, refreshed myself after my travels and the stress of navigating in an unfamiliar city in traffic.  A shower and some pampering relieved the stress and changing into a fresh white blouse and dark form fitting pants I took my time putting on make-up then made my way to the dining room for our first in-person meet. We recognized each other immediately in the Lobby and nervously smiled and touched hands and he being a gentleman kissed me on the cheek. We made our way to our table and ordered cocktails.  He was better looking and bigger than his photo had suggested and something in me sensed this was going to be great.  Dinner and dessert were highlights and the conversation was engaging and fun and the evening slipped away with a few glasses of wine.  We agreed to continue our conversation up in his suite and made our way to the elevator.  In the ascending car we held each other for the first time and shared a first tenuous kiss that evolved into a passionate one.  He opened the door to the suite and closed the door behind us.  The view through the patio glass of the night skyline of the city lights was spectacular and as I stood there gazing he wrapped his arms around me from behind and nuzzled my neck pressing his body in behind me. I could feel his member semi erect standing up in the front of his pants pressing against my buttocks  and his hands moved to cup my breasts through my blouse then rose to my neckline and began unbuttoning it moving down. I reached a hand behind and caressed him though the front  of his dress pants and what I felt was a lot bigger than I had imagined. With my blouse unbuttoned and gently tugged from my waist band his hands returned to my breasts and ran over top of my bra. I could feel my nipples tighten and begin to stand erect and he could, too. He moved his hands up to slide my shoulder straps off and his fingers undid the back clasp.  My bra slipped off and my boobs toppled forwards out of the cups and were exposed to his touch and sight. I turned around to press them against his chest and said, “This isn’t fair” and began unbuttoning and removing his shirt until his muscular chest was bare against my skin.  I could feel myself flush and we kissed deeply exchanging tongue and he moved me backwards towards the king bed laying me down and moving his hands down my waist to undo and unzip my slacks and began to pull them down over my hips.  Topless and in my panties I fumbled to release his pants and pulled both his pants and his briefs down and the biggest most beautiful chocolate coloured  cock I had ever laid eyes on sprung out and up.  I was both amazed and afraid at the same time as it seemed to be the size of a paper towel roll in length but thicker and touching its smooth head I could feel the prelube spilling out and spread it around his tip.  “Are you sure you want to do this?” he asked and I said,”Yes but I’m not sure I can manage all that. Go easy on me.” He let his pants and underwear fall to the floor and stepped out of them and gently pulled my panties off over my hips, down my thighs and calves and over my feet.  He lifted my leg and held it by my calf and sucked my big toe into his mouth. It felt erotic having my foot being held and massaged while he sucked on my toes.  My leg was up in the air with my trimmed pussy on pretty much full display for his viewing. He positioned me so my buttocks were at the edge of the bed, spread my legs and moved between them. I could feel him gently placed the swollen head of his big cock between my pussy lips and he pressed just enough that his glistening head probed inside.  I was already wet and when he inserted about a third of it he pulled out almost to the point of exit then slid forwards into me again an inch or two further.  There was no pain as I’d expected just a sense of fullness and on the next slow insertion he gave me more and I reached up to grab two pillows and prop them under my shoulders and head so I was raised and tilted up. I wanted to see this happening.  My full boobs were on display with their pinkish nipples standing erect and almost demanding attention and his hands began to caress and gently squeeze them as I looked down to watch his cock slide further into me and the sight was incredible. He had at least three more inches of shaft to dip and in two more slow thrusts the whole length of it was deep inside me and I was wanting it.  He began to slowly pump it in me and my pussy was slippery wet with both our combined lube - it looked as if I was being tunnelled with a table leg and I told him he could fuck me harder.   He spread my legs more and moved up between my thighs and began swinging his pelvis plunging his cock all the way into me and pulling it out to thrust forwards again and I tilted my hips up  to receive him and moved in time with his forwards thrusts. Never had I been this full even though my favourite sex toy was a pretty good size but this felt incredible and my breathing was getting faster. He removed a hand off my tits and turned it palm forwards to rub my mound with his fingers as he began fucking me in earnest.  More than caught up in the building heat of the moment and the intense sensation of being plowed by this huge cock and his rubbing of my clit I threw caution to the wind forgetting I really should have asked him to use a condom but instead I pulled him atop my chest and breasts and shimmied with him up in the bed. He began to plunge inside me like a piston and slammed into me his cock absolutely pounding into my gaping cunt. I knew I wasn’t far from a fast rising orgasm as I gasped and moaned and clutched his hips and buttocks to pull him hard into me and all our built up excitement and sexual tension crescendoed.   He worked me so good I knew I was going to cum and I bucked and arched and exploded in ecstasy.  “Oh, oh, oh!” I called out, “Fuck me hard! Pound that pussy” and he obliged slamming full bore into me with that huge cock. I felt it swell and throb and a first jet of spunk shot deep inside me and three or four more spurts. I wasn’t just full of cock but now was full of his cum, too.  He collapsed on top of me and when both of us had caught our breath I felt him begin to withdraw and retract and I looked down between my legs to see what looked like like a big salami pulling out of my pussy and globs of cum spilled out as he did. He had to have had a huge load and he’d deposited the bulk of it up inside me.  I could feel some of it drip out of me and run down my asshole between my butt cheeks and onto the sheets. At least I wasn’t going to sleep in the wet spot.   It was my first BBC experience but it wasn’t my last for the weekend.