I was getting set for a big night with Kate, a beautiful D-Cup packing blonde smart college girl who could be sweet and also very sassy at times. We had recently had talks about how she wanted to have sex more and wanted me to be more active and initiate things more.
I was batting about .500 in recent months that we were dating in being able to keep a boner up and a condom on long enough to have some version of sex. At the time I knew deep down inside that I was still trying to convince myself I was average or mediocre.
A week prior Kate had let one slip and called my hard boner a roll of quarters as she felt it over my shorts. She was giggly and drunk and then gave me an OK symbol tug (handjob) where I would thrust up and down and then she held out the OK symbol with her pretty little hand. Usually my pathetic ass would make a load right into my shorts. She called this making “squishy pants”.
She loved doing it and laughing but tonight’s big plan was no laughing matter. It was our 1.5 year anniversary and we had big dinner plans and then a hotel room booked for a night of drinks and anticipated sex.
I was coming off a flop out the previous week but blamed it on flavored condoms and a frustrated Kate eventually accepted the excuse and I got a bonus chance for the big anniversary. With the perfect condoms picked out, KY Gel and Kate saying she was gonna be wearing pink and black VS lingerie and “looking hotter than I’ve ever seen her…” there was no possible excuse this time; I had to get it done.
After a perfect night out and fancy dinner I suddenly found myself driving home with Kate looking super hot in her black dress and me knowing what was underneath. I was already getting nervous but trying not to think about it too much. The hotel was close by but she put her hand on my thigh before we came to a stop and leaned in for a kiss. I instantly felt my boner pop up and had to do a “tuck and go” at the check in desk.
Now sweating a bit, I was at least glad I wasn’t flopping like a total useless limpy dick this time. I was thinking we’d probably settle into the room and ease into the night. Instead what happened was as soon as the key-card was swiped and we walked in the room, Kate dropped her black dress and I was left shocked stunned and helplessly sticking out with a full boner unable to speak.
“Whats wrong babe?” she said smirking as she seductively came towards me. She tackled me onto the bed and went right for the shorts. She didn’t hold back either, she went right to plowing my raging 4.5 to 5 incher right into her beautiful lips and sucking on it 5 or 6 times. She then started jerking off my insanely throbbing cock before I even had time to think!
Her D-Cup titties were spilling out her silky lingerie and her thong-ed ass was just in view as she wiggled it in the air behind her as she tugged my dick. I was never able to get any composure established and before I knew it my load shot right into the air just about hitting the ceiling and raining all over the bed and my own pecker, balls and Kate’s hand.
“Whoa that’s a lot!! But you insta-came!!” she said while laughing at me.
I laughed with her and told her how hot she looked as I began massaging her amazing body and working my way to her panties to desperately eat out her pussy as I waited for my next boner. I knew Kate expected sex still and now I had to get it up again AND get the condom on as she didn’t take any chances.
5 minutes went by and I was running out of moves, to my amazement somehow my peen felt exhausted and used up. I had shot out so much cum but never even made it in to her pussy! Now she was getting anxious and did ball grabs now and then checking to see if I was hard yet. She finally said “What’s wrong babe?” As she tried to tug my softening 4 then 3 then 2 inch dick! It just kept deflating!
She began to change her tone with me and got more intense, as she asked if I could get it up again for her. She put her titties right into my face as she straddled my cock with her hot pussy and grind-ed up and down on it. I desperately was trying to get it hard but to no avail. She stood up and stood me up and then went to her knees to try a blowjob and then she tried to shake it around but I still just flopped around all limp like a loser and then she finally snapped.
“THIS IS PATHETIC! You’re not even 30! You cant have ED, so whats wrong?”
I was stunned and mortified but had no answers to give! I begged her for another chance later and said I just needed more time to work on it but she was done and had enough. She had already been cheating on me before and knew what other cocks could do so this was clearly my last chance all along and I blew it.
Ironically we woke up together at 2 or 3 am and had a fun session when I got hard again but she didn’t let me try sex with her. It was just squishy pants at that point but only after I ate her out and she was content then she played with balls roughly and grind-ed her knee into them. She made blow a few more loads into my shorts that night like a bitch.
Kate would stick around long enough for a few more interactions and the infamous “BOOP” night and then ultimately the dumping but this was the night that really ended any chance I had of making it to 2 years or marriage.
I’m sorry Kate and I get it now! You were right about it being pathetic and I miss your thongs and big titties so much!
Damn im so horny. I used to not like tiny penis but ive begin to enjoy seeing one thinking about wat id do with it and let it do to me. Umm we could have so much fun .and id get a belly full of hot sweet boy cum
Katie pleasassseee pleeassee if you see this im ss s sooo sorrryyy im so sorry for everything and for failing your ass and pussy i really was pathetic you were right! If youll let me id love to desperately but your used panties to sniff and beg my owner Goddesss Jennnifer to let me make my pathetic loadettes in. I know that might seem odd but at this point i have nothing to lose and am pathetically just taking whatever i can get – thanks for showing me about the OK symbol and squishy pants – sorry forever and always.
HAHAHAHAHAHAHA!
Omgshhh im stilll gooooning so hard over this and now im more desperate than ever to do an OK symbollllll sesssionnmn 😭😭