Last weekend I traveled to Chicago to see my friend Blake who recently moved back home to Chicago. I arrived there Friday, along with some other friends and we went out to the bars that night. We bar hopped for a few hours and gained and lost people in our group by the time we arrived at this small bar that was a nice change of pace from the noisy and crowded clubs we were just at. I noticed two women sitting at the bar close by us. One was a brunette (Heidi) with a slightly foreign look about her; the other was a cute blonde with rather large boobs (Kate). I walked up to the brunette and introduced myself and we started talking. It turns out she moved to the US from the same country that one of my friends at the bar was also born in. I introduced the two of them and we all started talking. Heidi and my friend talked about growing up in same country, where they were born, their relatives back there, and so on. Thinking that my friend and Heidi were hitting it off I went back to talking with my other friends at the bar that night. Some time later Heidi came over to me and said that her and Kelly were going to another bar. I took that as an invitation and joined her. We were followed by one of Blake’s acquaintances who had his eyes set on Kate. Heidi, Kate, myself, and this other kid went to a bar where Heidi and I proceeded to make out for about half an hour. It was sort of a drunken blur now that I try to remember it. My next clear memory is being outside of the bar with Heidi. She said that she was gonna call it a night. I asked if I could see her again. Heidi asked me how old I was. I said I was 26. Heidi said that was too young for her since she is 32, however she still gave me her number. On Saturday I texted Heidi and we agreed to meet up at a rooftop bar for drinks. As the night progressed Blake and Kate seemed to be hitting it off, while Heidi and I were getting along okay but I didn’t think anything was going to happen. At one bar Heidi and I found a quiet place to sit and talk for a bit. She told me that there was too big an age gap between us (6 years) and she was looking for something serious. This made sense and I said it was okay, but we should try to see that Blake and Kate have a good night. Pretty soon it was near 4 am and we were calling an Uber for Heidi and Kate to take back to their hotel room (they were also visiting Chicago). I thought this was where we were going to say goodbye but to my surprise Blake was in the cab, so Heidi gave me the go ahead to jump in too. We arrived at their hotel and went into their room for some snacks and a nightcap. After we undressed a bit and turned off the lights Blake and Kate made out for a bit in Kate’s bed and Heidi and I started making out in Heidi’s bed. It appeared that Blake and Kate fell asleep shortly after the lights went out but we weren’t entirely sure. Heidi and I were way too turned on to care.
We started shedding more clothing: Heidi lost her bra and shirt, and I stripped down to nothing. Once her bra came off I quickly zeroed in on Heidi’s succulent C cup breasts. I grabbed them, sucked, pinched, and bit them to her delight. Our bodies were intertwined as we groped at each other and kissed passionately. It was a major turn on to be naked in bed fondling a woman 6 years older than me. Until that night I had only been with one woman older than me and that was a girl only about 6 or 7 months older than me. Heidi ended up giving me a handjob under the sheets in bed only a few feet away from her friend and mine, who we (correctly) assumed were asleep. Being a hotel room, I didn’t care so much and freely came on the sheets (gross to think about, I know). And we passed out around 5 or 6 am exhausted from the drinking and shared pleasures of that night. Heidi and I woke up a few hours later and continued to fool around. It was brighter in the room, but with the shades drawn close it was still somewhat dim. My hand found its way in between Heidi’s legs. I started rubbing her pussy from the outside of her panties. I could feel her dripping down her legs and soaking through her underwear. We were facing away from our sleeping friends, but if they were to awake they would still catch a pretty good glimpse of what was going on. Heidi tried hard to keep her little moans and sighs of pleasure muffled into the pillow as I continued rubbing and playing with her pussy. I’m not sure if she came or not, but she whispered in my ear that I should get off again before our friends woke up. We shifted our bodies so that her back was facing our friends as she pulled my cock out from my boxers and began stroking me again. This time I could see her hand grip around me and smoothly stroke up and down. It was such a turn on receiving a handjob from an older woman in the same room as two other people that I was trying hard not to make too much noise because I was so excited. She looked down at my cock as she stroked it and watched me cum onto my stomach. After I came she kept her hand on my crotch and looked up with a seductive grin and we began to kiss lightly until we both fell back asleep. Exhausted from the night before we all slept in til midday. Nothing else really happened after that. We grabbed some food together and said goodbye as they left to go back home. It was a nice part of my trip and the first time I hooked up with an older woman and the first time I received a handjob with other people in the room. Thinking back, I wonder if her friend Kate, who was sleeping closest to us and facing our bed, saw anything that was going on?