This is a two-part story about an old girlfriend that led to a sexual encounter with her best friend.
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It all started when I began dating this girl named Carly. It was a Thursday night and Carly was having a girls night out with two of her friends. The girls were sitting at a table by the bar when my buddy Drew and I struck up a conversation with the three lovely ladies. I was drawn to Carly immediately because she had this cute, wholesome, Midwest look about her. She was about 5' 6" tall and I guessed she weighed about 115 lbs. It also didn't hurt that she had long blonde hair, beautiful blue eyes, milky white skin, and a pair of black pants that looked like they were painted on. For much of the night Carly did not say much as her two friends dominated the conversation. Still I was drawn to Carly as every time I looked at her I caught her staring at me. She would then smile and look away all shy-like. At around 11pm Carly excused herself and said she had to go home because she had work early in the morning. Being a gentleman, I offered to walk Carly to her car and I was happy when she accepted. We ended up chatting outside her car for about 10 minutes when I noticed Carly shivering a little. It was early spring so there was a little bit of a chill in the air. I offered to let her go, so that she could get in her car and warm up, but instead Carly invited me into the car so that we could continue talking.
We shared a little more small talk and eventually I asked Carly if she would want to go out to dinner tomorrow night. She agreed and I pulled out my phone to get her phone number. I then leaned over to give Carly a quick kiss on the cheek goodbye but was met with a full on kiss. Carly's lips were soft and sweet. They were also very moist and when she flicked out her tongue to meet mine it ever so lightly rubbed across my lips before circling my tongue. Fearing that the kiss might end, I reached my right hand up to her face and gently stroked her cheek. Carly responded aggressively by reaching her left hand across my lap and began stroking my dick through my pants. To say I was shocked would be an understatement, as my cock had not even begun to stir. But with her strokes over my pants that changed and quickly an 8 inch tent appeared in the front of my pants.
Breaking the kiss Carly said, "I'll go out to dinner with you tomorrow if you give me some dessert tonight."
Carly then reached into my pants, pulled out my dick, leaned over, and began to give me a blowjob right in the parking lot outside the bar. Here I was thinking this girl was a cute, shy girl. But as she went up and down on my dick, it quickly became clear I was wrong. Carly's blowjob was a very wet, sloppy blowjob, which I like. The added saliva from her mouth allowed her to go up and down my pole much quicker and smoother. I also liked the slurping sounds as my cock hit her in the back of the throat. Nearing my orgasm I began to grab the back of her head and slightly pull on her hair. The head of my cock began to grow and grow as Carly took me deep down her throat. I then exploded into her mouth as Carly squeezed the shaft of my cock and jacked it for all it was worth, trying to get every last drop out of it she could. As my body recovered from the orgasm, Carly sat up, licked her lips and thanked me for the dessert. Having swallowed my load, she then helped me stuff my dick back into my pants and gave it one last squeeze, causing a small amount of jizz to leak onto her finger. Not letting anything go to waste Carly cleaned the cum from her finger with a long, seductive lick from her tongue. Carly and I exchanged a little bit more small talk and set up plans to meet the next night for dinner. I even promised to return the favor after dinner, but that is a story for a different time. Playing back the earlier events from the bar in my head it hit me that I never saw Carly have one alcoholic drink. She was just a sober girl who wanted some dick.
Fast forward to about 3 months later, and Carly and I were still dating, mostly because the sex was spectacular. On this particular weekend Carly and I went to Chicago to see Carly's best friend Cheryl. Cheryl was moving apartments and Carly agreed to help her move. Being the boyfriend, that meant I was going to be helping Cheryl move too. I had seen pictures of Cheryl but that weekend was the first time I met her. Cheryl was an investment banker and lived in a 1 bedroom apartment in downtown Chicago. I guess work was going well because Cheryl was moving into a 2-bedroom apartment on the 44th floor of an upscale, luxury building about 3 blocks from her current place.
When we got to Cheryl's place on Friday afternoon Cheryl was already busy boxing up her family room. Cheryl was about 5' 5" tall, with shoulder length blonde hair, and she had a beautiful smile. I guessed her to have B-cup tits but I knew almost immediately her greatest asset was her little, tight butt. Wearing a pair of short athletic shorts, I could see the bottom of her butt cheeks when she walked into the family room after letting us in. After introductions and a little bit of small talk, Cheryl served us some wine and a few appetizers while we started packing. The girls worked on the kitchen and I got assigned Cheryl's closet to pack up her clothes.
With the girls in the other room I had no one to talk to so I made quick work of the closet. Afterwards I took it upon myself to start on her dresser and this is where things got a little interesting. The first drawer I came across was her sock drawer. I emptied most of her socks into a plastic bin and then came across a small, purple, felt bag. My hope was that this was some sort of sex bag so I was excited to see what was inside. Not wanting to get caught I casually walked over to the bedroom door just to verify the girls were still in the kitchen working. Then I walked back to the dresser and opened up the bag. The first thing to fall out into my hands was a pair of nipple clamps. Connected by a long silver chain, the end of the clamps were pink and had a long silver screw to adjust the tension on them. The next thing to fall out of the bag were four condoms. There was still some weight to the bag so I tipped it over to empty it out and out fell a string of anal beads. Growing in size from the bottom to the top, the ten pink beads rolled around in my hand as I began to imagine Cheryl using them. I quickly brought them up to my face and I breathed in what I imagined was a mixture of Cheryl's pussy and ass...and I must say it smelled good. I quickly returned the items into the bag and threw it into the bin with the socks.
Now being slightly aroused, I opened the next drawer and was happy to discover Cheryl's underwear drawer. I'm sure there were some old, nasty pairs of underwear in the drawer, but my eyes were only drawn to the sexy pairs. My first handful of underwear included a pair of red, white, black, and leopard print thongs, which I held in my hands for a few seconds before putting them in the bin. Returning my attention back to the drawer of underwear I picked up a few more pairs of panties and in doing so I uncovered a small cigar box located at the back of the drawer. Looking at the box I had a strong feeling I wasn't going to find cigars in this box. Again checking to make sure I wasn't going to get caught, I could hear the girls still laughing in the kitchen. Lifting the lid to the box I knew immediately this was Cheryl's main sex box. My fingers first ran across a smooth, solid gold vibrator.
Next was a battery powered purple and pink rabbit vibrator, with ass stimulator. Rounding out the contents of the box were a small pocket rocket vibrator, approximately 12 more condoms, and 2 flesh colored dildos of different sizes. I quickly put the box and it contents into the bin with the rest of the clothes and continued emptying the dresser. Eventually I came across Cheryl's bras as well. Like with her panties I was drawn to the sexy lace bras. I noticed most of them were size 32B but there were a few 32C as well, making me think she was on the larger size of the B-cup. As I was emptying the last drawer of t-shirts and tank tops both girls walked into the room to see how I was doing. I told the girls I had emptied out the closet and dresser and made sure to look at Cheryl to see her reaction.
"Did you get everything out of the dresser and into the bin?" she asked.
"I sure did, everything," I replied.
