It was a the weekend, and being it was the day to go grocery shop, i got dressed and headed out. I usually tried to get through grocery shopping as quickly as possible, but this visit would be one to remember.
It started out as just a regular weekend and being this was the day to go grocery shopping, I got dressed and headed out. I usually tried to get through it as quickly as possible, but not this time.
As I made my way around the store, everything was going the way it always did, but then I happen to see a nice looking, young lady doing her grocery shopping a little ways in front of me.
Wanting to get a better look, I tried to move up, hoping to pass her. From behind, she was kind of petite, had blonde hair that was cut short, kind of bobbed and from a distance, even though the blue medium length wool coat she was wearing covered her, and the loose fitting black leggings hid her frame, I could see she had a thin build.
Immediately, I made my way to the next aisle, deliberately trying to go in a way so we would pass each other. As I turned down the next aisle, there she was and as I watched her grab something off the shelf, I smiled.
Continuing down the aisle trying to act as nonchalant as possible as we approached each other, hoping we’d make eye contact, I smiled and deliberately steered my cart toward her. Looking up briefly and smiling, she shyly moved to one side. As we eventually passing each other, she again shyly looked at me and seeing her smile, I said, “Sorry.”
It was obvious she didn’t want to make eye contact, and I wasn’t sure if she was just shy or maybe a little bashful, or maybe she too just wanted to get through the store, hoping not to run into anyone.
In any case, after seeing her up close, I was attracted to her and wanted to see if I could get her to talk with me. She really was very attractive in a plain sort of way and even though the blue wool coat conveniently hid her body, her shyness was alluring.
Any way, even though I was nervous, in the next aisle I decide to make a move and try to talk to her. Looking up briefly and giving me a smile as I approached her, I took a deep breath and simply said, “Hi.”
I think it surprised her but as she looked up at me with a sheepish grin she too replied, “Hi.”
I wanted to try to keep her talking and so as we passed each other I turned and said, “I know this is kind of cliché but I think I know you.”
Stopping, she turned, and seeing her smile again, I search for what to say. She seemed to like the fact that I said something because I could see it made her blush a little. As I moved back toward her in the aisle, she asked, “What’s your name?”
She really had a great smile and pretty blue eyes, and in a sexy way her short straight thin blonde hair showed off her high forehead. As we stood there exchanging pleasantries, I glanced down, looking at her hands to see if she was wearing a wedding ring. Not seeing one, I immediately looked up smiling, and extending my hand, I introduced myself as we shook hands. She told me her name was Penelope, and as I smiled, I told her I never knew someone named Penelope. She smiled and said, “People just call me Penny.”
Smiling, I shook her hand and said, “It’s nice to meet you Penny.”
As she looked at me, I immediately wanted to keep her attention, wanting to see if she might want to go out. Continuing to talk, I found out that she had just moved in to the new condos across from the grocery store. She seemed very excited to tell me about it as she explained that she had to find a place to live.
Listening intently, she inadvertently let it slip out that she was recently divorced and that she had two kids. Not knowing what to say I paused and then said, “That’s too bad,” but she shrugged it off by telling me, “It’s okay.”
The condos she was referring to were brand new and when I asked if they were nice, she immediately said, “Yea, they’re really nice.”
Looking at each other there was a brief pause, but then she asked, “Do you want to come over some time to see them?”
Smiling and without hesitation I said, “Yea, that would be nice.”
I couldn’t believe it but it was my chance and after exchanging phone numbers we made plans for me to come by. She told me that she’d text me later and as we parted ways, I was excited at the possibility of being with her.
At home, I waited impatiently for her to text me later that day and when she finally did, I could hardly contain myself and jumped at the chance. Texting her back, I asked for her address. It seemed to take an eternity, but when she finally sent it to me, I immediately said, “I’ll be over in a little.”
I was excited to spend time with her and nervous too as I pulled into the parking lot. Parking out front of her building, I got out of the car, and as I looked up at where I thought her apartment was, I smiled and quickly headed toward the door. She had to buzz me in and after saying come on up, she buzzed the door. Taking a deep breath and heading up to her floor, I was so excited and when I knocked on the door, I again took a deep breath and waited patiently.
As she opened the door, I nervously stepped back slightly and then tried to put a big smile on my face. Seeing her smiling too as our eyes met, I excited said, “Hi.”
She was wearing a white sleeveless top, and the same black leggings from earlier, and seeing her without the heavy wool coat, she really was very pretty. She had a great shape and like I thought, she had a thin frame and small boobs. She had done her hair a little, and put on some makeup, and the raspberry lipstick really brought out her face.
Inviting me in, I immediately said, “Wow, this is really nice.”
Penny quickly responded, Thanks, I like it a lot too.”
It still smelled new and as I walked further into her condo, she directed me toward the living area, which was right off the entry. As Penny now closed the door and as I turned to look at her, she motioned and told me, “Go ahead and have a seat.”
We talked for a little bit and then she suddenly said, “Oh yea, did you want me to show you around a little?”
Repositioning myself and sitting up, I excitedly said, “Sure.”
Penny quickly stood up and as I stood up too, she jokingly said, “Well this is the living room,” as she smiled and waved her hand.
I again said, “This is really nice.”
It was an open floor plan and as she moved over to the kitchen area, she smiled and presented it with another wave. Penny giggled and as she took my hand, she looked at me and then led me down a short hallway.
I was a little nervous but as she pointed out a small bedroom and we stepped inside, she explained that this was going to be her two kids’ room. It was decorated nicely, and when I asked where they were, she explained, “They’re staying with their father until I got a place.”
The bedroom was nicely furnished for her kids, set up with two single beds a dresser and a chair, and as we left the room and proceeded down the hall, there was a small bathroom across from the kids’ bedroom.
As Penny led me a little further down the short hallway, and we went into what was obviously her bedroom at the end of the hall, she seemed excited to show me. As I moved around the room a little, I could see it was a master bedroom with a queen size bed, and matching nightstands and a dresser.
She seemed to become a little nervous and after showing me the master bathroom toward the back, she immediately tried to usher us out. Heading back into the hall, I smiled, hoping we’d be visiting her bedroom again, but didn’t want to press my luck.
We ended up back in the living room and as we sat on the couch, we talked and joked about a lot of stuff, but as the conversation lulled, I asked if she wanted to go have a drink and maybe get something to eat.
There was a nice little restaurant in a strip mall caddy corner from the grocery store, just down the street from her complex and when I suggested it she lit up saying, “Oh yea, I know where that is.”
Smiling I said, “Okay, you wanta go?”
Nodding, we both stood up and as we left and headed toward the parking lot, she said, “Maybe we should drive ourselves and meet over there.”
I was a little confused at first, but then realized that she was probably a little hesitant being she was recently out of a relationship. Agreeing, we left in separate cars and I made sure to follow her so we could at least park near each other.
At the restaurant, we ordered a couple appetizers and again joked around as we had a few drinks. It was nice, she was very easy going and the more we drank, the little more personable she seemed to get.
Any way, after a little while we ended up going back over to her place and as we went up the walk toward the door, she took my hand. It surprised me but as we got to the front door, she turned, gave me a kiss on the cheek, and said, “I had a nice time.”
“Oh no,” I thought, but then I guess seeing my confusion she asked if I wanted to come up for a little bit.
Smiling, I of course said, “Sure,” which made her smile too.
Inside, she asked if I wanted something to drink and when I asked what she had, she suggested we could have the same thing we had at the restaurant.
Sitting on the couch, waiting for her to come back out from the kitchen, all I could think about was, “How can I get her in bed.”
I know that’s kind of bad, and seeing we were both feeling no pain, I felt it might actually happen. Smiling, Penny handed me a drink, and then sitting down she asked if I wanted to watch some TV. I definitely needed something to preoccupy my thought so not to betray how I was feeling.
After a little while, I casually moved closer to her and as we looked at each other, she said, “What?”
I had a big smile and not saying anything right away, I shook my head and reaching over, she looked down as my hand touched her thigh. When she eventually looked up again, she smiled, and after putting my drink down on the coffee table and taking hers and doing the same, I leaned toward her and gave her a kiss.
It was nice and after looking at each other smiling for a moment, we kissed again, letting our tongues mingle. As we passionately kissed, I reached my one hand up until it cupped her left boob. Moving my hand up until I was feeling on her boob, Penny let her hand drop between my legs. Spreading my legs slightly, she moved her hand up, until she was feeling on my crotch.
When we happened to stop kissing and looked at each other, Penny smiled and then stood up. Not sure what she was doing, I looked at her inquisitively, and then smiling she motioned for me to follow her. Smiling myself, I stood up and as she took my hand, she led us back toward her bedroom.
As we went through the door, she turned and then leaning toward me, she gave me a kiss. I knew we’d be back in her bedroom and as we held each other and kissed, I again let my hand slide up to her chest. She really had small boobs and after a little while, I let my hands move until they were both on her firm little butt.
Giving her ass a gentle squeeze as we continued to kiss, she too put her hands on my ass. This made me smile to myself and then feeling a little feisty, I put both my hands down the back of her leggings. As my hands found their way further into her legging, the waist band happened to flip down a little as my hand moved past the thin band on her panties.
I could feel Penny smiling as we kissed and then she moved her hands to the front of my pants, fumbling to get them undone. Realizing what she was doing, I leaning back and took my hands out of her leggings. Smiling as she got them unbuttoned, I tried to give her better access, and immediately tried to lift her shirt over her head.
Seeing her hard little nipples, I smiled and quickly reached up feeling on her soft, flaccid little tits through her bra. Penny eventually got my pants unzipped and inched them down until they dropped to the floor. I could see her smiling and as she reached down to feel on my cock through my boxers, I rolled down her leggings a little.
After getting our clothes off, Penny climbed on the bed and as she watched me take off my shirt and my boxers, she backed up on the bed. She was seductively posing, showing off her body with one leg bent and the other spread slightly. I couldn’t believe it, but as she sheepishly looked at me, she spread her legs. She had great legs and as she looked down, I couldn’t help but look down too.
Penny had one hand on her thigh and seeing her shaved little pussy, I moved closer to the bed. Penny leaned toward me and taking hold of my hard cock, she started stroking it. It felt good and as she looked up at me standing there she asked, “Do you like that?”
She was obviously a little drunk and giving her a nod I simply said, “Yea,” as I moved right against the bed.
As se continued to jerk my cock, I was instantly hard and when she happened to lean forward a little more, I thought, “Maybe she was going to suck it.”
Instead she looked up at me and smiling, she let go, and moving to the middle of the bed, laying on her side, facing away from me, I watched as she reached back spreading her ass, and eventually started fingering her pussy from behind. I wanted to be in her and as Penny now leaned forward, spreading her legs a little more, I casually climbed on the bed behind her.
As I inched closer to the bed, Penny looked back smiling. She then reaching back, taking hold of my cock, and pulling me closer, I felt she wanted me in her. Penny awkwardly tried to rub and stroke my cock as I positioned myself behind her, but then stopped and went back to finger herself.
It was really turning me on to watch her but then she suddenly leaned forward and took something out of the nightstand. It was a tube of lube and as I watched her squeeze some out on her hand, she again reached back again fingering herself. Continuing to jerk myself wanting to fuck her as I watched, she pushed her ass back toward me.
Spreading her legs and reaching back, spreading her pussy lips she again took hold of my cock smearing some of the KY on it. Moving closer, she guided me to put it in her and as I took hold of my cock, I slowly pushed into her.
She was really tight even though she had two kids, and when I said, “You’re really tight,” she glanced back and smiling said, ”Like a virgin,” with a slight giggle.
Penny definitely wasn’t a virgin but agreeing I said, “Yea,” as I grabbed her waist and slowly started moving my cock in and out of her, fucking her.
She really was tight and when she happened to reach back and spread her ass, I couldn’t help but looked down. Seeing her tight little pucker butthole made me spread her ass cheek too, I thought about wanting to fuck her ass. Penny then spread her pussy, and as I went back to fucking her, I reached forward and felt on her little boobs.
I really wanted to cum in her; I didn’t want her to stop me, but when she suddenly rolled to her side and moved to lay on her back, I smiled and moved us up on the bed. Penny brought her knees up, and as she spread her legs, I moved between them.
She really was sexy and when our eyes met and I saw her smile, I again reached up, feeling on her boobs. Leaning down to kiss her, I reached down and tried to guide my cock in her again. As it went in, she pulled away slightly, gasped, and then wrapped her arms round my neck, holding on as I pushed into her deeper.
It felt so good and as I started moving my cock in and out of her, fucking her again, it didn’t take long. I was close to cumming, and I think Penny could sense it too, because she suddenly stopped me and said, “Don’t cum in me.”
Stopping, I looked at her and smiling, I nodded, and then after giving her a subtle kiss, I returned to fucking her. Immediately out of breath as I hunched over her with my hands under her shoulder, I tried to move faster with deliberate strokes.
Penny was now holding my sides, and feeling her trying to help, I really wanted to cum in her, but knew I had to pullout.
I was going to cum and after a couple more deliberate thrusts, I pulled out and knelt in front of her jerking off. Penny immediately leaned up on her elbows to watch and as she rubbed her fingers along her sides, I concentrated on wanting to cum.
Leaning forward as cum shot out, she pulled away slightly. Eventually after a couple good shots of cum, Penny reached out and took ahold of my cock. I could see she was smiling as she continued to stroke it.
Cum only dribbled out now, but her stomach was covered and there was a little that had dribbled down toward her pussy. It really felt good to have cum, and seeing her smiling, I took my cock from her. Looking at her as I squeezed the last few drops out, I moved to put my cock back in her.
Penny hastily said, “No, don’t!”
Smiling, Penny pushed me away and as I tried to lay next to her, she rolled off the bed, and headed into the bathroom. It wasn’t long before she returned again and rolling to my side, I could see she had a big smile on her face.
Penny quickly climbed back into bed with me and as we lay together, we kissed. Leaning toward her, I moved my hands to gently felt on her tits.
It was way late and as we lay together, cuddling we eventually both nodded off, falling asleep. Later when I happened to wake up, I realized it was actually almost morning.
Feeling I should probably get going, I stirred a little, which woke her up. Penny smiled and leaning toward me, she gave me a kiss and said, “Good morning.”
She had a big smile and as we laid there holding each other, I could see that the sun had started to creep in through the window. After a few minutes, Penny explained that her kids where coming over, which suggested I should probably get going.
After getting dressed, she walked me to the door wrapped in the sheet, and after a kiss, I left.
We didn’t talk to each other for a few days, and when we finally did, it was definitely superficial. Penny explained that her kids were spending a lot of time with her now, which told me she was going to be busy.
I hoped we might be able to meet up, but it never happened. To this day we, every time I go to the grocery store, I looked for her, hoping to run into her again.