I couldn’t get her out of my mind; I was obsessed with her, and even created a fake Facebook account so I could at least see more recent pictures, I also saw that she had gotten married. However, I came across a Linked profile and seeing she was secure in her present job, I reached out to acknowledge her recent promotion.
It had been a long time since Kaitlyn and I got together, and even though I had continually thought about her, how could I not, I never expected to see her again. Last time we spent time together, she was so much more younger than me, and the thought of being with her again, especially after the first couple of times, well was always on my mind. I desperately wanted to keep in touch, but it was obvious she was trying to move on because she had blocked me from her social media, and she wasn’t responding to my emails, even the ones that simply said, “Happy Birthday.”
I was let say, obsessed with her, and wanting to at least see her on social media, I created a false Facebook account, so I could at least see recent pictures, being I hadn’t seen her or talked to her in 2 or 3 years. I knew she was in a relationship now with a guy and yea, there were photos of her when she was younger, but there were also pictures of the two of them that obviously showed she had apparently gotten married to him.
It was nice to at least see photos of her, because she still looked good, and they did make me smile, and being able to see her, even though it was only in pictures, brought back old memories of being with her. Any ways, I continued to discreetly look at her postings, and I did think about trying to contact her, but feeling it might turn her off, I kept my distance.
I was torn, I wanted to contact her, but being she was married now, I knew it would probably turn her off, and as the years passed, I came to realize, “It just wasn’t meant to be.”
Of course, whenever she would happen to come to mind, I would continue to look at her postings and fantasize about being with her again. However, as a few more years passed, I could see from the more recent photos of her that she had gotten, well let’s say heavier. No she wasn’t fat, I didn’t want to think that, but yea, she had put on some weight.
Way back when I first saw her at Starbucks, Kaitlyn was very petite, probably only about 100 pounds, but now she looked to be, I don’t wanta say it, maybe about 50 pounds heavier. She still seem very happy, smiling, which made me smile too, continuing to think, “I really wanta be with her.”
I did try to put our time together behind me, but I couldn’t help look at her postings and seeing her with more than a few extra pounds made me think, “Maybe she’s pregnant,” but really, she didn’t look like she was, and there were never pictures of a baby.
Kaitlyn still had that infectious smile, and even though she was married to this guy and they looked happy in the photos, my attraction to her was still there. I always wanted to see more pictures of her, and even though she was on Facebook, her newer postings were locked.
Wanting to see more of her, I searched online, but never found her on Snapchat or Instagram or even TikTok. Eventually, I did an online people search, and even paid money to find out where she now live. I know it’s obsessive, I already told you I was, but I wanted to see where she lived, hoping maybe I’d run in to her.
Eventually, I just happen to find her on LinkedIn, and even found more pictures of her with her new last name and being that she now seemed to be more secure and that she was maybe 6 years older, I decided to take a chance and contact her through her LinkedIn profile.
I was still worried how she’d take hearing from me, but after creating a simple message to recognize her work experience, I hit send. It made me nervous and never expected a response, because she had never responded to my emails or messages before, but I checked often.
After a while, I came to realize she wasn’t going to respond but then suddenly, out of the blue, there it was. It too was a simple system reply saying, Thanks.”
I was shocked, but it was nice to finally have some communication with her and when she too messaged me about my work experience, I smiled thinking, “Maybe.”
She was a few years older now, and even though we were a tiny bit closer in age, she was still, well a lot younger, and when I boldly messaged her asking, How’s everything going,” she didn’t respond back.
Immediately, I thought, “She’s just being friendly, responding to my message,” but when I finally got a message from her tell me, “Everything’s good,” I became nervous thinking, “Should I message her back.”
However, before I could even finish thinking about what to do, I got another message from Kaitlyn asking, “How have you been?”
It was nice, and feeling she was open to talking, I tried to keep our messaging going. Again, it was nice to finally be talking with her, and as we continued to communicate back and forth, I decided to take a chance and ask if she wanted to meet up. I was nervous, I had wanted this chance and after asking, she again didn’t message me back right away.
I became scared, thinking I overstepped, but after a little bit, I got a message back saying, “What are you thinking.”
Immediately, I searched for what to do or where we could meet up, and knowing she lived farther away now, I looked at restaurants closer to where she lived.
I wanted to see her, and even though I hoped I might have a chance to be with her, I at least wanted us to be friends again.
Thinking for a moment, I suggested, “How about, Chili’s or Ruby Tuesdays or Bennigan’s,” something like that, and when she mentioned, “Let’s meet at the Chili’s,” I anxiously agreed.
It was convenient, close to where I lived and close to her too. I of course was more than excited to see her, and after deciding to meet that Friday afternoon, I thought, “Think she’ll bring her husband?”
I really didn’t want to think that, but either way, I knew I had to go into it with an open mind, and that afternoon, I made sure to clean up best I could, and continued to tell myself, “Just stay cool.”
I had told Kaitlyn, I’d get there early, so I could get us a booth, and the minute I got to the restaurant, I made sure to ask for one that was more secluded, more toward the back.
Sitting down, I couldn’t help smile as I anxiously waited. I was excited to see her, and watched anxiously for her to come in the front door, and then suddenly, “Oh my god, there she is,” I thought.
Scooting back in my seat, I waved to her, and when she saw me she smiled and headed my way. Getting up out of the booth to meet her, and seeing she hadn’t brought her husband was a relief.
Walking toward me, she was wearing a red plaid flannel shirt that was untucked and unbuttoned to help, I think hide the fact that she was a little heavy, and as I continued to look at her, I could see that she was wearing an off white spaghetti strap tank top under her flannel shirt that, more than accentuated her cleavage now that she had fuller boobs being she was heavier.
Smiling, I couldn’t help but look down at her legs, and seeing she was wearing some black leggings and some flats, I immediately looked back up and again figured she was wearing leggings to help hide her shape.
Continuing to smile I said, “Hi,” and after shaking hands, I boldly stepped toward her, giving her a hug.
It was only for a moment, but the smell of her perfume on her neck was exhilarating, and after an kind of awkward moment, we eventually both sat down across from each other, and as we smiled, searching for what to say, I excitedly said, “You look great.”
It did make her smile, and after adjusting her shirt to self consciously cover her boobs, she told me the same. We both seemed to be nervously searching for what else to say. I was desperate, I wanted to keep this going, and when our waitress came to our table, I blurted out, “Do you want to order drinks.”
Kaitlyn smiled excitedly and after a nod she said, “Sure.”
“Great,” I thought, and feeling she’s okay with seeing me, I smiled and asked, “How ‘bout we get some appetizers too?”
Smiling, she agreed and after placing our order, we again made small talk, trying to stay easygoing as we caught up.
It was nice, but I was nervous, and I think she was too, but we both seemed to calm down after a little bit, but when I happened to ask about her husband, she asked, “How did you know I was married.”
I had tipped my hand, and had to tell her I was trying to follow her on Facebook. Hearing this, she smiled, but then after a brief pause she looked at me and said, “Well you haven’t seen.”
Confused, I smiled and when she said, “We got divorced,” it surprised me.
I tried to act concerned saying, “That’s too bad,” and then asked, “What happened?”
She was unsure how to respond at first, I think, but eventually said, “It just wasn’t working out.”
Looking at each other, I reached across the table and as she brought her hands up to mine, I took her hands, and giving them a gentle squeeze saying, “I’m sorry.”
It did make her smile, but she looked concerned, maybe concerned what I would think, and after letting go of her hands, I tried to console her by asking, “Are you okay?”
She looked down briefly but then looking up she smiled and said, “Yea, we haven’t seen each other for a while.”
I wanted to change the subject and I think she did too, because she looked up and said, “It’s really nice to see you.”
Smiling at each other, we both took a big gulp off our drinks, and as we continued to talk, I tried to keep it easy going, but I wanted her to know the same, and smiling I casually as possible said, “I’ve thought about you a lot.”
Again, it made Kaitlyn nervously smile, and being unsure, she seemed to ignore what I said, instead picked at our appetizers as we both pounded down our drinks. There was an awkward paused, and feeling a need to change the subject, I asked, “How’s your job.”
Smiling, she looked up and then proceeded to tell me all about it. It made me smile too, and as I tried to act interested, it was a genuine relief to see we were enjoying each other’s company.
Eventually, we did order another drink, and being we were both probably feeling no pain, and seeing she was more loose, I felt she was actually liking just hanging out for a while longer.
However, when there was suddenly a lull in our conversation, and seeing her look to leave, I stepped up and boldly asked, “Do you wanta come over to my house? “
I wanted to keep thinks going, I didn’t want to let her go, and yea, it was bold, I know, and I could see her hesitate, but when I casually said, “We can go watch something on TV,” she smiled and innocently replied, “Okay.”
I was excited, and not wanting to appear too overly anxious, I simply smiled saying, “Great!”
Immediately, I flagged down our waitress, and after paying the bill, we both finished our drinks and then got up to leave. As we left the restaurant and got out to the parking lot I asked, “Do you wanta follow me?”
Smiling, Kaitlyn nodded and asked, “Do you still live in the same house?”
I was surprised, “Did she remember?”
It did make me smile and simply say, “Yes.”
Leaving the restaurant parking lot, we headed off, but seeing that the sun was already going down, I decided to hurry. It wasn’t late, but being it was already past time change, it was starting to get dark earlier and earlier.
Anyway, as we left, I could see Kaitlyn was trying to follow me closely. Eventually, I turned into my neighborhood and then pulling into the driveway and parking in the garage, Kaitlyn parked out front.
Quickly, I got out and when I came around my car, she was already walking toward me. Smiling, I ushered us in through the garage, and as we went inside, I asked, Do you want anything to drink?”
When she didn’t answer right away, I turned and as I faced her, she finally asked, “What do you have.”
Smiling, I suggested, “How about a beer,” as I went to the refrigerator.
Opening the door, I grabbed two out, and after opening one, I handed it to her, and immediately moved us toward the living room.
Slipping off my shoes, she watched and then asked, “Do I need to take off mine?”
Smiling I said, “Oh no, it’s okay, it’s up to you,” and as I went over to turn on the TV, she reached down slipping off her flats.
Kaitlyn eventually followed me more into the living room, and when I tried to suggest she sit on the couch, subtly motioning that way, I asked, “Where would you like to sit.”
I wanted to be able to sit by her, and being it was a large sectional, with plenty of room to ... um, mess around, I sat kind of in the middle. Smiling, she moved over and as she sat on the longer side, I subtly scooted over, moving to sit by her. I made sure to not sit right next to her, but it did make her nervously move over just a little bit.
Still, I was able to sit close enough and after taking a drink off my beer, I sat it down on the coffee table and then reaching over, I took her hand. Looking at me, I smiled and wanting to give her a kiss, I took her beer and after setting it down, I lean toward her. At first, Kaitlyn smiled, but she looked hesitant, and when I moved a little closer, she instinctively closed her eyes.
Smiling, I put my hand on her thigh and as I pressed my lips against hers, I moved my hand up to her waist. It was just a simple kiss, but we did end up kissing a couple times, and when she leaned against me, and we hugged, holding each other, I kissed her on the head.
She seemed relieved in away, I know I was, and smiling to myself, I hoped she be okay with being with me again, but really, I wanted to get her in bed, “But how?”
I didn’t want to appear overzealous or overly anxious, but I was, and I felt there was definitely a chance, and as we held each other, she looked up at me and suddenly said, “This is nice.”
Knowing we were both probably a little tipsy, I smiled and laid her back. It too made her smile, and when I laid her to the side, and immediately moved on top of her, I again gave her a kiss.
Kaitlyn’s hands had moved to my sides and when I brought my one hand up past her open flannel shirt to feel on her chest, she immediately opened her eyes. Her boobs were definitely bigger, firmer, probably because she had put on weight, but they were more fleshy feeling too, and as we continued to kiss, I casually tried to bring my one hand up under her tank top.
I wanted to feel them, but as soon as my hand was right under her one boob, she reached up, and blocking me she said, “Wait!”
Looking at each other, I moved my hand down to her waist, and when she said, “Let’s not go too fast,” I smiled knowing I still had a chance, a chance to again get her in bed.
Lifting up off her, Kaitlyn said, “Don’t be mad, okay.”
Smiling, I told her, “Never,” and then said, “I like you,” and then after a few seconds I said, “I’ve thought about you a lot.”
It made her smile embarrassingly, and then leaning up, she kissed me. I still knew she was a little hesitant, but I still felt she was wanting to do it, and when I leaned her back again, and I brought my hands up to feel on her chest through her tank top, she didn’t stop me.
“Oh my god,” being with her again had given me a hard on, and wanting to keep things going, I tried inching her tank top up. However, Kaitlyn again stopped me, and being I really didn’t want to stop, I moved my hands to her waist.
Looking at her, I casually slipped my fingers inside the band of her legging and when I tried to subtly peel them down, she brought her hand up, and smiling, pushing on my chest, she asked, “What are you doing?”
Kissing her, I sat up and as she too rose up, she again said, “Don’t be mad.”
Smiling, still feeling I had a chance, I patted her thigh, and after a few seconds of us sitting there, she put her hand on my leg and asked, “What are you thinking?”
Again I smiled and said, “I like you a lot, Kaitlyn.”
Smiling at me, she again gave me a kiss, and not wanting me to feel she didn’t want to do it, she casually slid her hand to my crotch. I was hard, and I’m sure she felt it, because she looked at me, and smiling she took hold of it through my pants, and asked, “Do you have a hard on?”
I could feel myself blush, maybe a little embarrassed, and when she gave it a squeeze, and then suddenly stop, I leaned her back again and immediately tried to get her leggings down. I wanted her to know that I wanted to make love with her again, and when she again stopped me, I smiled and asked, “Do you wanta go to my bedroom?
She didn’t respond right away, but smiling, she gave me a shy little nod. Smiling too, I immediately moved my hand down to feel on her crotch and feeling she didn’t have anything on under her legging, I stood up. Taking her hand, I pulled her to stand too, and as we stood there for a moment just looking at each other, I smiled and asked, “Are you ready?”
Seeing that smile of hers, I turned and as I started toward my bedroom, I could sense she was still hesitant. However, she followed me, and as we went through the doorway, I turned to face her.
I decided to not turn on the lights, because I felt she would feel more comfortable, and really there was still plenty of light sneaking in from the hallway. Looking at each other, I smiled and then pulling her close, holding her, I asked, “Are you okay?”
Seeing her nod and then giving me a smile she leaned up to kiss me. Smiling, I closed my eyes, and as our lips again pressed against each other, I grabbed her waist and then sliding them down, I reached behind her, grabbing her ass. It was so nice to feel her again, and really her shapely ass felt firm in those leggings. We eventually stopped kissing, and as we looked at each other, I took her hand and led her closer to the bed.
Still looking at each other, smiling, I backed her against the bed, and then as I casually reached up and pulled the covers back. Seeing me do this, I felt there was still a nervousness she was feeling, and wanting this to go well, I kissed her and pushed her against the bed some more.
Kaitlyn was leaning back, and putting her hands on the bed, supporting herself, I moved to lift her up on the bed. Yea, she was heavier, but really not too much, and smiling, knowing it was going to happen, I gave her a kiss and immediately tried to get her flannel shirt off her shoulders. She didn’t stop me, but instead helped me get it off and after dropping it to the floor, she self consciously looked down at her chest. Looking down at her chest too, I couldn’t help but stare and smile, seeing how full her boobs looked in that tank top.
She wasn’t wearing a bra, but the tank top she had on, had a little shelf that helped support her tits, and seeing her little nipples pressing against it, I reached my hands up to feel on her boobs. She again didn’t stop me, and when I gave her a kiss, and tried to peel her top up over her head, she simply smiled.
“Damn it,” her tits hung up in that little shelf, but quickly I figured it out, and after getting her tank top over them and seeing her boobs over flowing, I looked up at her. She again looked a little self conscious, with me looking at them, and not wanting her to feel that way, I smiled and Immediately took my shirt off.
Yea, I know I was older and maybe little out of shape, no matter how much I tried, but it did brighten her face, and smiling, seeing my chest, preoccupied as she fixated on it. Smiling too, I now unbuttoned my pants, and after getting them unzipped, I pulled them open slightly.
Kaitlyn was watching intently, obviously wanting to see, but when I tried to again get her legging peeled down, she again reached down stopping me.
Looking at her, I had her scoot up on the bed some more and as I climbed on top of her, she unknowingly spread her legs. Pressing against her, thinking, “How am I going to get her leggings off,” I moved down to feel on her tits.
Going down, I started tonguing and sucking her pink little nipples, and then as I moved down more, again trying to peel off her leggings. she took a deep breath.
Getting them down part way, she guardedly lifted up, and as I got them passed her shapely ass, I hurriedly pulled them down. Seeing she wasn’t wearing any underwear, I looked up at her thinking, “Oh my god.”
I couldn’t believe it, but wanting to see her pussy, I again casually glanced down. Smiling to myself, seeing her neatly trimmed blonde pubic hair, plump mound, and young pink little slit, I put my hand on her pussy. Looking up at her, gently massaging her pussy, I smiled awkwardly. Kaitlyn too was looking down, watching for my reaction, and even though I tried to act as if … well you know, I couldn’t help but look up smiling.
Taking my hand off her pussy, I continued to work to get her legging down over her feet, and after dropping them to the floor, I again glanced at her pussy. I really didn’t want to appear overly anxious, and even though I was, I simply slid off the bed and quickly tried to get my pants and my boxers off.
Again, I could see Kaitlyn straining, wanting to see my cock, but when she got a glimpse, she looked up smiling, catching herself gawking. Smiling too, I moved closer to the bed, and when Kaitlyn leaned to one side, trying to reach for my cock, our eyes met.
Helping her, I held my cock out, and smiling she swung her legs, turning to eventually lay on her stomach. She was leaned up on her elbows now, and when she took hold of my cock and started stroking it I thought, “Is she,” but before I could finish my thought, she looked up at me and after inching closer, she suddenly took my cock in her mouth.
I couldn’t believe it and, “Oh my god,” watching her sucking my cock and seeing her back and shapely ass was making me even harder.
I wanted to fuck her and looking at her ass wiggle as she sucked my cock, I gently started thrusting my cock in and out of her mouth. I wanted to cum, but wanting more than just a blowjob, I backed away.
Lifting her head up, Kaitlyn immediately looked up and asked, “What’s wrong?”
Smiling I leaned down and after giving her a kiss I said, “That felt too good.”
She too smiled, and when I had her swing back around and lay on her back, I think she understood.
As Kaitlyn lay on her back now, I climbed up on the bed and when I got back on top of her, I gave her a kiss and smiling I said, “I wanta …,” but before I could finish my thought, she kissed me.
Pushing my cock into her crotch, she squirmed a little, obviously wanting to get more comfortable, and wanting to fuck her, I gave her a serious look and asked, “Do you, want me to use a condom?”
She was hesitant, thinking about whether we should or not, and then looking at me cautiously, she eventually smiled and said, “No it’s okay, unless you want to.”
Smiling too, I leaned up and after a kiss, I moved down, sucking her neck again. It was only briefly, and wanting to taste her, taste her like the last time, I moved down more. Kissing my way down until I was between her legs, she suddenly arched up in anticipation.
Fingering her full little pussy, spreading her lips, I immediately went down, and closing my eyes, I dipped my tongue in her slit. She was wet and the mustiness of her pussy was a turn on, and as I continued to lick at it, flicking her clit, I wanted to be in her.
Moving back up, I immediately reached down, and grabbing my cock, I tried to push it into her. She was so tight or maybe she was tense, in either case, it was difficult. Moving the head of my cock up and down her wet little slit, hoping she’d relax, I again tried to push into her. “Oh yea,” I was in her, but just a little, and letting go on my cock, I gave her a kiss and asked,”Are you okay?”
Smiling, she wrapped her arms around my neck, and when I pushed into her more, she instinctively pulled away a little. It felt good to be in her, and after again asking if she was okay, I tucked my arms up under her shoulders.
Giving her a kiss, I pushed into her a little more, and when I felt her take a deep breath, I slowly started trying to move my cock in and out of her, fucking her. She felt so good, tight and warm, and as I started fucking her a little faster, I wanted to cum.
Holding her, fucking her, breathing hard, I could feel it, “Oh my god, I’m gonna cum,” and after a few deliberate thrust, I blurted out saying, “I’m gonna cum.”
Holding her, pulling her close, I again started quickly pumping my cock in and out of her. Kaitlyn’s hands were now on my sides, and feeling, “I’m going to cum,” I pushed deep into her.
Holding her, I let it go, and as my cock bucked inside her, I felt myself stiffen, and again thought, “Oh my god.”
It felt good, and as my cum continued to pump, spilling inside her, I again started to slowly move my cock in and out, subtly trying to fuck her again.
I know she had to feel it, it was a lot, and when I stopped and we kissed I asked, “Are you okay?”
Looking at her, she smiled and as she moved her arm up to hug me she said, “Yea, that was great.”
Holding her too, I again kissed her, and then scooting down, I let my cock slip out of her. It had already started to go limp, and after kissing her chest, I looked up at her. Kaitlyn was smiling, which made me smile too, and when I moved, lifting up off her, I looked down t her pussy.
It looked a little red and definitely swollen, and seeing cum seeping out, I rolled to the side, laying next to her.
We were both out of breath, but it was so nice to be with her again, and with my hand touching her thigh, she reached over, putting her hand on mine. Laying together, trying to catch our breath, I sensed she was maybe having second thoughts about what had happened, and after a little bit Kaitlyn said, “Maybe, I should get going.”
I should have known this would happen, and after patting her leg, and rolling to face I politely said, “You can stay,” but I could see she was hesitant.
I’m not sure why, and I really wanted her to stay, but figuring she was still concerned about the difference in our age, or maybe subconsciously she was thinking about her failed relationship. In either case, Kaitlyn eventually got out of bed, and after gathering up her clothes off the floor, she went into the bathroom. “Oh my god,” I thought, “I wanted her to stay,” but how can I convince her.
It was late, way after midnight and wanting to at least walk with her to the front door, I too got part way dressed.
As she came out of the bathroom, I met her and after giving her a side hug, I asked, “Sure you can’t stay?”
I think she was thinking about it, but seeing she had already decided to leave I again said, “It was really nice to see you again.
It did make her smile, and we did hug, but I could see she wanted to leave. At the front door, she told me, “I had a good time,” and after giving each other a parting kiss, I let her leave.
Closing the door, I went back to my bedroom and laying there, I smiled thinking about what we had just done. I could still smell her perfume on my sheet, and seeing a small wet spot, I found myself feeling on my cock, and wanting to be with her again, I grabbed my phone and sent her a message saying, “I really had a good time,” and then asked, “ I hope we can see each other again.”
When she didn’t respond right away, I figured it was because she was driving, but as time passed, I thought like last time, “It wasn’t going happen again,” and then realized having sex with me was her way to rebound.