*If you are interested there is some [background](https://www.reddit.com/r/gonewildstories/comments/4ebsdp/finally_getting_to_meet_my_online_milf_precursor/) to how things started*
The days leading up to Rachel arriving we spoke a ton throughout the days. She seemed really anxious and excited as did I. I wouldn’t admit it to her at the time, but I was also feeling incredibly nervous. For one, I wasn’t sure the confidence I had shown while we chatted/skyped would really translate to in person. I also wasn’t sure how I’d stack up to her expectations, her being older I’m sure she had many experiences, both with her husband and by dating before him. I just kept trying to tell myself all I had to do was be myself, that was enough to get her to visit, so it’d be enough to win her over so to speak.
Her flight was to arrive early evening on Wednesday and she was going to be flying back out Saturday afternoon. I offered to pick her up at the airport, but she suggested we just meet at the hotel. The plan was for her to get there, check in, get situated, call her husband then for us to meet in the lobby. We’d get something to eat then take it from there. I don’t really have PTO per se, so take days off for me wasn’t as simple as just scheduling PTO days. As soon as I knew the plans I worked longer the beginning of the week, trying to meet some deadlines before Wednesday night so I could be out of the office Thursday and Friday. The combination of anxiousness of Rachel visiting and panic of not being able to get everything done for work I needed to was exhausting. I had to get someone else to sign off that I had everything done before checking out for the week. Tracking that person down on Wednesday seemed like such a pain in the ass. I had plans to leave the office early on Wednesday to kinda relax some before heading to the hotel but that didn’t pan out. By the time I finally got the sign off I was running up against the time I told Rachel I’d be there. I raced home, showered, changed and raced over to the hotel. This did absolutely nothing at all to calm down my nerves.
The hotel she was staying at was pretty nice, one fairly close to the airport. I parked in the lot and just sat in my car. By now, between racing to get there and just being otherwise nervous/excited/anxious, my heart felt like it was about to beat out of my chest. I was trying so hard to just calm myself down, telling myself this was no different than any other date. That everything was going to go fine. That we already got along great so all I had to do was be myself. Of course, none of this helped.
Finally, I get out of the car and walk into the lobby. I really had only felt nerves like this a few times in my life. I felt like my knees were wobbly, my heart was absolutely pounding. I was just praying that I wasn’t also drenched in sweat, but by the time that thought popped into my head I was in the lobby and too embarrassed to look. I also had zero idea of what I should wear. It was fairly cool out, so I had on a pair of black regular cut dockers and a dark blue collared shirt. I’d say it was maybe just a bit too casual of something you’d consider business casual. I was hoping it wouldn’t look like I was showing up for an interview, but also wouldn’t look like I just got up off the couch and rolled in there.
The lobby was fairly large and had a few areas to it. The receptionist desk, a little computer station, a buffet area, common area with a few couches, entrance to the restaurant and a few hallways leading off of the lobby. As soon as I looked into the area with the couch I saw Rachel sitting there. She got up with a big smile and walked over. She had on some rather tight dark blue jeans, a snug red sweater that dipped low enough in the front to show the very top of her breasts and a pair of heels. After smiling back and walking to her I could help but let my attention drift down to her hips and thighs. In those jeans it was amazing how her legs looked. Her thighs brushed against one another as she walked, but they looked so firm and had the most amazing curves to them. As I said before, she had a thicker figure, but in those pants she had such gorgeous curves. If there was any chance of me to get any harder, it would have been eliminated after watching her walk towards me.
“Michael!!”, we finally got to one another and she wrapper her arms around me over my shoulders. I reached out with my arms wrapping around her waist as we pulled one another against ourselves. Even fully clothed, that first moment having her body against mine…this woman who I’ve gotten to know so well, played with, would cum for, masterbate with, this woman I’ve viewed as a friend, maternal figure, lover, someone I’ve shared personal details with and who has been open to having her share the same….in that moment I felt like I was going to lose it. Her beautiful breasts pressing against my beating chest, my painfully hard erection pressing against her stomach. Fuck, the moment had finally come for us to meet.
We hugged there for a moment before she pulled her head back and looked up at me slightly, sliding a hand up the back of my neck behind my head to pull my mouth to hers for a kiss. Our parted lips pressed together then for a moment our tongues brush against one another before the kiss is over.
“God, can you believe it’s taken this long to finally meet??” She sounds so excited and genuine.
“Wow, so long.” In my head I’m thinking I sounded like such an idiot there. My nerves were races and I really couldn’t put together anything more coherent than that. I just smile into her eyes.
She can’t stop smiling and seems a bit giddy. “Don’t be nervous! You’re going to make me get even more nervous than I already am!!” She laughs a little as she’s saying that, almost taking that playfully motherly scolding tone when she says that.
Hearing she’s nervous helps calm me down some. I admit my heart is racing like crazy, which admits as well. Getting it out there helped a ton. We were both nervous (for reasons both common and different) so why not get something to eat and just talk. A bit reluctantly, I place my hand on the small of her back as we head towards the hotel restaurant. My hand just above her ass. As soon as my hand touches down she leans towards me a bit. In my head, all that’s bouncing around is “What the hell is going on.”
Neither of us really ate a whole lot for dinner. I just ended up getting an appetizer and Rachel got a salad. We had a few drinks as well. Initially the conversation was rather benign, some compliments being exchanged, talking about shared interests, some playful sarcasm. Once we were done eating we decided to hang at the restaurant for a little while longer to have another drink. I wouldn’t say either of our nerves were completely calmed (mine certainly weren’t), but things seemed much more relaxed than they did initially. It was starting to feel as it had the times we spoke online.
Either by slip of the tongue, the alcohol, or a growing sense of comfort I was the first to advance the conversation.
“Watching you walk over to me had more of an impact that I thought it would” smirking some as I said it.
As she smiled back, “Just going to leave it at that?”
I laughed.
“Sure, you can leave it up to my imagination, but I’d much prefer hearing it.” This time her smile looked a bit more serious.
“Watching your legs…I couldn’t have gotten any harder. It was almost painful.” I said it, but immediately afterwards felt kinda shy about it. I just smiled and kinda laughed as I took another sip of my drink.
“So I noticed, was hard to avoid when you were pulling me against you.”
The playful, and sexual, banter started. We sat there for a little while longer going back and forth. Things now had definitely fallen more inline with how we spoken online. It also became clear our time there was done. I paid the tab and we headed out. Walking out my hand again fell to the small of her back. This time though, I let it fall lower, gently resting on one of the cheeks of her firm, thick ass. We stopped for a moment in the lobby.
“Should we, um, go up?” I swear I started out sounding confident then the nerves kicked in half way through.
“Might as well, otherwise this is a long way to come just for a dinner.”
We get into the elevator and that was it. The nerves, anxiousness, excitement, horniness all came to a head. We started kissing before the doors shut and I got her against the side of the elevator. Or tongues stroking one another as her hands reach up to my chest. Her nails slightly digging into me as she grabs on my pecks. I reach behind her and take full grasp of her ass. Feeling her cheeks flex as I grab them firmly, slightly pulling her up as I push my raging hard cock against her. It felt like we were going at it like this for a while, but a few seconds later we here the ding of the elevator for her floor.
We get out and walk down the hall to her room. She pulls the card from her pocket and opens the door. No sooner does the door shut before we continue form the elevator. It’s almost like I’m hyper sensitive to everything about her. The taste of the gloss on her lips, the smell of her perfume, ever single soft moan that escapes into my mouth as we kiss. My hands leave her ass and slide up under her shirt. Drifting over her stomach, up towards her chest, finally reaching her breasts. My fingers pull back up over her bra and gently (or as much as I could in the moment) start to rub her breasts through her bra. She had by far the largest breasts of anyone I had been with, they felt amazing.
Finally her experience I think started to kick in. She broke off the kissing and, falling back to that maternal tone of voice, suggested we slow down as she smiled. She began to unbutton my shirt, undoing the last button then sliding it over my shoulders. Looking down at my chest and abs she moaned a bit before dragging the tips of her fingers from my pant line up over my stomach to my chest.
“Oh baby,” she leaned down and started to kiss my shoulders then my chest. her hands stroking my abs now. My cock was throbbing having her hand so lose as she took her time kissing my bare chest. She sucked on my nipples for a moment and I immediately let out a moan. She was so intently focused on kissing every inch of my skin. By now my boxers had what felt like a huge wet spot forming.
She pulls herself away and pulls her sweater up over her head and throws her hair back. Seeing her breasts lofted up in her lace black bra. She smiles as she reaches up and slowly pulls the cups below her breasts, allowing them to fall freely. I don’t event hesitate as I lower my mouth to her breasts, slowly going back and forth between them. Kissing each with large open mouth kisses. My hands stroking her sides as I work my mouth towards her nipples. Her fingers go through my hair as I hear her moaning. I get to one nipple and run circled around it with my tone, sensing her squirm some. Then finally sucking it into my mouth. Her other nipple between my fingers as I give it a soft squeeze.
“Oh fuck, baby boy.” She lets out the loudest moan yet. She unbuttons her pants and trying to tug them down past her hips, swaying back and forth some as she fights to get them down. My attention is now drawn elsewhere now. I kiss between her breasts and down over her stomach as I drop down to my knees. I nudge her hands aside as I hook my fingers inside the waist of her jeans and tug them down. They don’t go down easy as they fight past her thick ass, then practically pealing them off her thighs. I look down for a moment and see her matching lacy black g-string. I go back to kissing my way down her stomach as I push her jeans down further.
Taking a step back now. Throughout the time we had spoken online there developed this shift in the dynamic between us. In the beginning I had been my typical assertive self online when speaking with women. That’s not to ass I was a bully, or spoke down to them, or was abusive or anything. But I was always more of the dominant one. Looking back it probably was the case that I was focused on my own needs before the person I was speaking with. I think Rachel identified that early and wasn’t so thrilled with that idea. She called me out on things like that, kinda keeping me in check. Over time I really considered her to be someone who deserved to be taken care of, not inspire of my own needs and desires, but certainly not as an afterthought either. There would be times when it was just about her, which previously I would have never imagined would have been the case.
Back to the current, I think all that “work” she had done laying the groundwork started to pay off. Where as with other girls I had dated I would have been most interested at that point in getting my dick sucked, having her jerk me off or sex, at that moment I wanted nothing more than to taste her. Here I was, still in my jeans, kneeling in front of her as she was not just in a g-string. I passed over her pussy and kissed down her thighs. I loved how wide they were how smooth, how firm. Rachel continued to moan softly, her fingers running through my hair as I finally got her jeans to her ankles. Her other hand reached between her legs up to her g-string, cupping the side of it and pulling it over, exposing her beautiful, lips, and smooth, bald mound. She leaned back against the wall, lifted her one leg and laid it over my shoulder.
She didn’t say a word, she didn’t have to. Even if she did I think I would have had my lips on her before she even said what she planned on saying. I reaching up as I raised up onto my knees, grabbing onto her hips the same moment my lips pressed against her wet pussy. I immediately kissed her lips and tasted her for the first time. My tongue pressing against her lips then dragging it upward, the tip passing along slit all the way up and finishing by circling her clit. I started to eagerly lap my tongue against her lips. While this is happening I can actually hear her gasp before the “Oh fuck!!.” She slaps her hands against the wall to help keep herself up as I feel her weight all fall upon my face and shoulder. It was a struggle to keep her up and she soon pushed my head back. At first I panic and thought I was doing something wrong, or maybe she was having second thoughts. She just stood there out of breath, panting as she pulled her hair away from her face.
“It’s too hard like this.” She walked over to the bed. I stayed kneeling there, hypnotized by the sight of her ass. Seeing how the g-strong disappeared in her thick round ass, watching each check bounce as she walked. Finally she sat on the edge of the bed and told me to come over. I got up quickly and walked over, standing in front of her. She unbuckled my belt, then unbuttoned my pants, then unzipped them. Her hand that close to my cock almost got me off. She tugged on my pants just enough to let them fall to my ankles. I stood there in a pair of gray boxer briefs, my cock fighting as hard as it could against the briefs. There was a very obvious and very large wet spot that had formed at my head. She smiled and reached down, running her index finger over the wet spot. Her chest still heaving as she tried to calm her breathing down.
“I want you to finish what you started,” she looked at me smiling. At that moment my head was a mess so I wasn’t sure what exactly she meant by that, until she placed her hands on my hips and nudged me down. I got back down on my knees in front of her. Eye level with the bed. Looking up her thighs as she parted them more to her gorgeous, bald pussy. She was wet enough now it almost glistened some. I put a hand on each thigh, gripping them tight and spreading them apart as I dropped my mouth back to her pussy. I couldn’t get enough as I slide my tongue repeatedly between her lips. Her juices coating it. Occasionally wrapping my lips around her clit and sucking on it, pulling it into my mouth and flicking it with my tongue. The longer I ate her pussy the more I could feel her juices collecting on my lips, my chin, all over my mouth. The noises she was making were almost enough to make me cum. Fighting to keep her breath as she would start panting. She would have short, very intense moans followed by a longer one. As much as I wanted to reach down and stroke myself I was afraid to. I felt like anything more in that moment and I would cum.
Her hand reach down and cupped behind my head. “About to cum.” She pulled me in hard against her pussy as I focused on her clit. “Oh my God baby boy,” she almost sounded like she was whining. Then her thighs clamped around my head and she started to buck. She thrusted her hips up, pushing my head up with them and holding it there. Letting go of my head she smacked her hands to the bed and was up on her tippy toes. It sounded like she wanted to say fuck, but just kinda squealed. I kept sucking on her clit and flicking it with my tongue. Finally the initial surge ended. She put her hand on my forehead and tried to push my mouth away. “Ok, ok, ok, stop baby.” I could tell just how intense this felt for her now. I reached up under her thighs, wrapping my hand around the back of them and curling my fingers along the inside of her thighs. Holding my mouth against her as she tried pushing me away. She started squealing enough then eventually took her hand off my forehead and I could feel her cumming again. As she thrusted her hips her pussy rubbed all over my mouth, my chin, my nose. I had her cum all over my mouth by now. She was all I could taste, all I could smell. My cock by now was painfully hard. It was such an incredibly intense feeling.
As I sense her finishing I finally stop and she just drops to the bed. Taking fast, deep breaths. Her hair is a mess, half over her face. Her pussy, and everywhere around it is wet. Her face is completely red. She’s still clenching onto the comforter of the bed. I stay on my knees there giving her a moment. I just start to kiss her thighs softly. She takes my hand with her, interlocking our fingers and pulls me up towards her on the bed until I’m laying beside her.
“My baby boy…OMG, that was…” She’s still panting I reach out to her breasts and and gently play with her nipples for all of a second before she pulls my hand aside. “Not yet. I can’t. I’m just…I don’t know, it’s too sensitive.”
I question her, “your nipples?” She tells me everything is just tingling. We are just laying there, I’m perfectly content in that moment just looking at her body, seeing the effect I’ve had on her. I think she realizes it’s all been her up to that moment and suddenly roles over onto me. I’m on my back, she’s straddling my thigh, her chest half on mine. She pulls my face towards her and we start kissing. These were such deep, intimate kisses. Each one lasted long. I could feel her grinding against my thigh as it got more and more slick from her cum and my saliva. She reached down and finally wrapped her fingers around my cock through the boxer briefs. I just gasped. I felt like if she did anything else right then I was going to cum. I just instinctively reached down and held her hand still.
In a soft voice she asked, “Are you close?”
I was pretty embarrassed that I was. I didn’t want her to think I couldn’t last more than a few seconds. I kinda hem hawed around giving an actual answer.
“It’s fine. Trust me, I figured this would be the case.” I looked at her and she was smiling. “We have a LOT of time together and I know once you’re less anxious you’ll last longer.” It was amazing hearing her talk to me like that really put me back at ease. “Seriously, I want you to come baby boy. There will be plenty more times”
She got off of me and kneeled down between my legs. Taking such care as she pulled my boxer briefs down over my cock, almost like she knew exactly how close I was. She had such a big smile as my cock sprung up once freed from my boxers. She started to stroke my body all over, except for my cock. Rubbing my thighs, my hips, my lower abs. Then starting to kiss all around my cock. The teasing was almost too much to handle. I just laid there looking down at this gorgeous, mature, woman…someone I really gotten to know and care about…kissing me so tenderly.
She looked up at me with a smile, “Ready?” I nodded. She grabbed the base of my cock and pulled it so my cock pointed straight up. Her other hand through her hair behind her head as she lowered her mouth. The moment before she wrapped her lips around my she looked up at me, her eyes focused on mine as she wrapped her lips around my head and lowered her mouth. I wish I could say that it took more, but looking into her beautiful eyes, seeing her on all fours between my legs, seeing her ass pointing up and watching my cock slowly disappear into her mouth was all I could take.
“Cumming…..” I grunted as I absolutely erupted. Her eyes got a bit larger as I started to shoot into her mouth. She kept her lips wrapped tight and slowly started to stroke as my throbbing cock pulsed. I could actually feel my balls pulsing as well with each shot. It sounds weird equating it to this, but it was so hard, so constant, it almost felt like I was peeing. My body was completely tense, every single muscle. This was the longest I could ever remember cumming. After what felt like an eternity I went limp on the bed. Rachel kept her mouth on my cock as she gulped down the mouthful then let me out of her mouth.
“Jesus, next time you better tell me if you are going to cum that much,” she said in a playfully scolding voice as she slapped my stomach gently. Her other hand didn’t leave my cock, just gently kept stroking it. She rested her head on my stomach, looking at my cock as she stroked. “What a beautiful dick.” I rubbed her back as she laid there beside me, head on my stomach, stroking. It really felt emotional at that moment.
Finally she spoke first, “I can’t believe this is happening.” She didn’t seem to be saying it in the sense of “wow this is awesome”, but more just kinda questioning it all, like I was. The initial sexual hyperactivity was gone. I was still really horny, but a bit more level headed. What were we doing? Was this wrong? Part of me felt like this had been some online fun taken a bit too far. But then I’d immediately go back to the fact that I really did have a strong attraction to her, not just sexually, but emotionally as well. We started to talk honestly, and it was actually pretty surreal. On one hand, there she was laying beside me completely naked, having just cum all over my mouth, and my cum having filled hers. But even so we really just talked about what we wanted, what this all meant, what could happen going forward. It was incredibly heavy and nothing I really imagined all the times I had fantasized about us meeting up. There was certainly the sexual connection between us, but I think that just really cemented the emotional connection as well. Following that talk things were amazing the rest of the time.