Let me begin by saying this was a situation that never crossed my mind as ever becoming a reality. I am a mid 40s guy, I do stay in very good shape, but I have never been that guy that women want to hook up with without getting to know me. My game was always built on being funny and charming and certainly I never get there on looks alone. I had a lot of travel time today so wanted to capture this with as much detail while it is fresh on my memory.
A recent business trip took me to the upper Midwest where one of my close friends’ daughter attends college. I have known this girl, let’s call her Savannah, since she was born. Her original dad took off when she was less than one years old and I played the role of Dad until her mom remarried (also to one of my other closest friends). To describe Savannah, she is a very bubbly, down to earth 23-year-old that dresses like a girly girl but acts more like a tomboy. She always talks to me about topics she did not want to bring up with her own parents and thus we built a pretty close relationship over her life.
My work trip was close to the town where the school she attends is located, a relatively smaller school still very much in the Midwest. I was going to be in town for the day for meetings, so I decided to fly out the next day to try and see her for dinner. After my meetings wrapped up, I checked into my hotel and texted Savannah to let her know I arrived. We made plans to meet at a restaurant close to campus but also by the downtown area where I was staying. Being a Thursday night, Savannah told me she was going out with her sorority sisters from school and it would be easy for her to meet me at this restaurant and walk over to meet her friends. About 7 o’clock I get to the restaurant and Savannah is already there waiting on me. Dressed in black tights, and ivory sweater (that still shows the majority of her butt), and brown riding boots, she has turned into a stunning beautiful woman.
Every time I see her it’s hard not to recognize how sexy she is. About 5 feet 1, sandy blonde hair, small on the chest but has an out of this world hips and butt. However, I put my good “Dad number two” hat on and try to be as focused on her as a person as humanly possible. She jumps up from the barstool, runs up and hugs me and gives me a big kiss on my cheek. While she is hugging me, she tells me how much she misses me and how excited she was that he could see me for a few hours. I tell her how much I missed her, how great it was to see her and what a truly amazing woman she is turning out to be. I even threatened to move there to protect her from all the out of control college frat boys that were probably chasing her around town.
We sit down to dinner, and she catches me up on her life in college, how her classes are going, how her circle of friends are as well as what she wants to do post-graduation. Then we start discussing trips we took as families in the past, different memories, things that made us laugh and things that made us cringe. She told me how much it meant that I was always there if she ever needed me, even if it was a question she was too embarrassed to ask her parents or she had too much to drink at a party in high school and then did not want to call her parents to come get her. Savannah starts laughing and asked me if I remember when she asked me what a rainbow party was when she was in sixth grade. I laughed, said I remember distinctly, as I about spit my drink halfway across the table at the restaurant we were at. To be honest, I had to look it up to make sure it meant what I thought it did. She just smiled and said she was always comfortable asking me those questions as I knew you would never judge me. I told her thank you and that really meant a lot and I’m glad I’m just been able to be there for her.
Our dinner ended and it was time for Savannah to go meet up with her friends. I told her I would walk with her over to meet her friends as there is no way I would let her walk by herself. Honestly, I was thinking how many chances will I get to walk around with a hot college girl in a college town. Savannah agrees, loops her arm inside mine, and we walk towards the bar area in town. Turned out to be a very short walk and Savannah’s friends are waiting for her outside this one specific bar. Savannah introduces me to her friends as “her other dad” that she was telling them about. All her friends are very nice and say they’ve heard great things from Savannah, and after a few pleasantries they go on their way. Savannah asked me if she’ll see me tomorrow. I’d say probably not as unfortunately I have a flight that leaves in the morning. Savannah frowns, then asks me if I have far to go to get to my hotel. I tell her not really as it is just a few blocks from the restaurant. She gives me a gigantic hug, big thank you for coming to see her, gives me a kiss on the cheek and then we say our goodbyes.
About 30 minutes before midnight, my phone starts buzzing. I look at my phone and Savannah is texting me if I’m still awake. I respond I wasn’t but for you certainly I will be. Savannah responds I don’t suppose you’d be interested in walking me back to my dorm? I responded as long as you don’t mind walking around with some old guy then of course. Savannah sends me her location and I go meet her in front of the bar. Temperatures dropped and I noticed Savannah didn’t bring a coat so I take mine off, put it around her shoulders and say I guess this is like old times but I’m glad I got the opportunity to do this as I don’t know how many more times you’re going to let a play in inning or two at this stage in life. She smiles, lays her head on my shoulder and says I was really hoping you’d be awake. I wasn’t ready for you to leave yet. Savannah then asks “are you really tired” to which I say “I just had a power nap so I’m good for a little while. What are you wanting to do?” She asked if we could grab a quick bite to eat as she could honestly use the food. I said absolutely and we walked over to a 24-hour, fast-food place as Savannah wanted the “grease” to offset the effects of the drinks she had.
As were talking about her night, she commented that her friends really liked me and two of them said that I was actually cute for a “dad.” I laughed at this and said “thank you for sharing as that’s not something I hear at this stage in life. Definitely that made my week.” Savannah smiles at me and asks if I want to know something else? She looks down, pauses and says, “I had a crush on you growing up, which does seem really weird given our relationship but then again we are not actually related so maybe it wasn’t so weird.” Not knowing what to say, Savannah quickly kept talking and asked me to remind her where I was staying? When I told her she said, “oh that is just a few blocks away and really nice”. I said “yeah, wasn’t far and I have a ton of status with that hotel chain, so they take care of me. They even gave me a two-room suite that I don’t really need.” Savannah perked up and said “really? OK then can I stay at your hotel tonight because I really don’t want to go back to my dorm room as I think my roommate and her boyfriend are there tonight.” I said, “that’s fine but do you need to pick up any clothes from your dorm tonight?” She said “no, I’m good I’ll just go back to the dorms and shower before class.”
Walking into my hotel, I tell Savannah she can have the room on the left. Her eyes immediately are drawn to the fireplace in the small living room and asks if we can turn that on as she is freezing. I say sure and Savannah steps into the bedroom while I work on the fire. After about a minute she comes out in just her sweater and curls up next to me on the couch. I started laughing a little and Savannah looks up at me and says, “you better not be laughing at me!” I smiled and said “no, I was just thinking there had to be dozens of guys hoping to take you home tonight and you end up with me. Not going to lie, I kind of enjoyed the looks I got from a few guys when we were walking back here. Definitely a look of how the hell is that possible! On that subject, how is the dating scene going for you?” At this point Savannah readjusts herself so her head is on my lap and says “it’s fine – just college boys that’s all. Good for dating but no one I am falling for. Most of them just want to hook up but have no idea what to do with a girl outside of get themselves off.” My curiosity jumps, so I ask “oh really. How so?” She explains that while she has hooked up a few times, she has yet to have an orgasm with a guy and thought she would have experienced much more by this time in college.” Realizing I am now giving her a light head massage, I say “I am sorry to hear that. Surprised to hear that actually. What are you hoping for?”
Looking up at me, she laughs and says, “mind blowing orgasms – Lots of them.” Almost to my horror, I have come to life as I feel myself stiffening, which unfortunately is next to Savanah’s face, and she can feel it to. With a really big smile, she looks at me and says “If that is for me that is so freaking cool. I would love to know I can have that effect on you.” Throwing in the towel, I say “Savannah, in complete honesty, I love you unconditionally and I hope you know that. I have watched you grow your entire life and couldn’t love you more if you were my own flesh and blood. Having said that, I am also male, and you are ridiculously beautiful and hot as hell. I have had to fight for years not to show any attraction to you, but I couldn’t be more attracted to one person than you.” As I stumble to keep talking, she lifts herself up and kisses me lightly at first, pausing to see how I would react. Within a few more seconds we start slowly but passionately kissing for a minute or two. Regaining my composure, I pull back and look at her and say “Clearly you know I want you, and not sure I could want any person more. I will not do anything to hurt you or hurt our relationship. Make sure you absolutely want this and if not that’s ok.”
She leans back in to kiss me for a few seconds, pulls back and locks in on me with her calming, brown eyes. With an almost serious expression, she says “I have wanted to do this for soo long. I have fantasized about this dozens of times.” I was genuinely shocked to hear this and trying not to blurt out what is wrong with you. I look at her, probably with a very surprised look on my face, and ask “Really?” Savannah pulls my head back towards hers to kiss me again, and after another minute she stops and whispers in my ear “Really. For a while.” I start kissing the side of her neck, working slowly from one side to the other and back to the lower part of her ear. I softly ask, “Can you tell me what happens in your fantasies?” Her breathing intensifying, she says “I always fantasized about you teaching me about sex. I have dreamed of you going down on me until I scream uncontrollably, of taking you into my mouth (and wanted to at the restaurant by the way), to having you teach me how to have an orgasm with different parts of my body. I have thought about everything!” Sliding my hands down her back until my hand is resting on her lower ass cheek, I am now out of my mind turned on as how incredible she feels. I look at her and say “not going to lie, you have the most insanely sexy body I have ever seen, and I have fought the urge to do this for years. Let’s work on your fantasies.”
I lift her up from my lap so I can move myself around behind her. I started kissing her on the back of her neck while sliding my hands across her breasts and down across her hips. I slowly help her lift her sweater off of her, noticing she did not wear a bra tonight (or had already taken it off). Running my lips and tongue down her back, I slide one hand in front to start massaging her clit. With one hand feeling how wet she’s become, I run my tongue across both sides of her ass, slide her black G-string to the side, then run my tongue down between her ass cheeks and slowly circle around the outside of her opening until she lets out a suttle scream. Savannah says, “wow that’s intense.” I’m now circling my tongue around and up and down her ass while sliding two fingers inside her to massage her G spot. Within a few minutes of this, I feel both of her hands squeeze tightly onto my body and she screams “oh fuck I’m about to seriously cum.” Within seconds I feel her body pulsating and she starts her orgasm, intensely moaning almost to a whimper, for about 45 seconds. After that she pulls me up and says, “oh my God that was amazing but stop as I literally can’t take it anymore.”
I reposition myself back up to where I can kiss and nuzzle on her neck and say, “I see you need to rest for a little bit but we’re just getting started.” She pulls her hands down and grasp both sides of my face and says “seriously, holy fuck that was awesome. What are you going to do to me next?” I said, “why don’t we pause for a few minutes and tell me another one of your fantasies.” She gets a big smile on her face and says, “why don’t I just show you.” She slides one hand down until it is resting on my now incredibly hard erection. She says, “I’ve always wanted to feel you” and then slides down off the couch. She takes both hands and unbutton my jeans and pulls everything off of me until I am now butt naked on the couch. She gets back on her knees, looks up at me and says, “now I want you to teach me how to suck your dick better than it has ever been done before.”
She quickly takes me into her mouth and starts sliding up and down on me like a woman possessed. I tell her to slow down for second, take one hand and slide it under my balls and gently massage them while taking the other hand and grip the base of my penis. I tell her to take her tongue and circle around the tip of my penis while slowly moving her hand up and down my shaft. I also tell her to take her tongue and run it up and down my shaft and then take my penis fully in her mouth and suck on it. Either she already has this figured out or she’s a quick learner, but she is now giving me an incredible blow job. Alternating between licking on me and sucking on me, she is doing a masterful job of getting me close and backing off just enough to play with me some more.
Realizing if I let her go at this pace, I’m going to end up spewing all over her in less than a minute, I reach down, gently grab her face and say, “hold on for a second.” She looks up at me and asks, “why did you make me stop” to which I said, “I want to show you something else.” I help her stand up then reposition myself to lie down on my back on the couch. I tell her to come straddle my face and then I pull her down onto me. With one hand on her ass, I slide two of my fingers on my other hand into her dripping womanhood. Savannah is completely shaven, which I absolutely love when going down on a woman. Running my tongue in and out of her wetness while also circling a finger on my other hand around her ass. This goes on for 5 minutes or so, her breathing become faster and more intense with each movement of my tongue. Savannah falls forward and braces herself on the arm of the couch. I feel her body tensing up as she screams “fuck please don’t stop I’m going to cum for you again.” I say, “let me know when you’re getting close” and she says, “I’m already there”.
I stop, tell her to stand up, turn around, sit back on my face and take me back in her mouth. I am hoping since she is already close that she won’t lose her orgasm trying to focus on me. As we get into a 69 position, she goes right back to working on my cock while I am running my tongue in and out of her pussy. Both my hands have a firm grip on her ass and I slide one finger down so it’s just inside her ass to see how she reacts to this. Savannah squirms a little bit at first, then stops sucking on me and lets out a few moans. She goes back to devouring me for another minute, then takes me out of her mouth and “says fuck I’m about to cum again.”
I stop and say “baby so am I. Where do you want me to cum?” She stops to look back at me and says, “in my mouth” and then takes me in her mouth and is stroking and sucking on me like its life or death. I bury my tongue back inside of her, running my hands up and down her ass as she’s dripping on me at this point. I have my hands so tight around her ass I realize that I had slid one finger almost all the way into her ass. Within seconds we both feel our bodies start pulsating as she covers me with her second orgasm while I unload into her mouth. As were both desperately trying to drive the other crazy while barely able to contain the intensity for ourselves, we stop and just lie exhausted on the couch.
After about five minutes, Savannah turns around, curls up and nuzzles up against my neck. She says, “holy shit that was awesome.” I said “well, hopefully that’s a good start to your multiple orgasms.” Savannah looks up at me and asks if she can kiss me? I smile at her and ask “of course. Why do you feel you needed to ask me?” She says she wasn’t sure given what we just did, at which point I pull her up and we lock into a deep kissing session for several minutes. I stop, slide my kisses over to her neck and up behind her ear and say “personally I love the taste of both of us together. For me it is incredibly erotic.” Savannah laughs and says “I wasn’t sure how I would react to that but wow I loved swallowing everything you had and knowing I could taste me on your lips. Guess that makes me weird huh?”
I put a hand on each side of her face so I can turn her head until our eyes are locked into each other. I kiss her again then say “there is absolutely nothing weird about that. You are an incredibly sexy woman learning what she likes and what she doesn’t. You telling me you loved that makes you even sexier, and I did not think that was possible. Way too many people go through life and never figure out things she is figuring out about herself now.” Savannah has a huge smile on her face, kisses me again for a few minutes, then says “You make me feel like I am perfect. You always have.” I kiss her back then tell her “That’s because you are. I am truly amazed and honored you are letting me have these moments with you.”
Savannah nuzzles her face against my neck and says “Um the thanks is all mine. You have given me two orgasms tonight and I got to do something I have wanted to do for years. I don’t think it’s fair that I am telling you my fantasies and you are not sharing. Have you ever fantasized about me?” Not sure how much I want to admit, even to myself, I kind of laugh and say, “to be honest I have had a few although I refused to allow myself to really go down that path, and even then only the past year or so.” Savannah immediately gets excited, as her voice raises, she says “ooh really, no way. Ooh, please tell me.” I stop to think if I actually do want to share this, but given we are both naked on a couch in a hotel I figure why not.
I look at her and say “for starters, I can’t tell you how many times you would be at my house in the pool, and I had to focus almost the entire time not to stare at you when you were walking around out of the pool. You would post pictures from nights out with your friends and always had on a tight dress and every time I had to fight the urge not to fantasize about what I would do to you if I was your age and met you out at a bar. I have desperately wanted to see you naked, to taste every part of you, to run my fingers across your body.” Savannah moves up and kisses me again, passionately, and we continue for several minutes, our hands running all over each other. I stop and ask, “seems like that was a good thing telling you that?”
Savannah smiles as she wraps her hand around my manhood now coming back to life. Still with an excitement to her voice, she says “I had no idea and God I love knowing that. I wish I knew. I thought about you definitely before you were letting yourself think about me. Now I wish I had called you for a ride home from a few parties. We could have done this much sooner. “I laugh and say, “well not too much sooner, you were off limits until you turned 21.” Giving me a sad face, she says “well, what I really want to know is what have you fantasized most about me?”
I take a deep breath then say, “you have no idea how much I desperately want to feel your ass slapping against me while I’m inside you.” She pulls up, kisses me moving her tongue around mine as deep as she can, then stops and says “I have fantasized about you fucking me so many times. You can totally have me anyway you want.” With a huge smile, I say “give me a few more minutes to recover but tell me was that the first time you’ve ever swallowed ?” She said, “yes and I loved every ounce of it.” I said “I am beyond honored that I was your first for that. Were you comfortable with me having my finger in your ass?” She said “that’s a very new feeling for me but it was so erotic. What is anal sex like?” I said “from my perspective, I can’t remotely get enough of your ass so the more I can feel it on me or be inside of you the better. From your perspective, it is tighter and more intense than regular sex and you have to go slower but you can get a very intense orgasm from it.” Savannah looks at me and says, “well then, you are going to have to fuck me both ways tonight.”
Apparently, I have been transported back to my own college days as I’m already rock hard again and truthfully, I feel like I could spend the next week doing nothing but fucking her. I slide my hands down her back, across her ass and say “your next orgasm is it going to be with me deep inside of you. My next orgasm is going to be in and all over your ass.” We instantly passionately kiss, our tongues almost fighting for air inside of each other. She reaches her hand down, grabs my erection and positions herself to slide me inside of her. I look at her as she put me inside of her and say “wow, I thought this would be strange in my fantasies, but this is seriously amazing.” As she is gyrating her hips on me, she says “I’ve dreamed of fucking you so many times and this is better than what I dreamed.”
After a few minutes, I can feel her breathing picking up again and then I lean forward to get up off the couch. On the wall next to the couch is a full-length mirror. I pull her over towards the mirror, have her face the mirror, position her forward and say, “now let’s have some more fun.” Sliding back into her I am living a fantasy I really shouldn’t be having but holy fuck she is sexy. I start pounding inside of her like a man possessed, watching her insanely curvy yet firm ass bounce against my body. Grabbing her hair with one hand and pulling her head slightly back, our eyes lock on each other through the mirror. I ask, “are you ready to cum on me with me inside of you?” Unable to move her hands from how hard I am thrusting in and out of her, she looks at me, breathlessly, and says “oh fuck yes please.” Within another minute I feel her body pulsating again and she starts to cum all over me. Sliding my other hand onto her ass I insert one then two fingers into her ass. I ask her if she’s ready for me to fuck her in the ass and she screams a loud “yes.” I pull out, and thankfully I carry travel packets of lubricant and grab a packet to make sure I didn’t hurt her.
After lubricating both the rim of her ass and my cock, I slowly insert the tip into her ass. She starts to squeeze her ass cheeks and I say, “let me know if this hurts you at all.” She says “no, it’s tight but it feels really good. Keep going.” I slowly move the tip of my cock in and out of her ass, gradually getting a little deeper with each stroke. Leaning forward, I take one of my hands and slide it under her stomach and massage her clit while I am slowly moving in it and out of her ass. Looking at her eyes through the mirror, I ask her how that feels and she says, “it actually feels amazing.” She then asks me if I liked it? I laughed and said “I am in absolute heaven right now. You have the greatest ass I’ve ever seen, and this may be the best fantasy come to life I will ever have.”
She tells me to start going faster and I start moving in and out of her at a continually increasing pace. Eventually I can’t keep my hand on her clit and I move back up and I’m now fucking her at a normal pace. She looks at me and says, “fuck that’s intense.” I ask her if she thought she could cum this way and she tells me she’s actually really close. I keep my pace steady, for another minute, slow down so I can put my hand back on her wetness to massage her clit.
After about a minute she screams “fuck I’m about to cum again!” I lean back up, firmly grip her ass with both my hands, pushing her ass cheeks close together and start sliding in and out of her faster and faster. She is constantly moaning as she starts cuming. I said “fuck baby I’m going to cum all over your ass” and within seconds I let my second load of cum inside her ass while basically screaming “fuck baby please don’t ever let this be the last time I get to do this.” While cumming, I pull out of her ass, slide my dick between her ass cheeks and finish cumming up and down her ass. I lean forward, and we both fall back on the couch tangled up in each other.
Both of us still breathing heavily, she asked me if I was serious when I said all those things about her? I pulled her face towards me, looked her in the eyes and said “I’ve never lied to you my whole life and certainly I’ve never been more open about my deepest feelings then tonight. More than anything, I just want to make sure you’re completely happy.” She leans in and kisses me again and says “you made so many fantasies of mine come true. I don’t know if this will ever happen again, but I wouldn’t change this for anything in the world. I will forever remember this, even more so if I’m masturbating in the shower.” I guess we were both exhausted as we fell asleep within minutes. Given how late we were up, Savannah missed her morning classes and I missed my morning flight but truthfully neither one of us cared. My trip did have to come to an end, we said our goodbyes and said can’t wait to see you next time. As I was boarding my flight, I got a picture on my phone from her showing her ass in front of a mirror, I think taken in her dorm room. With the picture she said “best night of my life, I can’t wait till you’re back there again!”
Source: reddit.com/r/gonewildstories/comments/y3e444/business_trip_m45_turns_into_surprise_hookup
This has been one of the best I have read in a very long time. Well written, the details are awesome to really paint the picture so they say. Well done!
Well written.
The crazy part is I don’t know many college females having Anal and especially how it unfolded 😂😭 this shit is just a story…
Kind of creepy!
tl;dr had sex
Savannah Sixx and Tommy Gunn
m8 up fa sho
This was incredibly hot, i tried to fight it thinking that’s a bit weird of him but that sounds like an amazing time. Definitely agree, very well written. This is the kind story I like to read. A little bit of wholesomeness if I can say that lol seems gentle but sexy. It really did it for me.
!updateme
She had drinks and you didn’t?
/updateme
!updateme
UpdateMe!
What about the shit sticking onto your raw cock after an impromptu anal?
!subscribeme
Very good story. Any updates
Great read very detailed and well written. More please.
What made this believable was that it was off after dinner but then she texted before midnight after she’d had a bit more to drink. The other part that made it believable was it was all under the mutual guise you were educating her. I thing older lovers , both men and women do not want to feel creepy. They don’t. But if they can honestly tell themselves “I’m actually teaching this young person and doing it right (like important usage of lube) then it frees up the older lover to have no reservations about new and different tricks in the bedroom.
Wow, very well written. Long but done in a way where you can’t stop reading and so captured in the moment. Definitely would enjoy some more stories. Great job!
!updateme
> “fuck that’s intense.”
> “fuck I’m about to cum again!”
> “fuck baby I’m going to cum all over your ass”
> “fuck baby please don’t ever let this be the last time I get to do this.”
> I pulled her face towards me, looked her in the eyes and said “I’ve never lied to you my whole life and certainly I’ve never been more open about my deepest feelings then tonight. More than anything, I just want to make sure you’re completely happy.”
Bro is living in a fantasy world watching too much porn and R rated movies 😂
!updateme
A very, very good read!
All I can think of after reading this is Woody Allen. Hopefully, this is entirely made up, because as bad as that is, it would be a lot worse if this is all true.
This was a great story. Lots of details, well written! VERY hot, I was rubbing myself the entire time I read it.
Very hot!!
“Thankfully I carry travel packets of lubricant”. This right here is where I started to notice this story is probably not true. Unless he is the most prepared 45M on a quick business trip, I just don’t see this happening. Anywho, mixed emotions about it. To each their own!
And he flew home to his wife and kids…
Hot story!
!updateme
Damn…hot!
Irishjui
!updateme
Post. Of. The. Year.
Great story. Is there more???
Wonderfully written. Regardless of the comments of it being creepy. Shoot your shot.