I have enjoyed masturbating to most of the encounters here on Gone wild stories I thought it was time to share this encounter. More than 30 years ago back in High School I had a classmate Bonnie she is a five feet tall long red hair light green eyes had a great personality and a fantastic figure complimented with a big pair tits. As a six foot tall slightly over weight nerdy teenager I used to fantasize and masturbate about her a lot . Even though we had many classes together throughout the our high school years I’ve never had to courage to ask her out, but we did become good friends.
After high school we lost contact, fast forward to a couple years ago we reconnected on Classmate the online year book. We then moved on to My Space, there is where I told her that I had a crush on her way back in high school. Bonnie asked me why I had never asked her out on a date back in high school, I just told her that was a chicken back then. We laughed it off and continue to reconnect online from there we moved on to Facebook.
For years after that we would keep in contact with each other on Facebook about everything under the sun and on rare occasion we would talk on the phone. We later on would get into some deep conversations about relationships. I was divorced at the time and Bonnie was going through some rough patches in her marriage. Bonnie would confide in me that Her husband didn’t pay attention to her any more. He didn’t like to go out more of a home body, she likes to dance he doesn’t. She asked if I danced I said yes and and feeling flirty I said I would love to dance with her but slow dance.Bonnie tells me how she has a dead bedroom now and confides in me how it is just her and her vibrator now and how she masturbates a lot.
Wow, this was the most intimate we’ve ever got, sensing an opportunity to possibly have this go somewhere much more hotter I tell her how being single for a year and that dating was tough so I also have to have to relive myself and masturbate. I tell her how I fantasized a lot about her when in high school and even now. She ask me about one of the fantasies so I tell her a recent one I dreamt up evolving slow dance with her slowly disrobing to the music and to us fucking. I get hard and pull out my cock and masturbate while I tell her the story.
The other end of the line gets real quiet I ask if she is playing with herself she tells me wishes she could but that her husband is in the other room and her vibrator is too loud and she didn’t want to get caught with her hand down her panties so she will use the story when she alone. Next day she tell me how she and her vibrator used the story and how dripping wet she was. From that point I was have a long distance extra marital digital affair with with my high school crush.
Bonnie had separated with husband and we were more freely to help each other mutually masturbate. Bonnie told me she was going to be in my town for a couple of days visiting some friends. Bonnie said how she would have a couple of hours before and we could do what ever we wanted before she met up with them. With a major hard on I made plans to pick her up at the airport when she flew in. She asked me to remind her how tall I was and I told her six feet tall she gasped and said that I would have to be gentle with her because of the hight difference. I assured her I would.
One evening I’m on the train heading to a friend’s house when I get a text from Bonnie telling me how she can’t wait and how horny she was, then she sends me a pic of her in a white dress shirt unbuttoned wearing a white lace bra, Instant hard on. Another pic comes in this time more exposed and I looking hard at the pic and zoom in, holy shit! is that a partial nip. Next pic full tit exposed, my mind is reeling all these years imagining what her tits looked like now
I’m riding the EL train with a raging hard on looking at her light pink silver dollar sized nipple. She tells me this was the first time she ever did anything like that. Later that evening when I get home I pull up the pic and start to relieve my raging hard on, I take a picture of my erect six inch pre-cummed cock and send it to her. Bonnie text me back that she is using the pic and can’t wait to wrap her lips around my cock.
The day finally came to pick her up from the airport my heart was beating so fast I could barely think. When I finally saw her she had looked almost exactly as she did when she was in high school.I greeted her with a big hug and a kiss on the lips. I took her to where my car was parked and in the elevator ride to my spot I gave another kiss but this time a little deeper. I asked her if she was tired from her trip when we get place she can take a nap. She said that she wasn’t tired and that she would be OK.
On the ride home we talked about what she was going to do while in town she was going to stay with a friend who lived not too far away from where I lived. When we get to my place I put on a little music I offer a drink we sat on the couch and started making small talk. A couple minutes go by when I go in to give her another kiss. At that point we start to kiss deeply, our tongues intertwined in a hot heavy make out session like we were teenagers again. I had gotten a major hard on and it was getting very hard sit and to concentrate. We take a break for air and then she asked for me to show around my apartment.
We get to the bedroom there she’s looking out of the window I come up behind her and I bend down to kiss her gently on the neck my hands go around the front of her waist and hug her tightly. The bulge my pants is pressing against her back that’s when she tippy toes and I spread my legs so she can presses her ass firmly on my crotch. Bonnie slowly grinds her hips so she can feel my cock against her round firm ass. My hands slide up and down the side of her body feeling her curves. she turns and tilted her head upwards as we kiss again.
We both move to the bed and lay down as we continue to make out. I unbutton Bonnie’s black shirt, revealing she is also wearing a black silk bra which make her skin more alabaster. Thankfully for me the bra had the clasp in the front and I was able to finally free those big beautiful tits and bring years of imagination and those pics to life. I am guessing that she was a 38C bordering D and her nipples were little bit bigger than a silver dollar almost flesh color a little bit darker than her skin. I took a moment to take a look at my teenage fantasy in the flesh finally. Bonnie’s large breast were heaving up and down and she breathed deeply. I lowering my head to her areola lightly licking it, making her nipple slightly contract and hard. I suck on her nipple and circled her areola with my tongue, Bonnie let out a little moan and my hard-on got even harder .
I am sucking one of her nipples my hand fondling her other breast slowly kneading and feeling the weight and firmness of her tit. I move my hand down to her pants. I unbutton her jeans to see she’s also wearing black satin panties. Bonnie lifts her hips up so I can take her pants off more easily, she sits up to take her shirt and a bra off when she sits up I can get a better sense of how big and beautiful her tits really are, I can really see how full and
firm her tits are. My fantasies did not do those beautiful tits justice.
Bonnie is topless on my bed and I can’t believe how lucky I am. I go back down to kiss her, my hands are gliding across her tits and down her stomach to her silk black panties. As my hand reaches her panties I can feel the warmth and slight witness from her crotch.
Bonnie lifts with hips up again and so I slide off the panties exposing her wet pussy. Bonnie notes that she is the only one naked that’s when I quickly take off my clothes. I move to get between her legs and she spreads her legs to expose her beautiful pink glistening pussy, Bonnie’s pussy is surrounded with a little bit of red pubic hair with a patch above. My first true red head.
I move down and kiss her inner thighs moving along to the outside of her pussy. I look up to see her smiling throwing her head back and gripping the sides of the bed in anticipation. Bonnie’s hips quiver a little as my tongue makes contact with her silky pink outer lips. Her scent is intoxicating, my tongue traces down from her outer lips to her hot wet inner lips. I curl my tongue and come back up the center of her pussy to her clit where I circle her clit with my tongue before I start to suck and taste a beautiful juices.
There between Bonnie’s legs I taking my time sucking, licking and enjoying her delicious sweetly drenched pussy. Bonnie moves her hip slightly up and down as I fuck her pussy with my tongue. Bonnie’s head is thrown back and her eyes are tightly shut, her breathing gets more and more heavier. I lick one finger and slowly parting her lips and insert my finger inside of her pussy gently working her G spot. Bonnie’s red pubic hair becomes matted down with the mixture of my saliva and her pre-cum.
I love eating pussy the taste, texture, the sent and the the pleasure it gives women. I am having a great time licking her silky pussy and finger fucking when Bonnie all of a sudden sits up and she grabs my head as she climaxes. I drinking up her delicious nectar digging my tongue deep to get every last drop. Bonnie opens her beautiful green eyes looks at me with hunger in them and says breathlessly it’s my turn. We get onto our knees in the middle of the bed, Bonnie strokes my engorged cock kissing deeply cleaning some of her own cum off my mouth.
Bonnie lays me down positions herself between my legs and lowering her head, her red hair falls to the sides I lift one side to watch her as she takes her tongue and tracing the tip of my now red headed steel hard cock a couple of times before engulfing my throbbing cock with her warm soft mouth. Bonnie takes almost of my 6 inches, Working her way down the shaft of my cock while her tongue is working it like an expert. Bonnie’s head slowly Bobs up and down eyes closed fantastically sucking on my throbbing cock.
I watch my High School crush work her magic on my cock my hands are on her tits lightly squeezing her nipples. Bonnie repositions herself to get more comfortable. I work my hand down to her pussy and insert a couple of fingers into her hot slit. While finger fucking her hot pussy I stop so often to lick my fingers, can’t get enough of her tasty pussy. Bonnie is working her tongue up and down the vein on my shaft when she lifts her head to ask if i like it, a small ribbon of my pre-cum from my cock to her lower lip glisten in the afternoon sun. I smile and tell her oh yes.
Bonnie goes back to pleasure my cock, the warmth and softness of her mouth greets my cock once more. All i can think as i watch her devouring my cock is that I am fucking my High school crush. Bonnie stops sucking and moves up and straddle my hips in a cowgirl position. Bonnie sits her drenched pussy lips my cock shaft, she starts to slowly grind her hips on my cock getting her wetness all over the shaft. I grab her hip and push her down more. Bonnie grinds her clit on my hard shaft the sounds of the wet lips on my cock are music to my ears.
Bonnie smiles at me and says if we should take a nap now, we both laugh and at that point she moves up on the shaft of my cock and my cock slides deep inside of her pussy. Bonnie gasps with delight her eyes rolling back and I exclaimed a little shocked to her that Wow! my cock found home really quick. I had wanted to put a condom on but at this point there was no going back I now. I was clean and she assured me she was clean and with that out of the way Bonnie started grinding her hips hard into mine, pushing my cock deeper and deeper into her oh so hot pussy.
Bonnie was moaning deeply eyes tightly shut I could feel the friction of her red haired pussy and my crotch hair. I wonder if my fire extinguisher in the kitchen is still working. Feeling the heat deep inside of Bonnie’s pussy was amazing. Her hands were on my chest and her tits were hanging low and slowly moving in rhythm with her body my hand moved up from her hips to cradle her heavenly tits. Bonnie is getting wetter as my cock slides deep inside of her, she and I get into a sexual sync.
My hands were on her ample tits feeling, squeezing, kneading them both and pinching her nipples. I lifted my hips up a little as Bonnie was grinding on me to get even deeper inside of her pussy if possible, this made her moan in a little bit more. I start sliding my whole now drenched with her wetness cock out of her and slam it back deep into her warmth, Bonnie lets out a grunt of delight when I did.
With both of Bonnies huge tits in my hands I squeezing them together, l lift my head and suckling on her tits moving from one nipple directly to the other. Bonnie lowers herself and puts hands to sides of my head, I release her tits letting hang to my chest and I slide my hands over her smooth body to her ass. My hand are all over her firm ass as she is riding me, I grip her ass hard. Bonnie’s eyes shut tight, her lip are pressed into a thin line and her head tilted to the side enjoying herself. Bonnie’s red hair is brushing my face and her huge tits brush up and down my chest as she is riding my cock. Every so often our nipples would graze each other as we are fucking which gives me a little more explosion of pleasure.
I switch up thrust and speed going from playing with her clit with the tip of my cock to exploring the deepest parts of her hot pussy. I feel myself getting close to exploding so I switch up positions and put her into missionary. I grab her hips positioning my cock which is now glistening with her juices and slide back inside her beckoning pussy lips. Bonnie moans her huge tits are swaying up and down as slide in and out of her. I love to watching women’s tits move like this when I fucking them and also in porn.
Bonnie’s pussy is now creaming up my cock and it looks like I’m turning butter. So I grid my hips deep, our hands are clasped together tight and and I lower myself to her feeling her beautiful tits on my chest. Bonnie is breathing more shallow her hip thrust get quicker and her eyes and face is tightening as she releases a wave of hot cum and my cock dips deep into her cum . Bonnie gasps for air opens her eyes smiles at me trying to catch her breath and mouths thank you. I tell her we are not done as I start for her next orgasm. The quizzical look tells me that no one she has been with before has has gone for that second orgasm that is just around the corner.
Knowing how some women get very sensitive after an orgasm I slowly work back into a rhythm. This time we lock eyes and she has a determined look on her face as I slowly work up to a ball slapping pussy pounding frenzy. Before I was enjoying every sexual sensation with that you have fucking a new woman, now I was on a mission to that second orgasm. Ponding her pussy now we start to work up a sweat. From Bonnie’s hands holding on to my back she slams her hands down a grabs the sheets as her brow furrows, I get to my elbows and grind our out pelvic bones together in a small circular motion.
I feel her hot breath on my neck as I breathe heavy and grunt and lower my head to suck on her ear lobe Bonnie starts to lets out little short yelps then to a long gasp to her second orgasm. Bonnie has a stunned look like she found something she never knew she could have. My cock is still hard deep in her as I feel the contraction of pussy slowly ease up.
I slide my hard cock out of her swollen red pussy very very slowly as she closes her eyes and softly moans. I give one more deep kiss while on my elbow before I layout next to her. I look at her my crush that i just crushed, my hand caressing her body but mostly her tits she is staring at the ceiling catching her breath. She looks over at me my hand are on her tit and says she wishes we could have done this much sooner and I agree as we make out some more.
We were making small talk enjoying the afterglow of sex when I ask her what time does she have to meet her friends she tell me and I tell her we have time for another round. She seems surprised she asked if I came, I told her no. So I position myself on top of her again and lower myself into her still wet pussy. The walls of her pussy pull my cock in, We kiss deeply as our hips grind we fuck for a good couple of minutes I push hard onto her pelvic bone she is coming close again but Bonnie tells me she wants to get me to cum also, so I break rhythm to bring her down and change position.
I get off the bed and pull her to the edge of it holding her legs up in the air I spread her legs apart watching her engorged outer lips and inner labia blossom like a beautiful dew covered rose. Gazing down on her body I place the shaft of my cock on her red rose and slide along her clit . I am holding her by her ankles being hypnotized by the movements of her tits. I plunge back into her swollen pussy and go for mine. Bonnie’s pussy lips form around my cock and move along as I thrust. Watching my high school crush laying out nude in front me with legs high in the air spread part and her big tit swaying my cock sliding in and out Bonnie’s pussy lip following the motion of my cock gets me close.
I tell her I am getting close to climaxing Bonnie then wraps her legs around my hips and takes control of the thrust. I ask her does she want me to cum inside or out of her pussy. Bonnie’s eyes are closed she doesn’t says anything or unwraps her legs. My final plunge let loose waves and waves of pleasure deep inside Bonnie’s pussy, she lets out a long deep moan. I let loose of my grip on her hips as Bonnie’s leg go from my hips and dangles off the bed to the floor. A smile runs along her face as my spent cock and a little of my cum slides out of her matted red haired pussy.
I make a mental picture of her laying nude there for later. Bonnie’s red hair spread above her, gravity pulling her huge tits apart to her sides. Bonnie’s almost ghost nipple still erect and Bonnie’s pussy slowly dripping a mixture of her cum and mine.
Bonnie gets up and on to her tippy toes and plants a big kiss on my lips and tells me she never came so many time as she did then. She turns and runs to the bathroom holding her pussy so not to spill any cum on the floor, she goes to take a pisses and then to the shower. I am tempted to join her in the shower as my cock starts to stir once more, but she has to go meet her friends. I drive her there we make plans to fool around again. Unfortunately at the time of this writing we have not gotten a chance to get together again. But l final got to fuck one of my high school crushes.
Source: reddit.com/r/gonewildstories/comments/5mmga8/after_thirty_years_i_finally_fucked_my_high
Nice story.