With Christmas upon us I normally make the trip to the midwest to spend time with family. This year was no different except that this year the drive would be from Seattle instead of Asheville. The big difference is the challenge of winter driving through Montana. It started off well with my husband and I loading the kids into the Honda Odessey and making it to Bozeman, MT the first day. We woke up the next morning planning to make it to Rapid CIty, SD and some fun for the kids at a waterpark there. We never should have checked out of the Bozeman hotel as we made it about an hour down the road on I-90 to see signs saying the interstate was closed. WTF? Blizzard without a snow storm? They call it a ground blizzard where the winds whip up white out conditions due to the cold temps and snow already on the ground. So we turned around and checked back into the Residence Inn in Bozeman. We thought we’d only be there a night but ended up being there two. The first day we hung out with the kids at the pool and made some new friends with other families also stuck there. Late into the first day I also met these two guys who had been working in Alaska and were trying to get home to North Dakota. We chatted a bit sitting in the hottub and ended it friendly making promises that if we stayed another night they were buying drinks.
The second night I found myself back in the hottub with my husband while the kids played in the pool. The two guys I’d met the night before showed up as promised with drinks and a festive spirit. I was game. I drank with them and we were soon becoming very fast friends and laughing up a storm. One of my sons wasn’t feeling well so my husband offered to take him back to the room and set him up for some couch time.
It wasn’t long until the talk in the hot tub turned sexual and as we were all getting pretty drunk no subject was off limits. One of the topics when I get drunk is that I’m a bit of a slut and have a husband that encourages it. That really lifted the spirits of the already rowdy hot tub. A couple other people came in, and I was forced to move over towards Matt one of my new friends. Matt unexpectedly lifted me on top of this lap, which surprised me, but the thought of moving never crossed my mind. I could feel his strong chest and arms around me, and also a rather large cock that was positioned nicely between my ass cheeks. Between all the drinks I had drank, the sexual banter, and sitting on semi-hard cock I was in a very horny mood.
As we sat there I would move my ass slowly, grinding against Matt’s hardening cock…the impact was apparent, his cock continued to grow and became very hard. He slowly reached around with his hand under the water and part the bottom of my bikini and began to rub my clit. I was in fucking heaven, it felt so fucking good I thought I would cum right then.
The moment was broken when Erick came up, but from his vantage point all he could really see was me sitting on Matt’s lap, and since everyone else was sitting on each other laps it appeared innocent. If he was pissed he did not show it, and simply chatted with me for a few minutes and said he was going back to the room and hangout with the kids. I knew he wanted a good cuckold story to come of this. He kissed me, and and said he would be back in a while…the whole time Matt was fingering the shit out of my cunt.
A small twinge of guilt hit me as Erick walked away and I thought “what the fuck am I doing over Christmas and the kids upstairs!”. I smiled back at Matt, and I excused myself to go use the bathroom. I needed to pee and it would give me time to mellow out and make sure this was something I wanted to go forward with.
Walking into the small personal bathroom I noticed the sinks and long mirror and my reflection in the mirror. My nipples were hard and visible thru the shear top of the bikini and my nipples very noticeable . After closing the door I removed my bottom and sat down to pee. I had barely sat down when the door opened and Matt walked in, he walked right over to me, pull his trunks down to expose a huge, beautiful cock. His stomach was tight and very defined and he had muscles like ropes that led down to his cock. He was closely shaved and his balls hung heavy between his legs. He was at least 8 inches and thick, so thick as I instinctively grabbed his cock my hand could not close around it.
I needed this cock, I wanted this cock and without a word or any thoughts of what i was doing I devoured it, swallowing the large mushroom head deep into my throat. He was so fucking huge I felt my jaw stretch and gagged as I worked him deeper into my throat, trying to relax to swallow more and more. He threw his head back and moaned out, and grabbed the back of my head forcing his cock back and forth in my mouth. I reached around and held on to his tight ass cheeks and continued to fuck him with my mouth.
I could feel him quivering, and as much as I wanted to have him cum in my mouth I needed to be fucked. I pushed him back, stood up, removed my top and walked over the bathroom counter. I bent over, raising my ass, and looked behind as he walked up to me, his dick swing back and forth. He place one hand on my shoulder as the other guided his cock into my soaking wet cunt. Without warning, or gentleness once his tip passed my pussy lips he shoved the entire 8 inches into me. I swear the whole hotel heard me scream, it was like taking a baseball bat, and I could not help but to scream “oh fuckkkkk”. He was very forceful, driving his cock so fucking deep in my cunt, hitting my cervix causing me to yelp each time. Oh God it felt so good I came hard, and quick…my legs shaking as he continued to punish my cunt.
I glance into the mirror and what I saw surprised me…it was a wanton slut taking a strangers cock, and enjoying every minute of it. Matt continued to fuck me and i came so many times I lost track, it felt so good I couldn’t help but moan, scream and beg for more. I was getting out of control not caring about what I was doing or who heard…I screamed ” oh fuck give me that fucking cock, fuck that cunt, fuck it so goddamn hard, make me cum again…oh SHIT!!! I could feel Matt tense, and with two more deep thrust felt him dump his seed deep in my womb….god he was so deep, it felt so fucking incredible.
I looked in the mirror as I felt his cock slip out of me, he had beads of sweat on his face and chest and a look of satisfaction on his face. I smiled at him in the mirror, turned slowly around and kissed him deeply on the mouth. I quickly put my bikini back on, kissed him once more and whispered in ear “thank you” and left him there in the bathroom.
I went back up to the room and the kids were happy to see me. I felt a little guilty but also knew I was happy and I had a good story for my cuckold hubby. Before the night was over and once the kids were asleep my husband encouraged me to go visit the guys in their room but that’s another story.
Kisses, Jen
Month: January 2017
First Trip to the Gym Makes Me want to go Back – MILF
This happened just last week. A female co-worker of mine invited me to go to the gym with her. I didn’t take any offense to it since I have gotten heavier than I was. I mean a 5’10” guy who weighs around 200 lbs (like me) could stand to lose a little weight and get in better shape. The only reason I think I still get dates are because of my blue eyes and sandy blonde hair that I keep cut just long enough to part and style a little.
The morning of our going to the gym came and I grabbed my bad I had packed the evening before containing my gym clothes and a water bottle.
Work was uneventful this close to the holidays as everyone is busier thinking about what they will be doing, gifts left to buy and things of that sort. My friend came in and took her place at the cubicle next to me. We will call her Shelly. She is cute enough and takes care of herself. She has shoulder length brown hair and light brown eyes. She dresses tastefully, revealing just the slightest amount of cleavage (yes, modesty drives me wild). I’d wager her beasts are 34Cs, and her body is pretty tight with a nice butt, but not too big.
The day moved on and we did our own things for lunch and worked on our own projects. As the day drew to a close, we grabbed our bags and headed to the parking lot.
“I’ll follow you.” I said.
“Okay.” Was her simple reply as she got in her car.
We both pulled out and I followed her to the gym. Turns out I didn’t need to follow her since it was only a few blocks down the road and one turn away.
As we pulled in, I parked and headed to the entrance where she was waiting for me. We went inside and she signed me in as her guest. I nodded to the guy behind the counter looked me over in a slightly judging manner (I guess they all do that?).
Shelly showed me the machines she thought I should work on. I headed to the locker room after she showed me and began to change. I met her as she was coming out from changing. She had put on a black sports bra that pressed her breasts together nicely (never seen her this way), and a pair of running shorts showing off her long legs. That was all she had on.
We headed to the machines she had shown me earlier and we began to work out.
The gym was nice. There were multiples of every machine and she was able to work out right beside me. I won’t lie. I’m not known for going to the gym, so some of the machines were confusing to me and I’m glad she was there to help.
An hour into our workout (How long do people stay at the gym?!), a couple of guys she apparently knew came over and took the machines on either side of us and started working out. I felt really intimidated since these guys were lifting way more than me. I really just wanted to run and hide and pretty much never come back.
However, there is a sense of family in the gym I was unaware of and the guy next to me started to help me out. He showed me how to increase my weights to more than I thought I could lift and before long, I was lifting and doing reps with weights that were a bit more respectable. I didn’t feel so bad anymore.
The guy nearest me was an attractive enough man. He was about 6’1″, trim build. From what I could tell he was fairly muscled but not bulky. He was darker than me, (perhaps Mexican or African lineage somewhere?) and had close cut black hair, but eyes as blue as mine. There was a fairly noticeable bulge in his pants which wasn’t too bad to notice. “Names Ray.” He said as he sat down after adjusting his weights.
His friend, on the other side of Shelly, was attractive, but not as much my type. He was a bit more ‘muscle bound’. He was my height at 5’10” and likely weighed the same, but there wasn’t an ounce of fat on him. He was light skinned, had shaggy brown hair and green brown eyes (honestly, the bulge in his gym shorts distracted me a little) from his eyes. I heard Shelly call him Tim.
As we went through our workouts, I was obviously getting tired. We had been a this nearly two hours. They directed me to the water fountain and I went and refilled my bottle before coming back over, sweat dripping off me.
When I returned, they had all three stood up and were headed to the free weights, talking among themselves. I just followed them over a few steps behind only getting snips of the conversation. They settled in front of the weights and grabbed some and began to do simple curls and flys. I sat my bottle down and followed suite.
“This is our cool down. No need to overdo it.” Tim said.
I nodded and switched to lighter weights and continued with my cool down. 15 minutes later, we were all breathing easier and racked our weights. At this point we were all soaked in sweat and I realized there was no one else in the gym. Holidays? Close to dinner? I don’t know.
“Want to shower before you head home?” Shelly asked me.
“If there is a shower here, I’d love to.”
“Follow us.” Ray said as he grabbed his towel and water bottle heading off to the showers.
I followed grabbing my own things. I also noticed that Shelly was following us too. I figured that the ladies shower was nearby so I didn’t read into it. That was until she followed us into the same shower. There was only one place to shower in the place and they weren’t segregated. (Do ladies not usually shower after a workout?)
Ray, Tim and Shelly were undressing completely normal like, so I did the same. I shed my clothes as well and went to stand under a shower head turning it on. I rinsed and washed trying not to be obvious about looking at the other three.
Ray had a nearly hard cock, about 5″ at present, cut, and shaved smooth. Tim was about 6″ and semi-erect, cut, and had a trimmed bush. Shelly stood there looking at the three of us. Her nipples, light brown, were the size of quarters and she was completely hairless with the most perfect vagina you can imagine. My modest 4″ semi-hard cock stirred slightly and was soon 5″.
I think we all rapidly finished washing as we all soon realized we were looking at each other. We finished and headed one of the saunas, our clothes left in the showers, towels wrapped around us.
Once in the sauna, we all sat beside one another. Shelly was the first to start things. She reached over to Tim and began to rub his leg, his cock growing to an impressive 8″ long, and nearly thick as a can of shave gel.
Ray leaned over “This is normal. If you’re uncomfortable, we won’t hold it against you if you leave man.”
I shook my head. “I’m bi, so I’m okay with this.” I put my hand tentatively on his thigh and looked at him for a read.
He smiled and placed his on mine. I moved my hand up to his balls and began to play with them, our towels since forgotten. He wrapped his hand around my cock as it grew to its full 7″ length (thick enough, pic among my other post).
Shelly and Tim smiled as they saw I was game and she lowered her head to his cock. I stroked Ray’s 6″ cock, realizing her was about as thick as me, as I watched her, my own cock leaking pre-cum.
Ray lowered his head to my cock and I moaned as he swallowed it no problem. Tim smiled at me as our eyes met and I smiled back. He moaned as Shelly cupped his balls.
These blowjobs went on a few minutes before Ray lifted his head and leaned back. I knew what he wanted so I lowered my mouth onto his cock, sliding it between my lips like a pussy before sucking for all I was worth. I’ve been told I give sloppy head…
Shelly stood up and promptly lowered herself onto Tim’s throbbing, glistening member. I watched out of the corner of my eye as it disappeared. I heard loud and clear as she instantly came.
I redoubled my efforts on Ray, but he stopped me. I lifted my head and he motioned for me to sit on his lap. I smiled getting up. I positioned my ass over his cock and slowly, carefully, lowered myself onto his dripping wet cock. In time, I had him in my ass. He placed his hands on my hips and began to bounce me.
Shelly and I matched our bounces as we looked each other in the eyes.
Tim started to stand up, so Shelly got off his lap. He walked over to me and put his cock at my mouth while I rode Ray. I parted my lips and took it. I could taste Shelly and him and I loved it. Shelly watched rubbing her clit in slow circles.
Before long, Ray started to stand, so I lifted off. Tim pulled from my mouth and they switched places bending me over to spitroast me. Tim entered my ass, stretching it more than I have ever been stretched while Ray slid back into my waiting mouth.
The began to time their thrusts with each other, out at the same time and back in at the same time, both bottoming out each time. I was loving it, my cock was dripping pre-cum like there was no tomorrow.
Shelly came over and began to juggle my balls while she rubber her clit under me. I watched her as best I could cause damn she was hot, but I was very focused on the two cocks in each of my holes.
Suddenly, I realized they were both picking up the pace and in short order they were grunting. I was being filled with cum from both ends. I swallowed all of Ray I could (which was most of it). Ray moaned in a slightly higher pitch which was kinda hot. What began to drip, Shelly got under me and caught like it was a game. Tim buried his cock deep in me, grunting loudly, as he shot me full of more cum than I had ever felt in my life.
As they both finished, their softened cocks fell from my holes. Shelly moved to my ass before I could move and sucked the cum out. I have never had this done, but damn! I stood sightly so it would drain more easily for her. When she finished, my shaking legs demanded I sit, so I did.
No sooner had I sat down than Shelly was on my lap, my cock in her. She was facing me and I began to suck on her nipples. This seemed to drive her wild and she rode as hard as she could.
After the pleasure I had just received, I didn’t last. Luckily for her (and me because I would have felt bad), she came hard right as I began to explode into her cunt. We both moaned and screamed out together in ecstasy, our bodies shaking.
As we began to come down from our high, I realized we were wearing cum. I turned in time to see Tim spray one last bit and I caught it on my face as Shelly caught Ray’s on hers. We looked at each other and began to kiss and clean the other off as best we could, my softened cock falling from her now fully loaded pussy.
After a few minutes, we all got our things and went back out to the showers and cleaned off quickly one last time.
“Don’t worry. I’m on the pill and we all are clean. We get tested once a month, middle of the month.”
“Now I know why you asked me if I ever got tested.” I laughed feeling like an idiot as we finished rinsing the sex and cum from our bodies.
We wrapped towels around us and went to the respective locker rooms and got dressed. As we headed out, we hugged each other.
“You said this is normal?” I asked Ray
He nodded.
“How much is membership?” I laughed realizing I could be in good shape, AND get lots of sex.
We all laughed. “I’ll give you the details at work.” Shelly smiled as we began to leave. “Now, we all need to go eat and sleep.” She kissed my cheek as she reached her car, waving to the other guys as they headed to their cars. “See you tomorrow at work.” She put her finger to her lip in the shush motion.
I nodded. “See you tomorrow.” And with that I headed to my car.
Fucking my sisters (BBW) friend in the mountains – MILF
I live in Colorado. Last year during the ski season, my sister and her family came out from the east coast. They rented a cabin in a mountain resort and I came along. It was a big cabin, two floors. Two bedrooms on the first and three on the second floor. My sister told me her friend from college who also lives in Colorado would be coming up for a few nights.
I get to the cabin and i am greeted by my sister and her husband, we bullshit for awhile and they show me my room. As they are showing me my room on the first floor, my sisters friend arrives. (I have never met my sister friend and I had no idea what to expect) The women who walks in is this very curvy blond hair chick. The best way I can describe her ( sorry if it’s not PC) is that she was a BBW. She was def close to 200lbs, she took off her coat and she had these huge tits that were stretching the shirt she was wearing.
I have never been with a girl this big and she kind of turned me on. We all get pretty drunk that night and the next day we plan on going skiing. I can’t get the thought of my sisters friends tits out of my head, and before bed i rub one out.
The next morning, my sister tells me that her friend won’t be hitting the slopes with us bc she is too hungover. So I go out with my sister and her family. After about 5 hours of some great runs, i part ways with my sister and her fam and head back to the cabin.
When I get to the cabin, my sister friend is on the couch wearing yoga pants and a tight shirt with no bra. Her tits are massive, they are literally like hanging watermelons, Her shirt isn’t long enough, and her belly is poking out. For some reason that really turns me on. We talk, I ask her how she is feeling, and she says she feels fine, and she says she sorry she missed out but that skiing is not really her thing. I go shower and I’m feeling horny so of course i jerk off in the shower. I get out I throw on the sweats, and I go and join her on the couch.
We bullshit for awhile, I start flirting with her, just trying to feel her out. The whole time I’m just staring at her massive tits, I’m pretty sure she noticed bc she would position her self and kind of push her chest out every chance she gets.I’m starting to get real hard, and I’m pretty sure she notices. I keep catching her taking quick peeks.
Before I have a chance to make a move my sister and her fam come through the door…. We all have dinner followed by more drinks. Me we all get pretty drunk. My sister, her husband and the kids all go to bed. me and my sister friend go down to the first floor to keep drinking. We sit back down on the couch, and as soon as we sit down she takes her fleece off, her giant tits pretty much fallout, the shirt looks stretched to the max and the bottom of shirt had rolled up, exposing more of her belly. I start pushing the envelope with the question, I think it’s the wine talking, but I ask her the size of her boobs, she replies with a laugh and says she wears a 38gg bra but she thinks there getting bigger bc the bra is starting to hurt her, hence the reason she is not wearing a bra.. I tell her, that I think her breast are amazing, she laughs and ask if I want to touch them and I put both my hands underneath them and lift them and I feel there weight, they fell incredible, so heavy and squishy. By this time I’m rock hard, and she comments on my massive erection with a laugh. She leans in and we start making out, while this is going on my hand is switching from groping her tits and rubbing her belly, while I’m doing this she is stroking my cock, after about 15 mins I move my hand to her pussy, I can feel that her yoga pants are soaked and i start rubbing and kissing her neck. She whispers in my ear to take my cock out..
I stand up in front of her and i tell her to pull my pants down. My cock springs out, and she has a concerned, surprised look on her face, she can’t believe how thick my cock is, she says how heavy it feels, and asks me how thick it is. I tell her and she slowly starts sucking. Gradually shoving more and more down her throat till she gets about 3/4 of the way down and she pulls away with a caught and a gasp. She continues this for awhile, she keeps trying to depth roar it with no luck, and she comments about how she has never had this problem before. she then looks up at me and tells me she wants my fat cock in her.
We go back to her room and she tells me to lay on the bed, I lay on the bed and I start rubbing my fat cock using her sloppy spit as lube, she starts undressing, I have never seen a women of her size naked and I have to say she looked sexy. Her massive tits and her huge belly, complemented by her thick ass. She climbs on top of me and I feel her weight, her massive tits are smothering me. She slides down my chest and continues to suck me off. I stand up and I tell her to lay on the bed, I lift her legs up in the air and I start slowly start filling her pussy with my fat hard cock. She tells me to go slow and I can feel her pussy getting wet. After a few mins I am able to get my cock all the way in.. I start pounding her hard, her huge tits and belly are bouncing all over the place, she’s moaning, and soon I can feel my load coming on, and I tell her that I’m gonna cum, she tells me to blow it on her stomach. I whip it out and instantly unload 3 massive shots on her belly. He laughs and complements my load.
She left the next day, we exchanged numbers and we have met a few times after that, it kind of fizzled out but we still talk every once a while.
( if anyone wants to see pics of my fat cock, or here more about this beautiful women with the huge tits, just send me a pm)
Sunrise surprise – MILF
The week between finals and graduation, a bunch of us poor college students pooled our work-study cash and rented a beach house for a week. It was technically the off-season still, so it didn’t cost us arms and legs. The house had five luxurious bedrooms, gorgeous Atlantic views, and a hot tub. We decided we would invite a shit-ton of people who didn’t pay and basically had a week-long bacchanalia.
Lots of firsts for me on that trip. My first public nudity showed my friends just how big my penis is (7 inches and girthy, nothing special). I mixed alcohol and weed for the first time and wandered at high speed through the house onto the beach like I was in the computer game Quake 3. I turned down my first threesome invitation from her because he wasn’t into it and I knew they’d get married someday, and I didn’t want to be a source of pain in their future. And I witnessed friends fucking for the first time.
The night of the declined threesome, I [22M] shared the master suite bed with three other students: Hoopes[21M], Janey[22F], and Syd[19F]. Now Syd had a long-standing thing for me that I was completely oblivious to at the time–but that’s another story. So the morning after, I woke early to regular movement of the mattress, slow but rhythmic. I was groggy and a bit hungover, so it took a while for me to understand who was rocking the bed. Hoopes was kneeling on the bed, stripped naked to the waist, his long, lean body silhouetted by the rising sun shining through the balcony glass door. Beneath Hoopes lay Janey, on her stomach, whispering “fuck me” as Hoopes gently pulled up her satiny aqua camisole to splay her 36DDs against the sheets.
I screwed my eyes shut and turned back slowly. They didn’t notice me. The rolling of the mattress, like the pounding Atlantic surf, continued without pause. I couldn’t resist. I turned slowly back and opened my eyes just as Janey moaned.
Hoopes was now naked and slowly but powerfully thrusting his cock into Janey’s ample behind. Janey was on all fours, back arched down, head against the pillow, face turned toward me–but with her eyes closed, thankfully. I was completely shocked–my friends didn’t do this!–but couldn’t help but notice that in the quiet heat of their lust Janey had roughly pushed her matching satin aqua panties aside to admit Hoopes’s veiny prick.
I stared, transfixed by this frankly stunning combination of bestial coupling and all-too-human stealth. Hoopes was concentrating on Janey’s body, his rhythm, and staying quiet–he paid no attention to the pasty awakened nerd on the other side of the bed. Janey had her eyes shut and pushed her balled-up fist against her mouth in an effort to stifle her moans of pleasure. Syd slept undisturbed.
My friends rocked together, rocking us all on the bed, faster, faster, then slower but deeper; harder, harder, then gentler, as Hoopes moved his hands from Janey’s ass to play with her nipples. Then faster, faster, harder, harder, deeper, deeper–and Janey must have come, because she lost control of her fist and her mouth, and Hoopes definitely came, all over Janey’s creamy white back, threads of semen glistening in the sunrise.
Janey opened her eyes slowly, sated, and registered my polite, already apologetic face immediately. She smiled slightly and winked, and whispered to Hoopes that they should shower now. I closed my eyes again and feigned sleep as the mattress expanded and raised, relieved of the weight of the morning’s activities. The ensuite bathroom door clicked shut behind me, and I opened my eyes again–to find an awake Syd looking back at me with a horrified, naughty gleam in her eyes, and a grin on her lips.
Thanks to FuntimeR4R for the original prompt and the go-ahead to post here!
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After Thirty years I finally fucked my High school crush – MILF
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.
He decides to finger me while my mom is in the other room – MILF
So I had been dating this guy for a few days and he came over to visit. We were sitting in my mother’s dining room and all of the sudden he’s got me pressed up against the wall, his hand sliding down the front of my skirt and his fingers just brushing against my clit. He goes to kiss me, his fingers just plunging into my already soaking wet pussy and he kept his lips against mine to cover my moans up. Meanwhile we can hear my mother moving stuff around in the kitchen that’s right next door to the room we’re in. He just keeps this up for a minute or two, knowing my mom is coming back in and just sits back down as soon as my mom comes back in like he hadn’t done anything and I’m standing there beat red.
The Not So Silent Night – MILF
Olivette and I had been together on and off for 3 years. This was our first Christmas as a couple, and I wanted to make it count.
She had convinced her parents to let her stay at my house on Christmas night, and my parents had decided to go to a holiday party two hours away. I paid a friends older brother to get a bottle of champagne for us, and wore the silky black dress that she loved to lift from my shoulders.
We hadn’t seen each other in 3 days, but in the mind of two teenage girls it might as well have been three years. Seeing her knock on my door was a gift in and of itself. I flung myself into her arms, knocking presents all over the bricks of my front porch and kissed her cheeks, forehead, chin, and finally: lips. We lingered in the december evening air, perfectly at peace with the warmth of one another.
Eventually we collected the gifts she had brought, and brought them into the living room of my parents home. After pouring ourselves 2 glasses of champagne we opened presents. After 9 years I have a hard time remembering the vast majority of what I got her, or what she got me, but I remember the way her eyes lit up when she said “This is so thoughtful!” and the fires of mischief that blazed in those eyes when she gave me the last present for that holiday season.
As far as I could tell, it was a box filled with odds and ends. There were candles, a feather cat toy, fuzzy hand cuffs, a red bustier and matching thong, and a riding crop. I laughed when I opened it “What’s all this?” I asked “Oh, I’ll show you. Try the red thing on!” I smiled again “help me out of this dress and I will.”
she put a hand on either side of my hips, and pressed the silk against my body, lifting it slowly, and looking into my eyes. When the dress was off she leaned down to my breasts and kissed them tenderly. I ran my fingers through her long blonde hair and exhaled contentedly. She stepped back and nodded towards the currious box which was meant to be my gift.
I stepped into the thong, and fumbled with the clasps of the bustier, “how do I look?” I asked bashfully “good enough to eat” she said with a Cheshire cat grin.
My parents living room had 2 upright support beams separating the family room and dining room, Olivette had the brilliant idea to cuff my hands behind my back, and use those beams as an anchor. Knowing that my parents would be gone for hours, I agreed to be naughty this Christmas night.
Strange as it may seem, the very sound of hand cuffs tightening is enough to send chills down my spine and ruin whatever underwear I have on for the rest of the evening. Olivette knew this, And after she had tightened the hand cuffs she stepped back to light the candles she had brought.
It was strange for her to create an ambiance, but I wasn’t going to complain. She picked up the cat toy, and asked “do you know what this is for?” I rolled my eyes “Of course I do.” she stepped towards me “sure about that?” her left hand cupped my cheek as she pressed her lips to mine. She then spun the feathers against my ankle, and slowly ran them up my leg.
When she passed my knee to tickle my inner thigh I inhaled sharply and began to shake “It’s a french tickler. I knew you’d like it.” I was shocked by how wet she had made me in such a short time. She went to the candle, and brought it to me. Butterflies were in my stomach, and she quenched my anxiety with white candle wax, and a mischievous smirk. I cried out. “More?” she asked with an eyebrow cocked “yes.” I said, panting with desire.
She lifted the champagne glass to my lips “good girl.” I drank deeply. The riding crop came out, and licked my belly. I yelped, and tensed with every lash, but cried for more whenever she stopped.
Once the thong was visibly wet in the candle light, she removed it and forced two fingers inside me. She kissed my neck, and ran the french tickler up and down my spine. “Cum for me, baby.” she whispered. The flood gates opened. I screamed, squirted and went weak at the knees.
She uncuffed me, and kissed my forehead “That was good, baby. You’ll be able to take more next time.” Fucking Olivette was like being struck by lightning, then wanting go out and do it again. But, out of respect for my parents: we cleaned ourselves up, and hid the box in my bedroom closet.
We finished off the bottle of champagne before my parents came home, and I assumed we were home free. Two days later, my dad looks at me and says “I don’t know what you and your freaky little friend are doing when you have sleep overs, but if I find wax on the carpet again, you’re both fucked.” All I could do was laugh.