The MILF’s Big Surprise
My neighbor is the true definition of a MILF. Her attitude, her stature, her build. She was a real catch for her husband. That’s of course if she likes to fuck as good as she looks. From my past experiences the two rarely meet. A beautiful woman is less likely to be as wild as a plain girl. Something like an overcompensation mechanism. Still she would be worth a good look.
They moved in a few years ago and we get along fine. Her husband looks good and between you and me, I think they make a good looking pair. They had one child, a girl who had graduated high school the next year. But Jean looks great even after having a child. I think Jean said she was a cheerleader and a dancer when she was younger. She loves her body and poses often when we are just talking. She wears tight shorts and tank tops all the time in the summer and she points her ass at you when she bends over to pick something up. Sometimes I think about that ass. I respect her husband and their marriage so I’m kind and polite and treat them like friends. At least that’s what I thought I was projecting. What happened next was a Big Surprise.
I had set up a small bench in the garage to do some repairs and was busy focusing on the work at hand when I noticed Jean standing at the end of the driveway. She was carrying a container and the newspaper. Her legs were crossed in a pose and she rocked a little. She was active when she was young and still has that definition in her legs and waist. I must have stared at her for a long time as she got an impatient look on her face. One I’d never seen before. I motioned her to come up and I put my work tool down.
Her husband was away on a work related trip and her daughter was away at school. My wife works all day while I do contract work. So, the neighborhood was quiet and both our houses were empty. Jean sat the things on the bench and resting her hands on the edge of the bench she crossed her legs again and leaned forward, propping up her shoulders. This was a sexy pose that made it easy for me to see her cleavage. Her hips sort of shoot out to one side and she smiled with a very satisfied expression.
After a moment her hips pushed back against the air. When she pulled herself upright again she looked like she was squeezing her butt muscles together. I looked around the neighborhood cleverly and asked if she could give me a hand with the container and put it by the sink. She looked disappointed and picked up the pile and waited for me to lead. I walked past the bench to the other end of the garage. I was thinking about being so turned on by her actions and wondered what her intentions were. But, how would I know? How could I ask her?
As we move toward the washer and dryer I heard her ask if I could help her with something as well. I turned and looked to see her standing with her legs crossed again. ‘Sure,’ I responded. I didn’t have a reason not to. She held out the newspaper and container and had a sly but pleading look on her face. OMG! Is she hot. If we younger and single, I’d get in such big trouble. I’d be chasing her around and embarrassing myself, ruining our family reputation. I was staring at her with my ‘whatever you need’ smile when she said it, ‘Have you ever done anal before?’
I just froze. My brain was in overdrive imagining how awesome that would be and how wrong this was but I couldn’t interrupt. If that’s what she wants I’ll do it. Yeah she wants it. This is so wrong. I want to give it to her. This could end badly. That’s when she said, ‘I know you like my body. I’ve watched you look at me from across the street.’ Ok, so maybe my projection was a little flawed. I tried to smile. She continued, ‘Do you want to fuck me in the ass?’ My heart skipped and I must have turned white as I stared at her. Her legs were still crossed as she wavered there with a pathetic plea now on her face. I had her permission, but where to take this. My wife was gone for a couple hours. My dick was in charge. What the hell. My expression changed and she smiled. I squinted and with a snide grin said, ‘Show me that ass of yours.’
Her expression melted into a contented smile as she turned and bent over exposing her beautiful, round bubble butt stuffed into her tight shorts. She waved it back and forth in front of me. I wanted to touch it, rub my hands all over it. But, I just stood there and said, ‘What are you waiting for, I said show me.’ She must have loosened her tight shorts when she turned around because when she reached back they just slipped right off her ass and down her legs. That big beautiful ass just shook and jiggled. The thong underpants barely hiding a red butt plug. ‘Well, do you like it now?’ she said in a silky voice. My crotch twitched and I had to adjust myself or risk injury.
I groaned as my dick hardened in my pants. I reached out and placed my hand on her ass with my thumb right on the cup of the butt plug. She shook and moaned. I pressed in and she moaned louder. She was pressing back against the pressure. That’s when I knew we were actually going to have sex and not just sex but anal sex. I used my coolest voice, ‘Don’t embarrass yourself here, let’s go inside so we can have some privacy.’ Then I slapped her ass and opened the door into the house.
As we walked through the door I asked, ‘Do you want me to just fuck and cum in your ass, or do you need me to pound you until you cum?’ She looked back at me over her shoulder with an innocent eye and slack lips. It felt like I was asking her to reveal her darkest secrets. It must have taken her by surprise that I would even ask. Jean seems like the kind of girl who is probably used to just saying ‘go’ and then enjoying the ride. My mind, or dick was thinking of something else.
‘You do want me to fuck your ass, I can see now that you need it. I can help you out. You don’t have to answer right away. Maybe you’d like to suck my cock while you think about it…’
She was still frozen there with those innocent eyes. I pointed to my lump and gave her my best ‘Well, I’m waiting’ look. She shook the innocent expression off her face and focused on the goal at hand. My cock and her mouth. Her hands deftly opened my pants and exposed my stiff handful. A sound escaped her lips as it came into view, ‘I knew you’d be enough,’ she said as she rubbed it. She squatted down and I stopped her, ‘Drop your shorts first and lose the shirt.’ Again Jean got an expression on her face like she was exposed or caught being bad.
Her body was short and firm and she stood up allowing the shorts to drop to the ground exposing her mound covered by the lace thong. She stepped out of them as she swiftly pulled her shirt over her head. Her matching lace bra barely held her perky breasts in place as she jiggled. Her sex mound was smooth and I could make out the crease down the middle. ‘That’s nice,’ I said as she walked back over and grasped my dick. My pants slipped to the ground and she squatted down again to service my cock. Her hand and mouth started to work my man meat cautiously, she was slowing down. Maybe she was having second thoughts. Time to apply a little added incentive. So I asked if she liked having that plug up her ass. She moaned and quietly replied, ‘Yes.’ I continued by saying, ‘How often do you like having a real cock in your ass?’ She shook a little and moaned while licking my rod.
She didn’t answer. I continued, ‘You said mine was enough. Did you mean big enough?’ She squeezed her butt cheeks, arched her back and sucked the tip of my dick into her mouth. Her hand rubbed my shaft so I said, ‘Use your hand to show me how you like play with that butt plug.’ I could feel the shaking of her core. She reached one hand back to touch the plug and her moaning increased. I insisted that she play with it so I could watch. She adjusted my cock in her mouth so she could use both hands to work the butt plug. I put my hand on the back of her head to help steady her. Once both hands were around her ass her attitude started to change.
Her fears must have been abated as she began to moan and groan. Her hips started bouncing as her excitement increased. This also increased her ability to suck cock and with little effort she was working my sausage in and out of her mouth. Now I had her, that’s good. ‘Would you like that big cock in your ass?’ She moaned affirmative. ‘Do you just want a quicky…’ She moaned a little. ‘Or, do you want me to pound my cock into your ass until you cum?’ That did it and she pushed down on my cock as far as she could and held herself there while she frantically moved her hands around the butt plug, pushing, pulling and twisting. I let her snort as she held my cock deep in her mouth while she kept working the butt plug in her ass.
I pulled on her hair and she groaned. I tried to slide my cock out of her mouth as she balanced there. I felt her suck hard to keep my meat in her mouth. She was still playing with the butt plug. I told her, ‘Stand up so I can help you with that toy in your ass.’ Her eyes opened widely and she easily straightened her legs while keeping my dick in her mouth. I have long arms and was easily able to reach her crack and find the thong had dropped around her ankles. The butt plug was slick and hot. I pulled it most of the way out and looked at what kind it was. It was shaped like a short fat dick, bright red with a bulbous head and ribbed. Her mouth pulled free of my meat and she licked and kissed the shaft. When I pushed the plug back in roughly she groaned, wrapped her arms around me and rested her shoulders on my waist.
I pushed and pulled at the plug until it was fucking her ass in a rhythm that kept her breathing hard and wanting more. I did this until the head of my cock was oozing and the tingling had stopped. She was pushing and wiggling as I said, ‘Did you forget about my cock and your mouth?’ She groaned absentmindedly and returned to my meat. When she put it in her mouth the taste of my pre-cum made her moan and again she starting working the entire length in and out of her mouth. I continued to prepare her ass by pounding the mini-dick in and out, spanking her cheeks with my hand. I was ready and I was pretty sure she was ready. So I said, ‘Would you like that dick deep in your ass instead of your mouth?’ Her legs shook and I felt the butt plug push out of her hole.
‘Right here,’ I say, ‘up against the wall. Feet back and spread’m.’ I always wanted to say that. Like a cop arresting a perp. She was already weak and shaky as she turned and stretched up the wall as far as she could like a cat after a nap. She is a little short and I had to squat down to line up my slick cock with her waiting hole. I pushed in and she pushed back. I slid the head in and wiggled it around saying, ‘Is that what you want?’ She moaned loudly, ‘Yeah,’ is all she could say. So I pushed in and watched it slide slowly, relentlessly up her ass channel until her feet were up on her tippy toes. Then she said, ‘Oh yeah!’ I held her up with my dick as her legs began to shake. She began wiggling her ass trying to hump my cock. However, I was deep and firm. Don’t get me wrong, it felt great. I just wanted to send her a message that she would remember. When she needs it, I can deliver.
I pulled back to let her down and she wobbled but tried to keep my dick deep in her ass. I began pumping in and out. Her breathing became rapid and she groaned louder the longer we went. I reached up and rubbed her perky breasts, squeezed her hard nipples and pushed her against the wall, up on her toes again and held her there. Her body was limp and shaking as she collapsed against the wall. I whispered in her ear, ‘You love that dick in your ass don’t you?’ ‘Yes,’ she gasped. I pounded her a few more times not letting her drop from her tippy toes. I instructed her as I pounded, ‘You’re going to cum for my cock aren’t you?’ ‘Yes,’ she gasped again a little more sincere. She’s mine now, ‘You’re going to want me to fuck you in the ass until you cum whenever I want aren’t you?’ Her voice went up, ‘Yes!’
Just then her body stiffened and jumped hard. She screamed and clawed at the wall as I held her up again on her toes. Her ass clinched around my thick shaft as she climaxed. I could hear her pussy juices dripping on the floor. I let her spasm there for a minute until I could tell she was about done. I pounded her ass a few more times as her body began to weaken. No sense in wasting the opportunity. I said, ‘We’re not done yet.’ Jean looked over her shoulder, a look of being worn out mixed with fear So, I continued pounding her ass and lifting her up on her toes until her voice raised again. She quickly came again and moaned loudly, ‘Oh I’m cumming again, oh yeah, oh fuck!’ I punctuated our agreement by saying, ‘I’ll see you tomorrow, same time. Have the butt plug in. Be ready, like today.’
She was breathing hard and her legs were weak as she relented, ‘Yes, whatever you want.’
The next day I was waiting. The garage was open and I was finishing the project on the work bench. The time came and went. I closed up assuming she had second thoughts and wasn’t going to show. It was a chance I had to take. An hour later I was reading in the living room when there was a soft knock at the door. I opened the door and there was Jean with a concerned look on her face looking like she was about to turn around and leave. The obvious signs were her shorts and tank top had been replaced by long jeans and a sweat shirt. I turned on the charming friendly neighbor look, ‘Won’t you come in?’ She walked through the door silently and I directed her to the living room. ‘Please have a seat.’
As she sat down I could see her twitch and settle herself. Maybe she has the butt plug in as instructed. I stood by my chair and gave her my best ‘did I do something wrong’ look. She looked up at me with pleading eyes, clinched her knees together and said, ‘About yesterday. Thank you by the way. But, I can’t keep doing this. Bill’s been away and I needed some help, that’s all.’ I smiled and nodded, ‘No, thank you. Paula and I don’t have sex much anymore, so thank you.’ She looked relieved and squirmed a little. ‘You know that is a fine ass you have there. The smooth skin and the firm roundness. So, hot and moist. It was a pleasure pleasing you. Can I ask you something?’ She squirmed a little and smiled. Let’s see how firm she really is on backing out.
I looked out towards the back yard, ‘Can I show you some of the flowers that have come up?’ I reached out my hand and Jean took it standing up. She squinted slightly and wiggled her ass. Then she took a deep breath and followed me out to the deck. There I pointed out a flower on a low stand. She bent over to smell the fragrance. When she stood up she flinched a little. Interesting, I thought to myself. I pointed out another just across the patio. She headed towards it and I followed watching the way she moved her ass as she walked. I do believe she is wearing the mini-dick. As she bent over to smell that one I heard an obvious moan and her hips shook a little. ‘Let’s sit here for a minute. Can you spare some time?’ The look on her face was melting and she didn’t answer but slowly moved toward the bench.
As Jean sat down on the bench she gasped, wiggled and let out a sigh. Now I’m sure she has the butt plug in and with a little guidance this could still happen. ‘I haven’t had a good fuck like that in a while.’ I said quietly. She blushed a little and smiled. ‘I mean that cute little butt plug… and my dick… I mean, you liked the real thing better than that toy didn’t you. You know what I mean?’ Her face remained red and she dropped her eyes to the ground. She tried to hide the fact that she was slowly grinding her ass onto the bench. I was watching. ‘Oh, take a look at this plant here.’ I said pointing to a mint planted in a large pot. As she got up I could tell she was obviously getting excited and when she adjusted her pants I noticed her reaching back to adjust the mini-dick residing between her cheeks.
The plant was across the patio again and I could see each step was very stimulating for her. I couldn’t wait any longer and when she bent over I placed my hand on her mound with my thumb on the waiting butt plug. ‘Oh! Hey!’ she started to say. I squeezed my hand pushing the butt plug down and lift her pussy lips up. She reached both her hands back to try and stop me. I held firm and squeezed again. Her hips shook. ‘Oh god!’ she exclaimed the fight in her starting to fade. I squeezed again and again. ‘That big cock never did get to cum deep in your ass.’ I said as I continued. She was still holding on to me but was becoming more help than hindrance. ‘Let’s go inside so I can fuck that ass once more. Then we can be done. OK?’ She shook all over at the thought and loosened her grip. Her voice had weakened, ‘Ok’ was all she said. She straightened up and started heading for the house but I kept my hand between her cheeks and rubbed as she wobbled into the living room. She was whining a little as we stopped.
‘You like my big dick in your ass don’t you?’ I pried with my questions as I wiggled the plug and her pussy. A little coercion will help convince her of what we both want. ‘Yes!’ she admitted. I wanted to make sure she was really ready. With a strong arm I applied pressure between her cheeks. ‘Do you want me to fuck this hot ass of yours?’ She gasped as she was lifted to her toes. Her body jerked and shook as I held her there. ‘Oh! Damn you.’ Almost ready, I thought to myself. ‘Tell me you like me pounding your ass until you cum.’ I was still standing behind her as she leaned forward and arching her back looked over her shoulder to say, ‘Just do it.’ I pulled my hand away and slowly sat in my favorite chair. She bounced her ass in the air and the expression on her face turned wanton. With both hands she pulled her cheeks apart through her pants and massaged her crack, ‘Oh fine, I want you to make me cum.’ Now we can get started.
I got up and closed the shades, ‘Take off your clothes. I want to see that clean pussy of yours.’ With her clothes off I could finally see her beautiful pussy. Her lips were peeking out from the crease of her gash which was red like her face. My clothes were off just as quickly, my boner sticking straight out. Her pussy was clean shaven except for a small V shape of curly hairs pointing to her clit. Jean had one hand holding the mini-dick in place and she was wiggling it around and staring at my hard man meat. ‘Let me eat you out first. Lay down on the floor.’ She looked at me with an expression of guilt and astonishment. I handed her a pillow from the couch for her head. Gracefully getting to the ground she pulled her knees up exposing her glistening slit and the butt plug which she continued to work with her hands. I knelt down and blew on her lips which made her gasp. Then with a big tongue I planted my mouth right over her pussy. My tongue slipping smoothly into her hot sweet treasure.
‘Oh yeah!’ she growled as I worked her pussy over with my mouth. Her juicy cunt was twitching and I could feel her clit growing out, poking at my waiting lips. I sucked and licked at it until she shuttered. Then I deftly slid around to offer her my man meat for her hungry mouth. She was breathing hard and I watched her consider what to do. I rubbed it against her partly open lips until she licked it and welcomed it into her mouth. I turned my attention back to her now dripping pussy. A little 69 before we fuck. Planting my mouth over her pussy again I reached my hand back to grab onto the butt-plug. She released it into my capable hands. Now I could work on her pussy and ass at the same time. Jean was really starting to let go and sucked my dick in. I pulled it back out without skipping a beat with her ass and pussy. She sucked at it and bobbed her head on the pillow. Now she’s into it. I thrust my tongue deep in her moist treasure as I worked the plug in her butt. In return she grabbed my waist and pulled my rod deep in her mouth.
It didn’t take long before she came, hard. Jean’s orgasm had her body heaving and she was gagging on my dick. Pulling back a little to let her breath I asked, ‘You like that don’t you?’ She made a deep grunting sound. ‘Now I’m going to fuck this pussy of yours before I pound it in your ass.’ Quickly I spun around and positioned myself for insertion. I was looking straight into her concerned face as she said, ‘No. Wait…’ But it was too late. Her pussy was wet and hot and with one thrust I was balls deep. ‘Oh!’ she gasped. I pumped the full length in and out. She closed her eyes and wrapped her legs around me, holding me in. I pumped, banging our pubic bones together. She started humping against me shouting, ‘Oh fuck… yeah. That’s so good. Don’t stop now. OH!’ Jean was having another orgasm, bigger this time. She went stiff as she shook. About halfway through her orgasm I thrust hard a couple of times and her orgasm started anew. Extra points for multiple orgasms.
After a few minutes of kissing her nipples and slow thrusts I pulled out. ‘I still haven’t cum. Roll over so I can pound that sweet ass of yours until I dump deep up in there.’ Jean is now weak but eager and rolling over pushes the pillow under her hips creating her favorite position to be pounded. The butt plug had fallen out during the pussy pounding and I slid the head into her warm empty hole. ‘Oooh!’ she moans. I can’t help but try to persuade her further, ‘Can you feel my dick in your ass?’ She answers quickly, ‘Yes.’ She twists her hips and squeezes her cheeks. I push in a little further. “Do you want more?’ Her hips hump up and she demands, ‘More!” Again I push in till I’m more than half way in. ‘It’s getting deeper.’ Now she is rocking back pushing herself onto my hard rod saying, ‘Give it to me.’
Now I’m not a mean guy but I can’t help it when a woman wants me to fuck them. ‘Tell me you want my cock to pound your ass.’ Good thing she can’t see the evil grin I have on my face as I say that. Jean is breathing hard, her body still humping at my meat, ‘I want you to pound my ass with your cock.’ That’s better. I slide the rest of the way in until she starts to slide on the floor from the force. ‘So deep.. So good.’ she says dazedly. I slide out and in the full length a couple times. ‘Oh yeah, fuck my ass.’ I pump a little harder. ‘That’s it… Yes!’ She’s moaning with each thrust. I slip my arms under her shoulders and grab on. I pull down and thrust in wedging my dick as deep as I can. Again Jean shakes and stiffens. ‘God, I’m cumming again!’ she says breathless. Another orgasm already. Let’s not stop there.
So, I pull out a little ways and let her spasm. Her breath is ragged and she’s got a light sweat on her skin. ‘Do you want me to cum in your ass?’ All I hear is, ‘Oh god.’ So, I push in all the way again and hold her there. ‘Oh god, yes! Cum in my ass. I want you to cum in my ass!’ That’s what I wanted to hear. I start to thrust in deep and relentlessly. She’s totally committed now and is matching my thrusts with her hips. Her back is arching and she squeezes her ass, milking my stiff rod with each withdrawal. I keep pounding as her breath shortens and I get closer to my own orgasm. ‘Tomorrow, there’s no second thoughts. No excuses. You’re going to come over and get fucked by me. Right?’ Jean knows now what she wants. ‘Yes!’ She’s getting close to another orgasm. I must insist, ‘Yes what?’
Jean rockets into another orgasm and screams, ‘Yes! I will come over tomorrow and get fucked by you, please!’ My cock keeps pounding through her orgasm. ‘Good job. You’re making me cum. Are you ready?’ Her voice is squeaky, almost exhausted, ‘Please, cum in my ass, oh god.’ I pin her down with all my weight and start cumming as deep as I can. Again she starts milking my dick with that beautiful ass. This time I’m sure she will follow through.
The next day there’s a strong knock at my door and there’s Jean wearing her short shorts and a tank top. Her face is red and there’s a look of desire in her eyes.