First Time MilkingbyKessler©
I had not seen Linds in a while. She stopped by with her friend Joan. I had never seen Joan before. She was beautiful, long brown hair and long slender shapely legs to match. They both wore short skirts that hugged their figure. They stopped by to pay a visit and check up on me. I quickly found out the real reason for their visit. They wanted to know if they could have a party at my place and to invite a few friends from college and the local area. I really did not have a problem with that but played like I did. And of course Linds knew just how to sway me over to her way of thinking.
Linds got that look in her eyes that I know so well, and Joan smiled wickedly at me and turned to Linds saying, "Well, I guess we will have to convince him somehow."
Linds giggled, "Hmmm, it has been a while since I had him between my feet and toes. Maybe that would work." I looked at her feet. She wore pumps and her high arches looked so inviting.
I laughed, "Ladies, that would definitely put me in the right frame of mind."
They both laughed and Linds said, "To the bedroom then!" We made our way up the stairs making sure I positioned myself behind them. Joan was directly in front of me and I had a great vantage point of her tight ass and shapely calves.
Joan looked over her shoulder at me and smiled.
Linds commented, "Joan, you have to try that milking thing out on Mr. C."
We made our way into my bedroom and Linds said, "Only if he wants to."
I sat on the bed removing my clothes and asked them, "What is this milking thing you two are talking about?"
Linds said, "It is something Joan has been doing with her boyfriend. I will let her explain it to you."
I had gotten over feeling uncomfortable in the nude in Linds presence. However, being naked in front of Joan, whom I just met, made me feel a bit uneasy.
I stretched out on the bed and Joan smiled saying, "Mmmmm, Linds you were right, for a 40 year old man he does not have a bad looking body."
This put me more at ease with her. I watched as they both slipped off their shoes. Joan's feet looked amazing. Linds was wearing pumps and Joan had on a pair of black mules.
Linds sat on the bed cross-legged next to my right hip. She pulled her long hair back over her shoulders and then grabbed my already hard cock and began to fondle it.
Linds approached the foot of the bed saying to me, "Make room for me and spread your legs please."
I did as she instructed and watched as she took a seat on the bed between my legs. She also sat crossed-legged. Her legs were amazingly long and shapely. Her calves were smooth and nicely formed. She lifted each of my legs up and rested them on top of her crossed thighs. With my legs raised atop her thighs she was able to scoot in closer to me between them. Linds continued to stroke my shaft causing me to moan. She leaned over me, her beautiful face hovering over mine smiling as she said, "I love the way you feel in my hands."
Joan said, "Let me." And reached over grabbing my cock. Linds released me and leaned over to the bedside stand and pulled out the bottle of baby oil from the drawer. She applied a generous amount over my cock and Joan's stroking hand. Joan's fingers were slender and much longer than Linds and wrapped completely around my throbbing shaft.
As Linds applied a liberal amount of oil Joan smiled saying, "That's better, I like the slippery feel and smacking sound a cock makes in my hand."
After a few more strokes she stopped stroking my shaft and began to rub her long thumb very slowly up and down along the sensitive glands at the head of my cock. She finished each slow torturous thumb rub by squeezing the head of my cock firmly. Her doing this to me caused my body to tense up and raise my hips into the air. She saw what her thumb rubbing was doing to me and smiled. Linds saw this and reached in with her left hand grabbing the shaft of my cock between her fingers and stroked it while Joan continued to relentlessly rub and squeeze my sensitive head.
Linds said, "He likes it when you do that with your thumb."
Joan replied, "I can see that. His body is really tense."
I moaned each time Joan's thumb passed over my cock's swollen head. She was relentless as was Linds who continued to pump my shaft. It did not take long before I started to ooze precum. I watched as it leaked out of my slit and on to Joan's thumb.
Joan giggled saying, "There it is. Amazing what my thumb can do."
Linds said, "His cock is throbbing in my hand."
Joan said, "That's a good sign."
Linds and Joan stopped what they were doing and Joan began to fondle my balls as she explained to me about how she wanted to milk me. She explained that she would insert her finger up my ass pumping it against my prostrate. All the while keeping me hard. She said it would allow me to remain hard much longer and my orgasm would be much more intense and longer.
After explaining all this to me I was pretty sure it was not for me. I said, "I do not like anything stuck up my ass. I prefer to remain a virgin there."
Linds laughed, "Oh c'mon just try it once. I will keep playing with your cock while she does it."
Joan said, "It will not hurt you. I have done this many times to Ron, my boyfriend, and he says it is so intense. I know what I am doing and I promise to be gentle."
They both continued to talk to me about it trying to convince me. Joan kept playing with my balls. I watched as her slender fingers worked their magic. Finally after much deliberation I agreed. I further explained that the moment I said stop they would have to stop. They agreed.
Joan slid my legs off of hers and got up from the bed. She made her way over to where she had placed her purse and brought back with her a small jar of KY jelly. I commented, "Do you always carry that with you."
She smiled at me saying, "I never leave home without it."
She assumed her position between my legs, only this time scooted herself in even closer causing my hips to spread even wider and my buttocks to tilt up higher towards her.
Linds looked on and asked Joan what should she do?
Joan told her to get me to the point of precum again while she does her thing.
Linds immediately placed her foot in my lap and inserted my cock in between her big toe and second toe. She began to jerk my cock the length of my shaft all the way up to the head where she paused and gently wiggled her toes back and forth a few times then stroked me again. It was driving me crazy and she knew it. I fit very tightly between her toes.
Joan said, "I can tell u have done this before." She poked her finger in the jar and pulled out a healthy dollop of KY.
Linds said, "It shouldn't take too long before he starts oozing. I just have to work his head between my toes."
Her toes were working me over good. I began moving my hips up and down and my moans of pleasure were coming more frequently.
Linds raised up her other leg and laid it across my lower abdomen pressing it against the shaft of my cock propping it upright. The sight and weight of her smooth shapely calf across my abdomen excited me further.
Joan reach down between my butt cheeks and I felt her gently separate them she lowered her face down a bit to get a better view. She smiled at me and said, "Nice virgin bud you have there. Now you have to relax and let my finger slide in. Do not tighten it up. I promise it won't hurt."
I felt her apply the lube against my rectum and then she gently entered her finger up to the first digit. I could not help but tighten my muscles. She smiled at me and said, "Relax now, I am going to move it around a bit so you get use to my finger." Linds continued to stroke me between her toes as I felt Joan's finger moving up down and around inside me. After a while I felt her finger enter me further. I asked, "Is that it?"
Joan laughed, "Oh no. Only half way, I still got more to go sweetie. I can feel your muscles contracting around my finger. You have to relax and accept me." Then she smiled at me and said, "I love pumping my fingers inside a virgin. At this moment you probably feel a sensation of being violated. That's okay, the feeling of being violated is normal, don't worry after a while the feeling will go away. You and I are going to be real close." Her smile broadened even wider as she pushed her finger in even further.
I said, "I am trying to relax but God u have long fingers!"
They both laughed and Joan said, "That's funny…Ron tells me the same thing." She then added, "I am going to move it around again so you get use to it."
I began to breath harder and Linds asked, "How you doing sweetie? Does it feel okay?"
All I could do was grunt and take short breaths.
I tried to take my mind off of what Joan was doing to me as I concentrated on Lind's golden toes working over my cock. I could not help but move my hips up and down. She applied more oil to her toes and reached down with a free hand to stroke my shaft while her toes began to squeeze and work harder on the sensitive area of my head.
Joan concentrated on what she was doing to me as I felt her finger move even further inside me. She said, "almost there now."
I gasped, "Thank goodness."
Linds commented on how my cock was throbbing and twitching.
Joan said, "That's good he is responding to what I am doing to him."
Linds said excitedly, "There it is, he is starting to precum now."
I looked at Linds toes and saw beads of my precum ooze out of my slit and onto her beautiful toes.
Suddenly I felt Joan's finger slip in further and press against what had to be my prostrate. I arched my back up and groaned loudly, "Oh God!"
Joan said, "That's it I am all the way in now. See how he responded Linds?" Linds laughed, "Hell yes! He bucked so high my knee almost rammed into my chin."
Joan bent her head down further to examine what she was doing to me saying, " I just poked something inside him never touched before."
Linds said, " That's so wonderful."
I relaxed a bit then Joan moved the tip of her finger back and forth against my prostrate. she called it my squirt button. Each time she touched it I felt a tingle race down my legs and into my toes. I also felt a tingle at the head of my cock.
Joan said, "Now we start to milk him Linds. Stop stroking him for a while. Keep him between your toes. I am going to pump his squirt button."
Linds kept my cock locked between her toes. Joan began to slowly pump her finger in and out of my rectum, each time ensuring she made contact with my so called squirt button. She was right about me feeling violated. Yet it felt amazing. I remained hard as I felt her finger move in and out of me. Each time her finger hit my button I felt it in my cock. Suddenly she created a new sensation as I felt her enter me with two fingers. She increased the speed of her thrusts and before long I saw my cum oozing out of my slit. At first I thought it was precum but there was too much of it and it flowed freely. The sensation was strange, as I had no prior feeling of it coming. The flow was beyond my control. Each time she made contact with my prostrate more would flow out in a steady stream. I could not help but moan as I watched it flow onto Lind's perfect toes and foot.
Linds was beside herself as she looked on in awe, "Oh my God he is leaking like crazy look at it, all over my foot! It feels so hot. I love it!"
Joan laughed, "I know. It's great. All I have to do is keep hitting his button."
Joan reached in with her free hand and lifted my heavy balls up fondling them as she increased the pace of her fingers inside me. After several minutes my tense muscles began to tire and I began to let myself go. I became more relaxed as Joan's relentless pounding continued. I could feel the knuckles of her remaining fingers push against my ass cheeks each time she shoved her fingers inside me. Joan recognized the state of relaxation I was feeling and looked up at me smiling, "That's better now, just relax and let us milk you dry." She told Linds to start jerking me again while she tries something new.
Joan removed her fingers from me and repositioned herself saying, "So you like toes and feet eh, well I am gonna finish milking you with my toes."
Linds said, " You go girl, give him those long sweet toes, that's what he wants. "
I watched as Joan remained seated between my legs and pulled her knees up to her chest. She then reached back down spreading my cheeks with her hands. I felt one of her big toes enter my rectum slowly and smoothly. All the way in and then I felt it hit my squirt button just as her finger had done before.
She said, "Oh yes he is very receptive, good and loose now."
My God! It felt amazing as she began to rub the tip of her toe against my prostrate up and down and around. Seeing her long beautiful legs between my legs and feeling her toe pressing against my insides excited me to no end. I rose up onto my elbows, my body shaking with sexual bliss. Linds looked at me and giggled as she continued to squeeze the head of my cock between her toes and stroke my shaft with her fingers. All the while Linds continued to flex her foot as her toe rubbed and pressed my button.
I was shaking with excitement, delirious and on the edge as I watched a slow steady stream of cum ooze out onto Lind's foot every time Joan's slender ankle flexed, moving her toe inside me. I watched the muscles in Linds calf move each time her ankle flexed. I could not help but moan each time I saw this and felt her toe press inside me.
Each time, my body shook uncontrollably when Lind's toe rubbed my sensitive head and Joan's toe hit my button.
Linds said, "Wow! I have never seen him like this. He is losing it Joan." Linds reached over and ran her hand gently along the side of my flushed face.
Joan said, "I know. That's what I like about milking a guy. It gives me complete control."
I gasped through my excitement. "Amazing! Your legs are so beautiful Joan." I leaned forward and tried to touch them but I could not.
Joan laughed and said, "Why thank you." She then raised her right leg and gently placed her calf across the top of my cock and began to rub it back and forth. My cum was flowing continuously as I watched it ooze onto her shapely calf. Her toe continued to work my rectum and Linds slid her toes down my shaft stroking it faster.
Joan smiled wickedly at me and commented, "That's nice isn't it?"
I fell back onto the bed closing my eyes as I felt myself being swallowed by these leggy vixens.
Seeing me do this they both laughed as they continued to work me over with their hands, toes, and legs.
Linds said, "I think all this stimulation is almost more than he can stand. He does not know if he is cumming or going."
Joan giggled, "You don't know how true a statement that is. Right now his brain is telling him one thing but his body is doing something else."
The sensation caused by Joan's toe was incredible and prevented me from a complete orgasm. I continued to ooze my juices for several minutes. I could not control it. My level of excitement was controlled by the pressure of Joan's toe and Lind's feet and toes on my throbbing cock.
It was a strange sensation in that I was being held back from an exploding orgasm. At the same time the urge was not as strong. Joan had a lot to do with that, as she seemed to know just the right amount of pressure to apply with her toe.
After what seemed like an eternity Joan finally said, "Lets make him explode now."
Linds smiled hungrily and said, "Yes. Lets." Then she asked me, "Are you ready to explode?"
My senses were a wreck as I breathed heavily. My heart was racing and my blood felt like fire burning in my veins. I responded through heated breath, "Yes…yes."
Joan and Linds laughed seeing how I was struggling beneath them.
Joan said, "Okay. I am going to start pumping him and you work your magic Linds."
Linds raised her left leg that was resting across my abdomen and locked the base of my shaft between the big toe and second toe. She kept the head of my cock locked between the same toes of her right foot and preceded to jerk me with her feet. Joan tucked her right leg back into her chest and inserted her other big toe into my hole. When she did this I came out of my skin shouting, "No! no! Not both of them!"
Joan leaned forward placing both her hands on my hips saying, "Sssshhhhhh, just relax and let it go," as she consoled me I felt her slowly push her other toe deeper inside me saying, "almost there sweetie."
I squirmed watching her as she looked down between my legs intensely. All the while feeling her toe slip further in along side the other one. Once I felt the tips of her remaining digits push against the outside of my rectum I knew her toe was fully inserted. She looked up and smiled at me and wrapped her arms around the front of her long tucked legs and resting her chin on top of her knees said, "There that's not so bad now is it? Both my toes are inside all the way." I felt her wiggle them up and down inside me as she giggled. This caused me to thrust my hips up involuntarily as I released a long groan saying, "Oh my God."
Linds continued to pump my hard throbbing shaft and leaned over to look at Joan's feet saying , "Oh my God, that looks awesome! I definitely want to try that."
Joan said, "Here we go." She started to slowly pump her toes in and out of me while Linds quickened her jerks on my cock. I matched their pumping and jerking as best I could with thrusts of my own. Each time I felt Joan's toes enter me and press against my squirt button I could not help but grunt. Linds matched Joan's pumping toes with her jerking of my shaft. After a while we reached a good rhythm. Both girls realized this as well and Linds said, "Now we got it going good."
Joan looked over at Linds saying, "Yep, it won't be long now."
Joan said, "He is really loose down here now. He is getting use to my toes."
She began to pump her toes in and out much faster and harder. She unwrapped her arms from around her legs and grabbed my balls with both sets of her fingers and began to fondle them by gently squeezing them and pulling on them. She cupped my swollen balls from underneath with her left hand lifting them up and slowly ran the tips of her fingernails of her right hand across the taught skin sending more shivers through my body. The sensation of her nail tips rubbing back and forth across my nuts sack was a totally new sensation to me. The muscle tone in her legs looked amazing as she flexed her ankles and pumped her toes in and out of my hole. All the while the smile never left her petite pretty face as she concentrated on what she was doing to me. Feeling her fingers fondling my balls and watching her long legs while she smiled at me from above her knees was driving me crazy. My cock was twitching like never before between both sets of Linds toes as she began to concentrate most of her efforts on the swollen head of my cock. Seeing and feeling all this I could not help but raise up in the seated position almost shouting out, "Oh God, oh God!", in unison to Linds strokes and Joan's pumping toes. Their efforts felt so strong as my limp body was totally given to them. I could feel my body being physically rocked back and forth along the bed. They were pounding me pretty hard. Joan's legs were powerful as she was thrusting her toes into me. I was amazed at the strength I felt coming from her long legs and the seemingly tireless effort they exuded. Through prior experience I knew the same was true about Lind's legs. She studied dance and could go on for hours if need be. I knew I would not last long. Eventually it would all come out in the end...right between Linds magnificently tanned toes.
Just as I was beginning to feel the desire to finally cum I felt Joan lift my nuts up between her groping fingers. She then pressed the tips of her toes harder than she had done before against my Squirt button and gently pinched it between them, gripping it firmly with her toes she began to lightly tug and push back and forth on it.