Women in My Life Ch. 03
Author's note: Based on reader feedback and requests, I decided to write a series of stories that are based on women that I have had sex with in the course of my lifetime. This period would normally cover my high school senior year 1959 and the years in the Marine Corps (1959-1963) up to the current day. I will not cover every encounter since by my count I have had sex with almost 50 different women starting back in 1959. I will select my best encounters and I will write about them randomly rather than in chronological order. I will not include any of my bi-sexual experiences when I let men suck my cock or when I fucked them in the ass.
These encounters will include anal sex, oral sex, vaginal sex and infidelity. There is also some bi-sexuality between women and some group sex. If this is not to your liking then I recommend that you not read the stories. This is a period when people slept around and condoms were rarely used. People began to cool it around the mid-1980s when the threat of AIDS became serious. Guys that slept around were called studs and unfortunately if girls slept around they were called sluts. I never agreed with that because I felt a girl had every right to have an occasional roll in the hay as any guy did.
A few of my stories about certain women are already on the Literotica site and I will touch briefly on those encounters. I will begin with 1970 since many of my encounters, in high school, the Marine Corps and my life between 1963 and 1970, I used in writing other stories already posted on Literotica. Each chapter will be named for a girl or group of girls and it will be based, and I emphasize the word based, on real experiences but the names will be changed and the sexual encounters will be embellished for readership. Some of my previous stories that are on the Literotica site are based on some actual experiences, these include; Capri an Isle of Love; An Affair to Remember, Thanks for the Memories and MILF and Did. I know that many readers do not believe authors when they speak about writing of their experiences but I will leave that interpretation up to the individual reader. Others who read this may call me a womanizer or male chauvinist pig. What ever you think while reading the stories the fact is that is the way it was at that time at least in the circle of people that I hung out with. We had sex, we had fun and no one got hurt. I hope that you enjoy this work for literotica. As always all characters are 18 years old and older.
INTRODUCTION
In this chapter you will meet another corporate groupie Sharon. Also you will meet Shirley from my tennis club and Sherry a girl I met skiing in Aspen. Toni is another girl I also met in Aspen while skiing with my best friend Ken. Toni actually traveled to Aspen at Ken's invitation.
SHARON
Sharon was married but recently she was hanging around the Oasis and joining the parties without her husband. She was a pretty girl who got a little too heavy in the hips but other than that she had a nice body with great tits. It was a party at Susan's place that Sharon and I got together very impromptu. As the night wore on and people left the party, there were only a few of us left. Susan was going to drive her pilot boyfriend home so she left Sharon and me together with a few others. The other people left leaving Sharon and I alone and I was surprised that she stayed as long as she did.
I moved over to the couch and sat next to Sharon and looked into her eyes. She really had bedroom eyes and a wanton look about her. I took her into my arms to kiss her and she absolutely melted under my touch. She drove her tongue deep into my mouth as we embraced. I knew she was ready to fuck so I moved quickly. In less than a minute I had Sharon's blouse and bra off and her big tits filled my hands. I rubbed her tits and twirled her nipples as she crooned under my touch. I dropped my head to her tits and sucked on them as I unfastened her slacks. Sharon lay back on the couch as I pulled her slacks down her hips.
She was beet red with embarrassment when she spoke, "Oh my thunder thighs!"
I ignored her embarrassment and pulled her slacks off her body. Then I pulled her panties off and moved in between her legs. Sharon almost leaped off the couch when my tongue touched her quim. She grabbed my head and pulled it into her pussy. I ate Sharon to a series of orgasms before I removed even one article of clothing. I then stood up and stripped off my own clothes and I followed Sharon's eyes to my cock. I was rock hard and it was standing straight out from my body.
"I heard that you were hung," Sharon whispered as she sat up on the couch.
She took my cock in her hand and played with it briefly before she covered it with her mouth. Sharon then moved her mouth over my balls and licked and sucked them before kissing her way up my shaft. Looking up into my eyes, she slid her lips over my bulging head with her hand still wrapped around my shaft. Her tongue swirled under the ridge of my crown as she sucked me deeper into her mouth. She tested her gag line and was soon taking my entire cock down her throat.
My cock was alive and my hot flesh pulsed against her lips. She pulled me deeper into her mouth, pressing her lips tightly against me and sucking hard. The feel of my hard cock sliding between her lips and over her tongue had me on the verge of a huge orgasm. Sharon had slipped her hand into her cunt and fingered her dripping pussy. The smell of sex was rampant in Susan's apartment.
I grabbed the back of her head and started fucking her face. She was slurping and sucking as fast as she could. Sharon drooled as she tried to keep up with my thrusting motions. Her fingers dug into my thighs, moving her head as I pumped my cock in and out of her mouth. I knew her pussy needed attention but I wasn't about to stop anything she was doing. I could sense that I was going to cum soon and I warned her but she just kept sucking me in anticipation of receiving a creamy treat.
I felt my cock swell and knew that she was about to receive my load. Muffled moans escaped from her throat as she eagerly sucked my dick awaiting her prize. She moved her lips up and down over my shaft in rhythm with my thrusting motions. She was drooling like crazy and I could feel it running down my pecker onto my balls. My breathing became more erratic and I was about to lose control. Sharon looked up at me with those big eyes and nodded her head, letting me know she wanted to taste my seed and then she covered my cock with her mouth just as I lost it. I let out a soft grunt as I pumped stream after stream of hot cream into her mouth.
I shot the first jet against the roof of her mouth then several more blasts of hot cum poured into her mouth. She moved her hand under my scrotum to squeeze out the last few drops and then Sharon had another orgasm. Apparently the feel of my throbbing cock in her mouth, the taste of my seed and her hand in her cunt was just too much. The pressure in her lower tummy gushed out through her pussy and soaked her fingers.
My cock fell from her lips and cum dripped from her lips and chin as her body jerked and shuddered in orgasm. Sharon looked up at me when she was done, blotches of cum glistened on her lips. The smell of pussy in the room was powerful. I took Sharon's hand and licked her fingers clean. Then I led her by the hand to Susan's guest bedroom.
Sharon got in the bed and lay back as I took in her beauty. For a slightly heavy woman she was in great shape. She had nice legs, a narrow waist, great abs and nice big firm tits. I looked at her pubes and noticed the light brown tuft of hair above her pussy.
I walked over to the bed and sat on the side of it. I stroked Sharon's shapely legs and luscious thighs. My hand drifted up to her mound and I felt that she was still wet with desire. She smiled at me as I fingered her pussy and licked my fingers clean of her juices. Then she opened her arms and welcomed me into her body for the first time. I slipped between her thighs and slid my hard cock into her quim. Sharon uttered an audible gasp as I hit bottom. I began to fuck her slowly and eased my cock almost all the way out of her pussy before plunging it back in. She was lost in the lust of the moment.
"Oh that's it fuck me, fuck me slow, fuck me good, fuck me forever," she whispered.
Just hearing her asking me to fuck her was an incredible turn-on for me and I picked up my pace. Sharon threw her hips up at me as if to try and get me deeper in her cunt. I felt my orgasm approaching but I didn't want to cum before she did so I tried to slow down.
"No, no don't stop, fuck me faster, I'm so close," Sharon begged.
I picked up the pace again as we both raced toward our orgasms. I don't know who came first this time because we were so close but Sharon wrapped her legs around me and humped me for all she was worth as I spurted my seed deep in her womb. We continued to fuck each other until we were drained. I collapsed on top of Sharon and she didn't seem to mind my weight as she held me and cried out.
"Oh thank you, thank you," she said over and over.
I rolled off of Sharon and lay next to her on the bed. She smiled at me and then snuggled in closer. We talked for the next several minutes and she told me that she was happy that we got together. As I lay next to her I caressed her breasts, neck and arms, teasing her skin with my fingernails and tongue. Sharon made a low, drawn out sound. Deciding that I'd teased her enough I started on her naked breasts. As I sucked her warm flesh into my mouth and rolled a nipple between my teeth, Sharon let out a moan of pleasure.
Sharon then moved down the bed, gently took hold of my cock and took me into her mouth, rolling my cock around and getting it wet with her saliva, while her hand worked my shaft up and down at the same time. Seconds later, she straddled me. Her hand wrapped around my now slippery cock and I felt the tickle of her pubic hair just before her soft flesh nudged my helmet and then it was suddenly engulfed by the heat and tightness of her pussy.
Sharon grabbed hold of the top of the head board on either side of my head as I held onto her hips. She rocked her hips back and forth, pressing downwards and working the walls of her pussy as I slid into her further. The next motion of her hips caused her to gasp in pleasure as my full length penetrated her. She began to work up and down, back and forth as she moaned in pleasure. She felt particularly tight in this position and the unhurried pace felt sensuous and wonderful. Sharon continued to ride me at a slow, even pace as I relaxed and let her take charge. As she fucked herself on me I could hear the smacking and sucking sound of her pussy as my cock moved around inside her.
Her firm medium sized breasts jiggled as Sharon picked up the pace. She pushed her hips down until our groins met and then lifted up until just the swollen tip of my cock remained inside her. She seemed to know just how far to move so that my cock never slipped out of her pussy. Her thigh muscles felt firm and tight under my hands as she worked her body on me. The speed of our groins slapping together increased as we fucked faster and harder. We really had our rhythm going now and I thrust up into her as she lowered herself on me. Her pussy contracted around my cock as her eyes fluttered and she emitted a high pitch scream. Sharon grabbed onto my shoulders as she rode out her orgasm. I ejaculated into her again flooding her cunt with spunk as she collapsed on top of me.
Sharon covered my face with kisses and then plunged her tongue into my mouth. As she kissed me she murmured softly into my neck and shoulders. She thanked me over and over as she held herself tightly to me.
"Are you going stay here tonight?" I asked.
"No I have to get home and I do want to leave before Susan returns," Sharon replied.
"I think we have time before Susan gets home," I said as I imagined Susan impaled on her boyfriend's cock.
"Let's grab a shower and then leave," Sharon suggested.
We both showered together and I loved washing her big firm tits but we didn't fuck again that night as Sharon was serious about getting home. After the shower we dressed and then left Susan's apartment. That was the only time that Sharon and I got together. It was completely unplanned but we had great sex together. Sharon made her way through other guys in the office before she settled in on one guy. Sharon started spending a lot of time with John who she eventually married after her husband divorced her. John and Sharon then moved to New England when John took a job there.
SHIRLEY
I met Shirley at our tennis club. She was a pretty blonde divorcee who was dating the former club manager Steve. He had taken a job with a competitive club but Shirley remained a member at our club since she had more girlfriends there. She stood about 5'6" and I guessed weighed no more than 110 pounds. She kept her hair short just covering her ears and she had beautiful blue eyes. Shirley was small breasted actually almost flat chested but she had shapely legs and a curvy ass.
Shirley asked me if I would play mixed doubles with her in the upcoming club tournament. I agreed and we decided on practice times and scheduled some matches. On day we were playing at noon time against another couple. Our opponent Bob was an asshole as he was always hitting hard shots at Shirley. Shirley held her own but one time Bob hit an overhead right at her and the ball hit her in the lip after it bounced in front of her.
Shirley's lip was cut but not badly. Still a trickle of blood ran out. I told the other couple that we were done playing and actually our court time was due to expire anyway. The other couple left and then Shirley and I walked off the court. I stopped her once we were behind the backdrop and checked her lip again.
"Is it bad?" she asked.
"No it's not. It's just a small cut and the bleeding has stopped. It's not even noticeable," I said putting her at ease.
Then I teased her and said, "I should probably kiss it to make it better."
I leaned in and kissed her lightly. Her lips were so tender and when I looked into her sexy blue eyes I just had to kiss her for real. I kissed her again surprising her but she relaxed and kissed me back. Then I took her in my arms and held her to me and we kissed and my tongue sought out her mouth. I felt Shirley trembles in my arms and I felt that I just had to have her. I broke the kiss and dropped to my knees. I ran my hands along her shapely legs up under her tennis skirt and I cupped her firm shapely ass. I stared right at her panty covered pussy and ran my hand over her vulva.
Walt please stop you shouldn't do that," she gasped but I continued rubbing her bare thighs and panty covered pussy.
Shirley was breathing hard and she seemed confused when she spoke again, "Please stop before this goes any further."
I pushed Shirley's tennis skirt up to her hips and leaned in to kiss her creamy thighs. She gasped aloud at the touch of my lips to her naked skin. I knew that she was struggling with the decision on how far she should let this go. I could smell the sweet aroma of sex that was given off by her pussy as my face moved closer to her crotch. I kissed her inner thighs just below her panties. She groaned with pleasure as she reached down with her hands to control my head. Shirley tried to keep my head from reaching her pussy but I moved the panties to one side of her vulva baring her sopping wet cunt. I tickled her outer lips with my fingers and then let them slip inside her vagina.
Shirley was so wet that two of my fingers slid in easily and she unconsciously relaxed her grip on my head. I moved my mouth toward her and closed over her pussy shoving my tongue into her wetness. Shirley cried out and grabbed my head again but this time she held it tight to her quim. I lapped at her pussy as I fingered her with two fingers. Then I spread her pussy lips apart and located her throbbing clit peeking out from its protective hood. Shirley was really excited. I sucked on her hard clit and she bucked her hips into my face. I reached around her and cupped her shapely ass cheeks in my hands as I drove into her pussy with my tongue and nibbled on her clit.
"Oh sweet Jesus, I'm cumming. Hold me, please hold tight," she screamed as she lost it.
The climax rocked her body and I held on for dear life as she thrashed, twisted and bucked almost losing her balance. I kept right on eating her pussy and I held onto her shapely ass as she thrashed about. Shirley slowly calmed after her intense orgasm and I continued to lick her until her pussy was dry as she ran her hands through my hair.
"Oh that was something I really came hard. Thank you, thank you!" she murmured.
I stood up and Shirley adjusted her panties and tennis skirt. Her eyes traveled to my crotch and she spotted my cock straining to get out of my tennis shorts. I smiled at her and then we both walked upstairs to the main level. Shirley was blushing as if everyone at the club knew that she had just had her pussy eaten.
I told Shirley to ride with me and we would get some lunch although my plan was to fuck her before we ate. I had already made up my mind to blow the rest of the work day off. I pulled into a motel parking lot and got a room as Shirley sat in the car. I drove around to where the room was and then I leaned over and kissed Shirley again. I reached under her tennis skirt and pulled her panties down and played with her pussy. As I fingered her cunt I removed the panties from her legs. Then I sat up and said it was time to go inside.
"Give me my panties back," she demanded weakly.
"Nope, I'm keeping these for now," I replied.
I got out of the car and opened the motel room door. Shirley got out of the car and held her tennis skirt down tight as she dashed for the room. I chuckled at her predicament. Once in the room Shirley jumped on the bed but she held her skirt down over her pussy. I dropped my tennis shorts and briefs to my knees and got on the bed with her. I lifted her skirt and gently pried her legs apart. Then I moved between her thighs and placed my cock at the entrance to her cunt. She shivered in anticipation. I eased her back down on the bed and proceeded to feed my thick cock to her.
"Oh we mustn't, we shouldn't, it is not right, I'm dating Steve and then oh yes, oh it feels so good, oh, oh, fuck me, yes fuck", she cried.
I slid in and out of her pussy slowly allowing her to adjust to my size and continued to go deeper with each thrust until I was buried balls deep in her pussy.
"Oh my I have never been so full of cock, fuck me, make me cum, make it last forever", she cried out.
I pounded her pussy making sure that my cock was in constant contact with her clit. Shirley had multiple orgasms as I fucked her. I pulled her tennis top out of her skirt and pushed it up over her sport bra. Then I pushed the bra up over her tits. She had very small pretty firm tits with rock hard nipples. I twirled the nipples in my fingers and then leaned over taking one then the other in my mouth.
She went wild telling me. "Oh yes, suck my tits, suck my nipples, fuck me good!"
I could feel my balls start to tighten and I knew it wouldn't be long before I filled her pussy with my cum. Shirley stiffened and then had another violent orgasm.
She yelled, "Hold me, please hold me, I'm cummmming!"
I reached around behind her and pulled her toward me as she shook and trembled throughout her intense orgasm. As she was cumming so did I and I fired a barrage of cum into her pussy. As she started to recover I laid her back down on the sofa and slowly fucked her as my cock softened. My cock was swimming in her cunt; there was so much jizm in there mingling with her own juices.
"Are you okay, Shirley?" I asked her.
She smiled at me and said, "My God, I have never cum like that in my life, nor have I ever had anyone cum that much in me before."
She looked down at my soft cock and took it in her hand, "You are big," she said as she stroked my cock to hardness again.
"Let's take our clothes off," I suggested.
Shirley smiled at me and replied, "Yes, let's do that. We should have done that earlier.
We stripped off our clothes and Shirley got in bed on her back. She held her arms open to me welcoming me between her legs again. I crawled between her legs and slipped my hard cock back in her pussy. I never wanted this to end and I wanted to fuck this hot woman all day. I fucked Shirley as long as I could before I shot my second load of the afternoon. She had multiple orgasms and the final one was so violent she nearly bucked me off her body.
Then she collapsed and cried out. "Please stop, I have to rest. I have never been fucked so thoroughly in my life. I want this to go on forever but I need a rest. I am not sure I can cum any more."
"Are you up for a shower?" I asked.
"Absolutely," she replied.
We both showered together and as I soaped her body Shirley leaned back against me and I reached around and fondled her tits lovingly. She cooed as she was in ecstasy and totally relaxed. I also spent a lot of time washing her curvy ass and her hot pussy. I startled Shirley when I slipped a very soapy finger into her asshole. I knew that I caught her off guard so I didn't pursue her ass any further at that time. After the shower we dried each other off with the motel towels and as she was drying me, my cock was at full attention.
"Does that thing ever go down?" she asked as she dried it tenderly.
"Not as long as I am around you", I said cupping her ass and then asked, "How about if I give you a massage?"
Shirley smiled as I retrieved the lotion. She crawled back on her bed and lay face down. I admired her shapely ass and I wondered if she would let me fuck her there. I wanted to save her ass for later though so I told her to turn over on her back.
"Front first," I said as I rolled her over.
I started at her feet and worked my way her legs and thighs but I did not touch her pussy. Then I moved my hands up to tits and twirled her delicious nubs in my fingers. I worked my hands back down her torso and this time I touched her pussy and fingered her gently as well. I located her clit again and rolled it in my oily fingers emitting a short gasp from her. Shirley seemed to have another small orgasm just from being touched.
"Time to do the other side," I told her as I rolled her onto her stomach.
I marveled at her soft flawless skin and shapely ass. This time I started with her shoulders and worked my way down to her ass, thighs and legs. She was so relaxed I felt that she might fall asleep. I paid special attention to her ass and placed a well-oiled finger in her bunghole. My finger was so slick and she was so relaxed that it slid in easily. I continued to massage her shapely beautiful ass and finger her hole. I added a second finger and although it was much snugger Shirley didn't complain. I pulled her up by her hips until her curvy ass was in the air and she lay with her head to one side on the bed. She was almost crooning as I continued to finger her asshole and then began to finger her pussy as well.
I removed my fingers and eased my engorged cock into her pussy. I began to fuck her slowly and then added first one then two fingers back in her asshole. Shirley was on the verge on an uncontrollable orgasm and as she began to thrust and shake, I took advantage of her state and tried to slide my cock from her cunt to her asshole. I managed to get the head outside the sphincter and then Shirley panicked. As she bucked and shuddered with an intense orgasm she almost impaled her ass on my cock. Only when she started to come back to earth did she realize that my cock was about to enter her ass.
I had no intention of hurting Shirley but as I stared at her perfect ass I had to caution myself not to rush it. I was about to fuck my dream ass and I didn't want to do anything to screw it up. I applied lots of lotion and then saliva to my cock as I prepared for my fantasy fuck to come true. I got on the bed behind Shirley and lifted her almost lifeless body up so that her ass was in the air. She kept her head on the mattress and she had a distant dreamy expression on her face as if she was in a different world.
I slid my cock into Shirley's well lubed asshole. Although she had been loosened up by my fingers, my cock was stretching her to new dimensions. Shirley shook her head no, but no words came out of her mouth. She was like a rag doll in my hands and I steadily pushed my cock into her until it was buried in her ass. I fucked her slowly at first and then I really picked up the pace. I pounded her ass and my hips slapped against her ass causing her incredible ass cheeks to jiggle. Shirley just moaned and grunted with every thrust of my body. She was incapable of another orgasm so I was just using her for my pleasure. I added another ass fuck to my collection and this was the finest ever.
I gave her one final thrust then I stiffened and shot my wad into Shirley's asshole. I moved my hips slowly as my cock softened somewhat and I watched as cum trickled out of Shirley's ass. Finally my cock softened slightly and slipped out of Shirley's ass with an audible popping sound as more cum ran out of her ass and down over her cunt lips.
We rested for quite awhile and then I decided to take her ass one more time. I grabbed Shirley by the hips and pulled her lifeless body back up until she was on all fours. I pushed a thick finger into her asshole and tested her tightness then I added a second finger which caused Shirley to gasp. I worked the two fingers in and out of her ass stretching her as much as I could. I then placed my big erect cock back between Shirley's beautiful smooth round ass cheeks and pushed into her asshole.
As I entered her a second time Shirley pleaded, "It hurts, it hurts, please don't."
But I was not to be denied this beautiful ass and I was resolved to take her again. Shirley tried to move away from me and ended up on the bed lying flat on her stomach. I followed her to the prone position and lay on top of her shapely body with my huge cock between her ass cheeks and in her asshole. I began to hump Shirley at a slow pace and then faster with my hips pumping into her. Shirley's screams and moans were louder than ever as her lithe body took my big cock. Shirley started taking my cock better this time and unconsciously massaged it with her amazing ass muscles. I lifted her back to her knees on all fours and reached around to feel her tits. Her nipples were rock hard as I twirled them in my fingers. I then moved one hand down to play with her pussy and Shirley went wild humping her hips faster and faster. Then I placed both hands on her hips and watched my cock penetrate her curvy ass as she moved her hips in time with my humps.
Shirley yelled for all to hear, "Oh my God, fuck me, fuck me, please fuck me!"
I complied with her demands and pounded her ass as hard as I could. Shirley squeezed her ass cheeks together as she orgasmed and I joined her and shot a huge load of cum deep into her ass. Shirley screamed and moaned as she felt me pump several shots of cum into her rectum. Shirley's beautiful body radiated heat as I pumped cum into her ass. Shirley was almost out of breath but started to return to normal breathing as I caressed her body lovingly. I eased my cock from her ass and traces of cum ran out of her asshole between her cheeks and over her pussy.
I learned later that I had taken Shirley's anal virginity and I was thrilled that she had given it up to me. Shirley and I continued to play mixed doubles matches and afterward we headed to our favorite motel for incredible sex. I still remember that first day that we had sex and the exciting things we did that day. Although Shirley didn't suck my cock that day she proved to be an excellent cock sucker and one day she actually sucked me off at the tennis club behind the back drop. We took some risks at the club which added to our excitement. I would eat her pussy and she would suck my cock. Once we even fucked there as Shirley wrapped her legs around my waist as I held her by her shapely ass. We did pretty well in the tournament finishing in third place. After the tournament Steve put the pressure on Shirley to join the other club so we stopped seeing each other. But she is one of the women I always thought of even later in life.
SHERRY
My best friend Ken and I went skiing for a week every year in Colorado. This one year we went to Aspen and stayed in a condo near Snowmass. Ken would always invite some girl that he had fucked before to join him on the trip. This year a woman named Toni showed up the second day that we were there. Toni was nice enough even though she seemed a little shy. I assumed she was slightly embarrassed that I was in the other bedroom while Ken was banging her at night.
Toni was a decent skier and she didn't hold us back. The three of us enjoyed our day on the slopes and our Après Ski. One day we stopped at one bar in Snowmass and there was a rally good band there. That's when I met Sherry. She was standing alone near the bar when I asked her to dance. She smiled and accepted and we hit the dance floor and stayed out for five songs.
"I really need to rest a minute," Sherry told me after the fifth song.
"Sure, would you like to join us?" I asked pointing to the table we were sitting.
Sherry accepted the invitation and joined Ken, Toni and I at the table. Introductions were made and we enjoyed the rest of the afternoon together. Sherry was staying at Snowmass for two days and then heading up to Vail to see some friends there. Sherry was a strawberry blonde with a solid figure. She was about 5'6" and I guessed about 150 -- 160 pounds. She was solid as a rock and had big tits. Her hips and thighs were full but you could tell she was in shape.
The three of us closed the Après Ski bar and then agreed to ski together tomorrow. Sherry said goodnight to us and that she would see us tomorrow. Ken, Toni and I went to dinner and then returned to our condo. It didn't take long for Ken and Toni to go to their bedroom and then I decided to watch TV in my bedroom.
The next day the four of us skied together and had a great time. Sherry was a very accomplished skier and was probably the best of the four of us. After skiing the four of us showered dressed and went to dinner in Aspen. Following dinner we found a place to dance and party and we had a good time although there was something funny about Toni that day. I sensed that Toni was jealous of Sherry being a better skier and dancer. It's funny how women can get that way at times.
The four of us went back to our condo where Sherry had left her car. I invited Sherry in and I spotted the look of disdain on Toni's face. Sherry accepted and came in for a nightcap. Toni seemed uncomfortable with Sherry in the room so she said goodnight and went into the bedroom. Ken followed her shortly leaving Sherry and me together. We sat on the sofa together with our feet up on the coffee table looking at the fire. It was a romantic setting and Sherry cuddled up to me. I put my arm around her and soon we were kissing and petting. I started to take of her sweater but she stopped me.
"Can we go into your bedroom? She whispered.
I nodded and whispered, "Yes."
We walked into the bedroom and I closed the door. I turned on the small light in the room so that we could see. The room was dimly lit but we could see each other very well.
"I want us to undress each other and I want to undress you first," she whispered.
Sherry walked over to me and then she pulled my shirt up and off my body. I stood up as she dropped to her knees in front of me to lower my pants and underwear but first she removed my shoes and socks. Sherry then took hold of the underwear waistband and slowly pulled them down my legs. By this time I had an erection and it sprung out at her as she lowered my briefs. My cock dangled in front of her face as she removed my briefs from me one leg at a time. I stood completely naked in front of her with my cock just inches from her face.
Sherry took my cock in her mouth and sucked it gently. She licked all around it and ran her tongue up and down the shaft. Sherry was a very accomplished cocksucker and I knew that I would soon blow my load. She sucked me deep into her mouth and swirled her tongue around the shaft of my cock. I felt my orgasm building and I warned her that I was going to cum.
"I am going to cum soon Sherry," I cautioned.
She took her mouth of my cock and looked up at me with those deep brown eyes and replied, "I want you to cum in my mouth I want to taste your cum Walt."
Sherry returned her mouth to my cock and resumed sucking it until I exploded in her mouth. She continued to suck my cock and swallow every drop until my cock was drained dry.
"Oh Walt I love your cum. It is so tasty and so much of it," Sherry sighed as she licked her lips.
Sherry then stood up still fully clothed and lifted her face up to me to be kissed. I kissed her and held her in my arms and then I began to undress her. I dropped to my knees, unbuckled her belt and unfastened her jeans. I pulled the jeans down her legs stopping to remove her shoes and anklets. Then I pulled her jeans all the way down and off her shapely legs. I then took hold of her panties and slowly peeled them down and off her legs. Sherry was trembling slightly and had goose bumps on her skin. I held her panties up to my nose and inhaled the smell of her femininity. Sherry gasped at the action. I reached behind Sherry and grasped her firm shapely ass in both my hands and pulled her toward me. She gasped again as I kissed her loins and fondled her ass cheeks. I could smell her sweet sex but I held off on licking her pussy.
I stood back up and I lifted Sherry's sweater up and removed it from her body. Then I reached behind her and unhooked her bra. I was beginning to harden again and my semi-erect cock brushed against her thighs. I slid the bra straps slowly down her arms baring her large firm breasts. Her nipples were rock hard and I couldn't resist tweaking them a little which caused Sherry to moan softly. I then turned her around so that her back was to me and I reached around and cupped her firm tits in my hands. I played with her tits and nipples as I kissed the back of her neck. My cock was now fully erect again and it brushed against her buttocks as I fondled her.
I started a slow gradual descent down the back of her body kissing her neck, shoulders and back until I knelt behind her. When I reached her buttocks I planted kisses on both ass cheeks and tickled her crack with my tongue. Sherry couldn't take anymore of my teasing so she turned her body toward me, grasped my head in both hands and pulled me against her pubes. I found her pussy with my tongue and I grabbed both of her ass cheeks as I began to lick her pussy. Sherry gasped aloud as my tongue found her clit and she held my head tightly as she experienced a mild orgasm. Her body shook and she seemed to hold onto me for balance.
"Oh Walt I need to lay down. Can we go to your bed?" she said breathlessly.
I guided Sherry over to the bed and she immediately splayed her legs and welcomed me back to her pussy. I burrowed my tongue as deep into her as I could and then I just sort of licked and sucked my way up. When I got to her clit I used the very tip of my tongue to tickle it. I flicked my tongue over it once and then used the tip to explore the folds of flesh on either side of it. Sherry was now moaning and she arched herself so that her clit stuck out even further like a little cock. I licked it once more before I took it between my teeth and gently nibbled it.
Sherry went wild and started bucking and moaning loudly. She pulled my head to her pussy as she cried out in ecstasy. I sucked her clit as deep in my mouth as I could and Sherry humped my face for all she was worth. I was pleased that I was able to get her that excited and I sucked harder and played with her wonderful clit with my lips, tongue and teeth. I don't know exactly how many times Sherry came but she finally begged me to stop as she collapsed on the bed, her body in spasms.
I was not done with her however so I eased my dick into her pussy and began to fuck her slowly. Soon my cock was sliding easily in and out of her and we picked up the pace. Sherry wrapped her arms around my back and her legs around the back of my legs. She arched her back as she humped me hard and fast and I made sure that my cock stayed in contact with her clit as I plowed her cunt. We fucked hard and long working ourselves toward an exhaustive state. I could feel my orgasm building but I did not want to cum before Sherry and I was relieved when I felt her tense up.
"Walt, hold me, hold me, I'm coming, oh, oh, oh" Sherry said louder than she wanted as she reached her crescendo!
She tensed up wrapping her arms around my back and her legs around the back of my legs in a vice like grip. I held her trembling body tight and I could feel her drench my cock with her pussy juice just before my own intense orgasm. I could feel it building in my balls and then I exploded filling her with my man seed. It seemed endless as I fired round after round of hot cum into her pussy.
I remained still with my cock still in Sherry's pussy as she uttered unintelligent moans and sounds and her body quivered. Her vagina muscles were involuntarily squeezing and releasing my cock, milking all the juice out of it. My deflated cock slipped from her vagina and she flinched as cool air touched her opening.
"Oh that was incredible. You are a very good lover, Walt," she sighed.
"Well you are too and I really enjoy making love to you," I replied.
"I need to rest for awhile, my body aches so," she said softly.
We rested for awhile and at this point I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass. I moved her to all fours with her ass elevated and she placed her head on the mattress turned to one side so she could see me. I started playing with her pussy and her curvy ass lubricating her asshole with her own cunt juice. Then I grabbed the lotion that I had brought with me and put an ample amount in her asshole. Sherry moaned and cooed as I fingered her pussy and her asshole simultaneously. I tired to get her asshole slick enough so that I could fuck her ass.
When Sherry didn't reject my probing I realized that she was going to let me fuck her in the ass. I put an ample of amount of lotion in her asshole coating the tiny puckered opening of her anus and lubricating the rim. I added my saliva to my lotion covered cock and nestled my dick against the entrance of her rectum momentarily before easing it inside her ass. I always found that body lotion and saliva will make my cock as slippery as possible. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Sherry moaned as my penis filled her hole.
"Go slowly at first," she said sexily and then added, "And not too deep at first and then deeper."
I fucked her with long and deliberate strokes until my cock was sliding easily back and forth in her ass. I caressed her shapely buttocks as I watched my penis move in and out of her rectum worming around inside of her curvy ass. For some reason I looked at the wall and I saw a reflection in the mirror on the wall. It was Toni. She had opened my bedroom door far enough to see and she was watching me fuck Sherry in the ass. I don't know how long Toni had been watching us but I didn't care as I returned my attention to Toni.
I caressed her big tits and tweaked her nipples as I leaned over her body and said loud enough for Toni to hear, "Sherry you have a hot ass, I love fucking you in your hot ass."
My hands freely roamed her body and I pulled her hips drawing her backwards impaling her on my inflated member. I reached for her pussy to finger fuck her and diddle her clit but I found Sherry's hand already buried in her cunt. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Sherry felt the warm fluid being squirted inside her anus and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking her cunt as her anal muscles squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. Sherry writhed around and her body arched off the bed as a climax of massive proportion tore through her loins.
My cock slipped from her ass with an audible pop and I flopped down on the bed next to her. She surprised me when she covered my cock with her mouth and sucked any remaining cum from my tool. The both of us were exhausted and Sherry curled up in my arms. I looked toward the door and it was closed again. The two of us then dozed off.
When I woke up in the morning Sherry was gone. She left me a note reminding me that she was headed up to Vail and thanked me for a great time together.
TONI
I was the first one up as usual and I made the coffee again. Ken and Toni eventually emerged and we shared the morning coffee. We had breakfast, dressed and headed for the slopes. Toni was a cool toward me that morning but as the day wore on she warmed up. Ken on the other hand was dying to know if I fucked Sherry the night before.
After skiing that day we skipped the Après Ski as the three of us were exhausted. We went back to the condo and had a couple of drinks and then headed for the Jacuzzi. The Jacuzzi was in a small glass enclosed building that was so steamed up you could not see in or out of it. We wore warm-ups over our bathing suits and dashed for the building. Once inside we lost our warm-ups and got in the Jacuzzi. So far we were the only three people in it.
Toni wore a very tasteful two piece bathing suit. It was emerald green that matched her eyes and showed off her red hair. Toni was attractive but not beautiful. Her figure was decent and I guessed her to be about 34-24-35. She was very fit and had great abs and legs. The three of us sat in the hot tub with me facing Toni and Ken as they sat next to each other. We chatted s the warm bubbly water soothed our bodies.
Another couple came in so I slid over next to Toni to make room for them. Ken had his arm around Toni as we talked. Then I felt a hand brush my thigh. I thought it was an accident but then it returned. Toni then started rubbing my crotch under water and searching for my cock. Her hand snaked into my bathing suit and she grasped my hardening cock. She didn't try to jerk me off but it seemed as if she was evaluating my cock. Shortly after I was fully erect she removed her hand from my bathing suit.
We stayed in the Jacuzzi for almost an hour and then decided to head back. As it turned out other people were coming in to use it and it was just as well that we were leaving. We went back to the condo, showered, dressed in tees and shorts and sat around having a drink by the fire. I looked at Toni and it was obvious that she was not wearing a bra under her tee and I doubted if she bothered with panties under her shorts.
"Walt, Toni would like to try two guys at the same time," Ken said,
I froze when I heard his words. I took another sip of my scotch and replied, "Really!"
I looked at Toni and she blushed but nodded the affirmative. I smiled and answered, "I'm available."
Ken and Toni both laughed at my reply. Then Ken said, "Well let's get started."
I followed them into their bedroom and without hesitation the three of us stripped and got naked in bed. Toni lay back on the bed and Ken and I went to work on her. We started sucking on her firm tits as we fondled her ass and fingered her pussy. Ken worked his way down her body and began to eat her pussy. Toni reached for my cock and guided it into her mouth. Ken then slid his cock into Toni's cunt and humped her hard and fast. We were all hot and we all came quickly. Toni took my load down her throat and milked my cock dry as Ken shot his seed into her womb. Toni covered Ken's dick with her womanly juices moaning on my cock as she experienced her first orgasm.
Toni kept sucking my cock keeping me in an erect state until I was ready for more action. I laid her on her back and eased my cock into her pussy. She was tight and I was sure that my cock was touching areas in her womb for the first time. I started with slow movements and then picked up the pace pounding her pussy hard and making sure that my cock stayed in contact with her clit. She opened her mouth as if to scream but Ken was there to fill it with his cock. I then rolled us both over keeping my dick in her as I assumed the bottom position. Ken knew what I had in mind and moved behind her to work on her ass. Ken began to rim her and eat her ass. Toni looked surprised but did not object as Ken stuck his tongue deep in her asshole.
Ken was now applying lotion and fingering Toni's ass as she humped herself on my cock. I just lay there and let Toni fuck herself using my cock for her pleasure. As she screamed with a spasmodic orgasm, she stiffened and then collapsed on my body. Ken had used that opportunity to insert his dick in her ass. As she slowly recovered from her very intense orgasm she realized that Ken and I were still fucking her but that he now had his cock buried in her ass. Ken's cock was a little longer than mine but about half as thick. He had the perfect cock to break in an ass. I learned later that Ken had been trying to ass fuck Toni but she kept putting him off.
Toni told us that she didn't want to do this but it fell on deaf ears as Ken and I pounded both her pussy and ass. It was clearly her first ass fucking. Ken and I were close to cumming and our urgent gyrations were getting to Toni again. Ken was the first to cum and I witnessed the surprised look on Toni's face as she felt cum in her rectum for the first time. Toni and I came at the same time and she shivered and trembled as I blasted my load into her womb. As we calmed down we rolled to our sides with our dicks still in her and as we relaxed our cocks softened and slipped from her pussy and asshole.
Toni lay there in a confused state with cum seeping from both her pussy and ass. Ken and I stroked her body and played with her tits and stiff nipples. I started to get aroused again as I fondled her cute tits. I thought about her ass and I decided that I really wanted to fuck her in the ass too. I moved to my knees and rolled Toni over on her stomach. I lifted her by the hips and slipped my semi-hard cock into her pussy. Toni was so drained she just went with the flow and let it happen. I slowly fucked her in the doggy style position and my cock eventually hardened again. Ken had moved toward her face and offered her his cock. Toni was hesitant about sucking on the cock that had just been in her ass but Ken was persistent and had his way with her.
I started playing with her ass as I fucked her. I applied a generous amount of lotion and inserted a finger in her asshole. She tensed up at first but then relaxed. Now she was triple penetrated for the first time with Ken's cock in her mouth, mine in her pussy and a finger in her ass. I was anxious to get into her ass.
I pulled my cock from her pussy, lubed it up with lotion and saliva to make it as slick as possible and then put it in her ass. Toni panicked as my cock pushed past her sphincter and she tried to get free but Ken held her by the ears and I held her by her hips. She was shaking her head no as I eased my cock into her going deeper and deeper until I was buried to the hilt.
As I looked down at her marvelous ass I relished the view of my big cock sliding in and out of her bung hole. I really got into it and started to pound her ass as it loosened up and accepted my cock. At that moment I realized that more than anything I wanted to see my dick fucking a smooth tight ass. I love to feel my pubes slam against the impaled buttocks of my bent over partner flattening the fleshy globes as I thrust into the depth of their ass. I love to watch my cock slide through my partner's well stretched anus to disappear into the bowels only to re-appear for a renewed thrust. It is a huge turn-on to ram and slam my cock into a bare and defenseless ass so that my impaled partner is dominated. As I watched my cock penetrate Toni's ass I thought of every girl in this position when I fucked their ass.
I came back to reality as I heard Toni whimpering. Ken had moved his cock down between her tits and was tit fucking her. We were using her for our pleasure and it was obvious that Toni was starting to get into it. I could feel cum moving from my scrotum and I flooded her ass with my seed. Ken was shooting his jizz all over her tits and hitting part of her face in the process. Ken and I collapsed on the bed and Toni plopped down between us. The three of us fell asleep in the king sized bed.
The next morning I woke up with a piss hard-on so I rolled over on top of Toni and fucked her as long as I could. Toni had multiple orgasms as I fucked her. I pulled out of her and went into the bathroom to pee. Just as I vacated her pussy Ken was there to fill the void. I came out of the bathroom and then Ken went in to take his morning piss. Toni looked at my still hard cock and told me to come back to bed. I lay down on the bed and she immediately covered my cock with her mouth. Ken came back out of the bathroom and he got behind her and slid his cock back into her pussy. I came in Toni's mouth and Ken came in her pussy.
Toni was leaving that day so we took the day off from skiing. The three of us spent the morning in bed and Toni again experienced cocks in her pussy, ass and mouth. She had cum in all her holes and she seemed to have adapted to the butt fucking. Ken and I drove her to the airport later and then we took the rest of the day off from skiing. We walked around Aspen and had dinner before returning to the condo.
Ken and I skied for two more days and then we returned home. It was a very memorable ski trip and one with unexpected pleasures. Toni never joined us on future ski trips but Ken always had some woman join him. Toni was the only one I fucked however and the only woman that Ken and I ever shared.
NEXT CHAPTER
Some more Corporate Groupies and some road trips.