Carol felt the thick head of my cock between her rounded buttocks and just outside her nether hole. She knew that it was finally about to happen and she felt her stomach turn with the thought of committing such a depraved act. I put an ample amount of lube on my cock and then added my saliva to it making it as slippery as possible. Once I was satisfied that my cock head was slick enough I introduced to the tight ring of Carol's anus. Carol looked back over her shoulder at me as she felt me pushing my cock against that intimate part of her body.
"Please go easy, be gentle," she reminded me.
I slowly pressed against her tight opening and noticed that Carol was holding her breath. I told her to relax and breathe deeply as I continued pressing forward. Carol felt the initial thrill of her sphincter being forced open by my thick cock and her first response was to try and avoid the anal invasion. I held her hips and I continued to push forward past her resisting body. Carol's mouth gaped open and she grasped the bed sheets in both hands as my cock head cleared her sphincter and lodged in her anal channel. Carol unintentionally flinched and caused more of my cock to slide inside. She cried out.
"Are you okay?" I asked.
Carol nodded and then she once again reminded me to go slow. I gave her a few seconds to recover and then pressed forward again and her flower opened up for me. She just needed a few minutes to get used the unfamiliar sensation of being so filled from behind. Carol then responded unexpectedly as she accepted my cock in her ass. So pushed her butt back toward me and then moved forward. She did this for awhile and it seemed as if she were accepting and rejecting my cock at the same time. Finally my cock was buried to the hilt in her ass and we began moving together. I felt my balls slap against her pussy each time I thrust into her hot ass.
"Oh, this is so sexy. It feels so good but I feel dirty at the same time. If my parents could only see their precious daughter now," Carol murmured.
Carol had been raised by very strict parents and she had always been taught that pre-marital sex was taboo and dirty. I too wondered what her parents would say if they could see their daughter with an 8 inch cock in her ass. Carol's lust took over and she rolled her ass in tiny circles as she was consumed with her first anal fuck. I looked down at her firm buttocks and I marveled at the way my thick shaft stretched her nether hole. I tired to imagine Carol's parents, whom I had never met, standing on either side of her watching as her asshole opened and contracted around my cock.
Carol reached between her legs and into her puffy cunt. Her juice was oozing from it and she rubbed her stiff and aroused clit. I picked up the pace and began to fuck Carol's ass with steady full thrusts. She gasped at the new almost unbearable sensation surging through her rectum. There was no pain now but just a glorious feeling of being stuffed with cock. She felt full and a little bloated but the pain had disappeared quickly and the bloated feeling was gone also. Carol loved the taboo feeling of being filled with cock in her ass. The thought of this forbidden act along with her clitoral stimulation pushed Carol closer to yet another climax.
I was trying to hold off my threatening ejaculation as Carol's movements intensified with her pending orgasm. We were both perspiring and I held to Carol's shapely buttocks as I slowed my pace slightly in an effort to slow my eruption. Carol groaned loudly as her head dipped down to look between her legs and she pushed back in an effort to get more of my cock in her.
"Oh Walt, fuck me. Fuck me in my ass, it's so good so wicked, I love it," Carol cried out.
Carol was going wild with my cock in her ass and I had never seen anyone take to anal intercourse with such abandon for their first time. Carol balanced herself on both hands as she thrust backward impaling her ass on my thick cock. I knew that I could not hold out much longer. I reached around with one hand and found Carol's pussy and engorged clit. With the other hand I squeezed the rock hard nipples sticking out from her flat chest. Her clit throbbed as it clamored for attention and her pussy clenched my fingers as it released her warm love juice. The points of her nipples were excited beyond desire and my cock was clamped in her well stuffed bottom.
Carol was out of control as all she knew at this point was that she was being fucked up the ass with a very thick cock and it felt fantastic. She was on the verge of her most intense orgasm ever and she struggled frantically seeking her climax. A few more seconds of rubbing her stiff clit sent Carol into a mind blowing orgasm. Her body stiffened and then spasmed out of control as she moaned loudly and struggled to breathe. The intensity of her climax was too much for me and I grunted as I shot my spunk into her forbidden tunnel. Carol's eyes flew open in surprise as she felt my hot thick semen rush into her rectum and splash off her bowels. Her face was pure ecstasy as she turned to look at me as my cock continued to spurt its sticky fluid up into her.
"Give it to me, cum in my ass, oh I can feel it. it's so good so nasty," Carol cooed as she was overcome with passion
Carol fell forward on the bed as I continued to marvel at the beautiful ass that I had just deflowered. As she lay before me she clenched and unclenched her ass muscles causing cum to ooze out of her asshole. It looked like a small spring as the semen intermittently bubbled up and trickled out of her ass between her ass cheeks and over her puffy pussy lips. I stayed hard and stroked my cock as the last tiny drops landed on her ass. I then realized that I was going to stay hard and I decided to try and fuck her ass again.
I told Carol that I wanted to fuck her ass again and in an almost business like fashion she pushed her self back up on her knees. She turned her head to the side and smiled at me waiting for the second penetration. I pushed my still erect slippery cock into Carol's now gooey asshole. Carol felt her sphincter being stretched again but this time she enjoyed the sensation of her ass being filled with my thick cock. As I pushed inside her my spunk from the previous ejaculation was squelched almost obscenely with my cock. My previous deposit squeezed out around my shaft and oozed from Carol's asshole running down between her buttocks and plopping on the bed sheets.
Carol was an extremely hot woman and her fucking technique was incredible. I stayed crouched behind her and placed my hands back on her hips as I fed my long thick cock deep into Carol's accommodating back passage for a second time. Carol pushed her hips back at me and her bodies slapped loudly together.
"Yes, yes, oh I love it. Fuck my ass with your hot cock," Carol yelled to me and then she cried out, "Make me cum again fuck my ass with that big cock."
As before Carol lowered her head to the bed and turned it to the side as she grasped the bed sheets. But this time she grabbed the sheet in the thrones of passion and not because of apprehension. I could feel her taut muscles massaging my shaft in her ass as I held on to her slim waist and I caressed her curvy firm ass cheeks. Her sphincter grabbed the base of my cock as she worked her lithe athletic body. Carol was an incredible sex partner who had just turned into a fantastic ass fuck. I knew that I was getting close to losing it again as Carol manipulated my pecker with her undulations and muscles and that I would soon be adding more semen to join my previous load in her ass.
Carol had her hand back on her clit and rubbed herself frantically as she had another violent orgasm thrashing and panting wildly. I felt my seed travel along my scrotum and then spurt into the recesses of her ass. Carol felt the second ejaculation shoot into her bottom and she wallowed in the feeling of the warm liquid once again soothing her ravaged ass. Carol squeezed her ass muscles extracting every drop of cum from my cock until I went soft and slipped from her hot gooey ass with an audible pop. Carol collapsed face down on the bed and savored the moment. She knew now that she was hooked on anal sex and that she could expect to be ass fucked regularly from now on. I flopped next to her and held her to me as we kissed and rested.
"I never thought that I could get so turned on from anal sex. It was incredible I felt like I would never stop cumming. The feeling of your hot semen shooting into my ass was unbelievable. I never expected it to feel so good just from being so full," Carol murmured as we lay together.
"I am so glad that you liked it as you know I loved fucking your ass," I replied.
Carol then cuddled back up to me and we dozed in each other's arms. Later we had vaginal sex as Carol rode my cock until she came and collapsed on me as I shot another wad in her pussy this time. For the next two years Carol and I had a very steamy relationship.
Carol brought sex into the office but only when we were by ourselves. She would lock the office suite door and then come into my office and lock my door. Carol would then pretend to show me something important and she would come around to my side of the desk and lean slightly forward. Carol always wore mini skirts that showed off her shapely legs and blouses or sweaters that ended at her narrow waist. I slid my hand up her leg and I felt her tremble slightly as we had played this game before and she knew where it was going. I let my hand ride about and down her stocking covered leg for a few minutes. Then I let my hand wander above her knee and past the top of her elastic top hose. Carol shivered as my hand touched the bare skin of her thigh. I caressed both of her thighs and I could tell that she was getting hot. The back of my hand brushed against her panty covered pussy and I could feel that the panties were soaked with her excitement. Carol moved her legs wider apart causing the skirt to tighten around her shapely ass. I rubbed her inner thighs between her legs and flicked my fingers over the material covering her vulva. Carol jumped involuntarily when she felt my hand on her pussy.
"Your panties are very wet Carol. Would you like me to take your panties off you?" I teased her.
Carol nodded and gasped, "Yes, please take my panties off."
I eased her panties down over her buttocks, past her thighs and then let them slide to her ankles. Carol stepped out of them and I put them on my desk. I returned to fondling her ass and thighs and I soon had her squirming with desire. Carol moved her body as if she were trying to get my hand near her pussy so I slid it between her legs and stroked the outer lips of her labia. Carol squirmed under the touch an emitted a soft groan. I started to push Carol's skirt up but she stopped me and then she took it off. It was a wrap around mini and she had it off in an instant. She looked so sexy standing there leaning forward slightly on my desk. Her cute ass was framed by her thigh high hose and her short blouse ending at her waist line. She actually looked hotter by keeping the blouse on.
I ran my hands all over Carol's ass, thighs and pubes feeling her wet pussy. I slipped my finger into her vagina and then added a second one. I took some lotion from my desk and I pushed between the cheeks or her ass and massaged into her nether hole. Then I fingered Carol's ass and pussy at the same time. She was going wild with the double penetration and cried out to me.
"That's it finger me, play with me. Make me cum, please make me cum," Carol pleaded.
I continued to work her ass and pussy and within minutes she had her first orgasm. Carol held onto the desk with both hands as her body jerked and spasmed with her climax. I worked my fingers in and out of her holes as she clenched and relaxed her vaginal and anal muscles tightening herself on them. I pulled my fingers from her holes and I stood up behind her. I dropped my pants and boxers to my ankles and brought my rock hard cock to her buttocks. I let it rest against the hot flesh of her ass and I leaned over and whispered in her ear.
"Where do you want it first today? Do you want it in your ass or do you want me to fuck your pussy first?" I teased her and then licked her ear.
"Fuck my pussy first and then my ass. I want you to cum in my ass," Carol murmured.
I then eased my cock into her pussy and fucked her from behind until she orgasmed once again. Then I moved my cock to her ass and fucked her for a short time before I unloaded my semen in her anal canal. Carol looked so hot leaning over the desk with my cock sliding in and out of her asshole that I just couldn't prolong my ejaculation any longer. I leaned over her and she milked my cock dry until it softened and popped out of her ass.
Our sexual encounters in the office usually ended up the same way, with me cumming in Carol's ass but only after she had cum herself two or three times. Carol would surprise me from time to time. One day she leaned over the desk and as I ran my hands up her legs I discovered that she had already removed her panties. Another time she just worked in without her skirt and panties looking very hot in just her hose and blouse. Once she brought one of the dildos with her and put it in her pussy so that when I took off her panties I would find it. Carol liked being fucked in the ass and having her pussy filled with the fake cock.
On days when we would be the only ones in the office I would pick Carol up at her apartment. I would arrive early while she was still in bed and then I would undress and join her. We had morning sex before we left her apartment for the office. On the way home Carol would remove her panties and I played with her pussy. Once we reached the apartment we were both very hot and we went inside and fucked like rabbits. Carol had really adapted to anal sex and I came in her ass at least once every time we were together. She still loved the anal toys as well especially the beads. Carol picked up a unique dildo that had two cock heads on a handle. It looked like a big letter Y. Carol would put one cock in her pussy and the other in her ass for double penetration. Sometimes we would be in a 69 position and she would suck my cock as I double fucked her with the dildo. Carol went wild and juiced all over the fake cock as I filled her mouth with cum. There seemed to be no end to her creativity and willingness to try new things although she had no interest in bringing other sex partners into our relationship.
Our company was acquired by a larger software company and I did very well having an equity position with the firm. Of course most of the administrative jobs were eliminated and only the technical staff was absorbed by the new company. I decided to take some time off and travel around the Caribbean. I love to scuba dive and hang out on the beach. Carol joined me for a couple of weeks and then she planned to return to the twin city area. We stayed at all inclusive resorts with clothing optional beaches while she was with me. We stayed naked most of the time and we had fantastic sex as we brought our sexual relationship to a close.
I never contacted any of the secretaries again nor did they try to get in touch with me. I had terrific memories of great sex and creative encounters. After my six month sabbatical in the Caribbean I ended up back in Corporate America with an Executive position but I still look at the previous seven years as the best in my life for a lot of reasons but the top three were Cathy, Carla and Carol.
By the way I had a great time in the Caribbean and I met some very cool people. I hung out with the dive masters and their staffs most of the time but I also met some very hot ladies on vacation. But that would be another story.
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