A Most Memorable Bottom

PRELUDE

I have always been a leg and ass man. Big tits were not important to me in fact I like the smaller to medium sized tits. However if a girl had large breasts along with a great ass I was cool with that. The most important thing to me though was a shapely ass. It was just something about the curve and lines of the female bottom that I found alluring. Since graduating from college in 1963 I have been fortunate to date many girls who took to anal sex. There were even a few who gave me their anal virginity. I remember all of them quite well.

First it was Charlotte a short hair brunette with nice tits, shapely legs and a killer ass. She loved anal and we always finished up that way. First I took good care of her pussy and then I took her ass. She liked the spoon position with both of us on our sides. My left hand would fondle her breasts and tweak her nipples while my right hand fingered her pussy. I filled her ass with my cock and fucked her until I came in her ass. She loved the feel of me cumming in her.

Another girl who I saw occasionally was Pam and she liked to do it all. She gave great head and was good in bed. She had brown hair done to her shoulders, medium size tits and a large round shapely ass. Pam always liked to watch when I fucked her ass. She positioned herself on all fours on her bed so she could see us in the mirror over her dresser. Pam also liked it when I filled her rectum with my seed.

I was going for my MBA attending night school when I met Bonnie. She had short light brown hair 35B tits and an ass to die for. It was funny with Bonnie as she always said that she didn't want to do it. Every time I was in her ass she would whisper that she really didn't want to do this. However she never resisted and every time we dated I always fucked her ass and came in her. She actually orgasmed once when she was on all fours and I was balls deep in her ass. I fondled her impressive tits and she had a massive climax.

Beverly came onto me one night when I was at a club. I didn't know it but her husband was out of town and she had ditched her wedding ring. We ended up back at my place and started out in a 69. Next I fucked her missionary style and then doggy style. I played with her nether hole and she told me that she liked anal but to use plenty of grease for my ass buster. I assumed that my cock would be the biggest to go there so I lubed her anus and my cock thoroughly. She was tight and it didn't take me long to cum. I stayed in her and kept fucking her ass until I came again. I saw Bev once more after that first night and then later I learned she was married and I stayed away.

I met Jerri at a seminar in Chicago. She was a cute slender girl with light brown curly hair. Jerri had smallish titties that were cute, a flat tummy and nice legs. Her ass was round and protruding which was pronounced on her slender form. We slept together and I discovered that she had a vagina that did not go very deep. Afraid of hurting her, I ate her pussy and rubbed the head of my cock on her clit. She reciprocated by giving me head but wished she could do more. We discussed anal and she was willing to try. The next night I took her anal virginity and fucked her ass for two more nights. She gave me her address and phone in New York in case I ever got there.

There were others too; Lee, a Texas girl who was 5'11" with a knock out body. I can still visualize her on all fours with her long blonde hair and big tits hanging down as I drilled her curvy bottom. Sherry another buxom blonde who I met in Aspen and Carol a petite brunette from Detroit both loved anal. Barb a secretary in our home office in Philadelphia was a 36 year old with a great looking ass.

I had moved up the corporate ladder and took over a department. My secretary was an attractive blonde with short hair. She had small tits, muscular but shapely legs and the most wondrous ass I had ever laid eyes on. Cathy worked for me for two years before we started our affair which lasted three years. Our favorite place to have sex was at a romantic interlude that had a Jacuzzi and a water bed. She loved to have me rim her anus in the Jacuzzi. Cathy always showered and douched her pussy and ass before we had sex. I always remembered her on all fours with her head down turned to the side. Her back was arched emphasizing the shape of her marvelous bottom. I would kneel behind her and ease my cock into her ass and she would say, "Oh you make me like this more that the regular way."

I always took good care on Cathy's pussy and she seemed insatiable. I loved it at the interlude when she rode my cock and I could look into the mirrors and see her curvy ass. I fondled her buttocks and teased her anus as she rode my cock. After several orgasms I moved her to all fours and fucked her lovely ass until I filled it with my seed. Cathy had the most alluring and desirable ass that I had ever seen and fucked. That is until I met Bridgette.

A search firm presented me with an intriguing opportunity in San Francisco. I checked it out, interviewed several times and ended up accepting the position. I offered Cathy the chance to come with me but she had too many ties in the Atlanta area. It was 1976 when I left my former employer and moved to San Francisco. At that time I was 34 years old. I took over a division that was a mess and I knew it would be a challenge to get it turned around. It was also going to be a challenge to get the staff to buy into my approach and to find people I could trust.

Fast forward two years later when I came home to my condo after a late board meeting. Bridgette who had recently moved in with me was not in the great room. I walked into the bedroom and she was naked on all fours with her incredible ass pointing in the air. I stripped off my clothes and approached the bed. I could see her nether hole as it appeared to pucker and twitch in anticipation of the penetration that was to come. I knelt behind her and stared at the lovely ass that I was about to enjoy once again.

I'm getting ahead of myself here. Let's take it back to when I first met Bridgette.

SETTLING INTO THE NEW JOB

The first week I had meetings with the IT management and key stakeholders in the company. I learned very quickly that there was a huge gap between the company business plan and the IT objectives. The administrative assistant for my position was a very attractive Eurasian woman named Bridgette. She had been in that position for five years and she was apprehensive about my role as the CIO. Over the next three months I found Bridgette to be very capable, loyal and professional. She proved that she could handle sensitive and confidential information.

Bridgette was 28 years old and she had a very slender but shapely figure. She was 5'5" tall and I estimated that she weighed about 110 pounds if that. Her skin was flawless and she had deep dark mysterious eyes to go with her shiny black hair. Bridgette always wore her hair up in a bun and she always wore tailored suits to the office. Her skirts were cut just above the knee and showed off her shapely legs. The suits were snug enough to show off the swell of her small breasts and the contour of her curvy ass. Her mother was Japanese and her father was French. She was drop dead gorgeous and in time I would learn how skilled she was in the bedroom.

My normal workdays started at 7:00 AM and I stayed in the office until 7:00 PM. I also took the time to meet with second and third shift people at the data center. My typical day was to workout at 5:00 AM; shower, dress and eat breakfast at 6:30 AM; spend 12 hours at the office and then have a light dinner at 7:30 PM. After dinner I usually returned to my hotel room and did more work until 10:00 PM. There was something about being the first to arrive and the last to leave the office that got the attention of other executives and my staff.

The first month was non-stop work including Saturdays and Sundays. At the start of the second month I began to enjoy some of the city on the weekends. I loved wine and I made a number of trips to the Napa valley. At 34 years old I was in very good shape as I had always worked out and watched my diet. I was 6'2" tall and weighed 185 pounds. I was not normally a runner but I had gotten into the habit of jogging in the morning.

By the end of the second month I had completed the IT baseline assessment and I had started the strategic planning process. Once the strategy was prepared that would define the organization restructuring. I counted on Bridgette to maintain confidentiality of all information as I knew that staff members would try to pry information out of her. Bridgette proved herself worthy of my trust and our mutual trust for each other grew.

The day for the presentation to the executive management and the Board arrived at the end of the third month. Bridgette and I worked tirelessly on the presentation and I felt I was as ready as I could be. I first met with the executive team that morning in a two hour session and everything went extremely well. Next it was the board meeting at 4:00 PM. Bridgette remained at the office in the event I needed something at the last minute for the Board meeting. I entered the Board Room at 4:00 PM and sat through the normal Roberts Rules of Order protocol. Then I started my presentation at 4:30 PM. The presentation was thirty minutes long and to the point but the Board members drilled me for another hour.

At 6:00 PM after further discussion the Board approved the IT plan and proposed organization restructuring. However they placed a condition on the approval and that was that I had to lead the effort for the first two years of plan implementation. I was stunned by the Board's conditional approval but I knew that I had to accept. I told the Board that I accepted the assignment contingent on my firm's approval the next day. I already knew however that my superiors would approve the deal.

As I walked back to my office it then dawned on me that I would be living in Oahu for two years. It was almost 7:00 PM when I got back to my office and Bridgette was still there waiting in case I needed her. She was thrilled when she heard that the Board approved the plan. I was excited too and I looked at Bridgette and told her it was time to celebrate a little.

"Can I buy you a nice dinner?" I asked.

"I would like that very much," she said politely as she blushed.

"You pick the restaurant," I insisted.

Bridgette told me about one of her favorite restaurants so we decided to go there. The restaurant was an excellent seafood restaurant that served many Japanese prepared dishes. Bridgette educated me on the different menu items and we sampled many food items. We had a fine meal with some excellent wine and I enjoyed her company all evening. It was 9:30 PM when we arrived back at my hotel and I invited Bridgette in for a night cap. I was actually surprised when she accepted.

A FANTASY COMES TRUE

Bridgette was a white wine drinker so I took a bottle of white for her and a bottle of red for me from the mini bar. I poured the wine for us and Bridgette and I toasted one another. As we drank the wine and chatted about the Board approval and the future Bridgette kicked off her high heels. She looked at me quizzically and then spoke.

"I hope you don't mind but my feet are killing me from wearing those heels all day," she said almost apologetically.

"No not at all, get comfortable," I replied and I sat down on the sofa leaving a seat cushion between Bridgette and me and then I offered to massage her feet.

"I give excellent massages, how about a nice foot massage?" I really announced rather than asked. "Just stretch your legs out on the sofa," I instructed.

Bridgette held her skirt close to her thighs as she swung her shapely legs upon the sofa in my direction. Her legs were beautifully shaped and I wondered what was at the end of her pretty gams. For the first time I looked at Bridgette in a sexual manner and I had this sudden desire to make love to her.

I began to massage one foot and Bridgette sighed, "Oh that does feel good!"

I worked on her one foot for a while and then placed it right in my crotch as I picked up her other foot. As I massaged her other foot the one in my crotch was pressed right against my erect cock. I knew Bridgette could feel it and that she knew what it was. My cock throbbed and I was sure she could feel it pulsating against the sole of her foot. I massaged the other foot and Bridgette just sighed and cooed in relaxation.

"How about your calf muscles I bet they are tired as well from the high heels?" I asked.

Bridgette didn't answer but she didn't protest either when I began to massage her calves. I rubbed the calf of one leg while the foot of the other leg remained in my crotch. Bridgette took another sip of wine and tilted her head back and closed her eyes. I worked all the tension out of one calf and then started to work on the other one. Bridgette kept her eyes closed and her head back as I massaged her shapely legs. Occasionally she would pick up her head, sip some wine and smile at me before closing her eyes again.

I didn't ask her permission as I let my hands move up to her thighs and massaged her quads. Bridgette jumped at the first touch of her thighs but I told her to relax and let me work out the kinks. As I massaged her thighs I pushed her skirt up higher and I could see her panty covered crotch. Bridgette was wearing her panties over garter belt. I let my hands wonder all over her thighs as I massaged her inner thighs as well. I could clearly see a wet spot had formed on Bridgette's panties.

Bridgette kept her eyes closed as I massaged her thighs and I decided to take it to the next step. I moved my hands above her stockings and caressed the naked skin. Bridgette flinched and opened her eyes to stare at me. She still didn't protest but she looked worried. I ran my hand over her panty covered pussy and she almost leaped off the couch.

"Walt please stop you shouldn't do that," she gasped but I continued rubbing her bare thighs and panty covered pussy as I was now overcome with desire.

Bridgette was breathing hard and she seemed confused when she spoke again, "Please stop before this goes any further. We are going to be working together and we need to keep our relationship professional." She was breathing hard and she did not sound convincing. I was sure that she was ready to have sex.

I pushed Bridgette's skirt up to her hips and leaned over 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 lifted Bridgette's legs to my shoulders and kissed her inner thighs just below her panties. She groaned with pleasure as she reached down with her hands to control my head. Bridgette 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.

Bridgette 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. Bridgette 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. Bridgette was really excited as her erect clit looked like a teeny dick sticking out. I sucked on her hard clit and she bucked her hips up into my face. I reached under 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, 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 all over the sofa. I kept right on eating her pussy and I held onto her shapely ass as she thrashed about. Bridgette slowly calmed after her intense orgasm and I continued to lick her until her pussy was dry. As we lay on her sofa I continued to lick and kiss her bare thighs above her stockings as she ran her hands through my hair.

"Oh that was something I really came hard. Thank you, thank you!" she murmured.

I peeled off her panties leaving her stockings and garter belt on her body. Bridgette watched me as if she was in a trance as I pushed my pants and underwear down to my knees and my rock hard cock leaped out. Her eyes opened wide as if she was afraid when she saw my eight inch cock. 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 sofa and proceeded to feed my thick cock to her.

"Oh, oh yes, oh it feels so good, oh, oh, love me, make love to me," she cried.

I slid in and out of her pussy slowly allowing her to adjust to my size and I continued to go deeper with each thrust until I was buried balls deep in her pussy.

"Oh I have never been so full, love 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. Bridgette had multiple orgasms as I fucked her. I pulled her blouse out of her skirt and pushed it up over her bra. Then I reached under her and unhooked the bra and pushed it up over her tits. She had small pretty firm tits with dark rock hard nipples that extended a ½ inch. 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, I love that!"

I could feel my balls start to tighten and I knew it wouldn't be long before I filled her pussy with my cum. Bridgette stiffened and then had another violent orgasm.

She yelled, "Hold me, please hold me, I'm cumming!"

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 cum in there mingling with her own juices.

"Are you okay, Bridgette?" I asked her.

She nodded that she was okay and then 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.

"I'm not big, maybe above average but not that big," I responded.

"Maybe by your standards you are not big but you are big," she said as she held my cock lovingly.

"Want to go to bed?" I asked her.

Bridgette smiled at me and nodded her agreement. She sat up let her hair down. Her silky black hair cascaded down to her shoulder blades. She looked very exotic. We stripped off our clothes and Bridgette 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 beautiful woman all night. I fucked Bridgette as long as I could before I shot my second load of the night. 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 want this to go on forever but I need a rest. I am not sure I can cum anymore."

"Are you up for a shower?" I asked.

"I'd rather sit in the tub," she replied.

I ran a hot bath for us and put the hotel supplied shower gel in the water. We both bathed together and as I caressed her body Bridgette 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 stroking her curvy ass and her hot pussy. I startled Bridgette when I slipped a very slippery 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 bath we dried each other off with huge terry cloth towels and as she was drying me, my cock was at full attention.