tagExhibitionist & VoyeurMy Sweet Ashley and My Boss

My Sweet Ashley and My Boss


If Ashley wasn't an easy drunk, I may have never got to date her in the first place, much less marry her. I met Ashley at a bar in the city five years ago. She was out with friends for a bachelorette party and they were on a 'scavenger hunt' for experiences. She needed a picture of a guy over six feet tall kissing her, and I fit the bill. I managed to get her number before she moved on to a guy a few feet away to get a picture of him spanking her.

I couldn't get her out of my mind that night. The kiss was just 'staged' but she had definitely gotten into it and I couldn't stop remembering what it was like to have her big tits pushed against me...her aggressive tongue probing mine. Ashley was petite, not much over 5 feet tall. She was not the prettiest girl, but she was definitely hot, with big red lips, and blue eyes that could make you forget any girl before her. Did I mention her tits are perfection? So perfect that guys seldom got as far as noticing her smooth legs and firm ass.

Ashley wasn't sure she remembered me at all when I called the next day, but she agreed to go out, and somehow I got her to marry me twelve months later. As it turns out Ashley wasn't really a wild child, she just lost inhibitions after a few drinks. I used that to my advantage when I was horny, or when I wanted to try something new with her. A few drinks and I could generally have my way.

In general though, my Ashley was rather conservative. She consciously dressed to take attention away from her breasts when she went to work, trying to ensure she was taken seriously. She usually wore glasses, and would wear pantyhose until the summer heat became unbearable. She was still noticed (there was no hiding those tits no matter how hard she tried) but Ashley managed to keep her hotness in check more often than not.

Ashley was a social worker downtown, working with underprivileged children. It didn't pay a lot, but she loved doing it. She worked with several other do-gooder women and they seemed to really make a difference in kids' lives.

My work could not have been more different. I worked in Finance and was climbing the ladder at my firm rather quickly, and starting to make a good bit of money. I worked with all men, and was friendly, if competitive, with most of them.

Ashley had met the guys a couple of times when she came to our office, but didn't really know any but Benny, my closest friend in the office. Benny had an obvious crush on Ashley, but he was always a gentleman. Even when we'd go out drinking with Benny, and Ashley would become very flirty, he'd manage to keep his hands to himself, even if he would enjoy an eyeful from time to time.

When I got promoted to head up a division, I promised everyone we would celebrate with a pool party at the house I had bought just a few months earlier. As the date approached the guys in the office were hyping it up, but Ashley was nervous. We had never hosted such a big group before and of course I had told her it was important to make a good impression, especially with Robert, my new boss.

We told people to start arriving around 3pm, and early that afternoon we were putting out some food and drinks for the pending crowd. I noticed Ashley downing a couple of glasses of wine to help relax her. She certainly looked hot, having ditched the glasses and let her hair down. She was covering up her bathing suit with a sarong wrapped tightly around her, one that did little to hide her amazing body.

A couple of guys who worked for me arrived first, both with girlfriends in tow and a couple of bottles of wine. Benny arrived next, and Ashley seemed happy to see a familiar face. She actually greeted him with a kiss on the lips, which surprised both Benny and I. Benny noted how great she looked and joined the others in the backyard.

Soon we had about 20 people at our place. It was a young crowd, with everyone but my boss under 35. It was mostly men, but the girls who were there were all attractive, and wearing very little, so there was a lot of eye candy.

The two girls who got the most attention were also the two who seemed to be drinking the most, Janice and my Ashley. Janice was our new receptionist, a petite Asian who seemed quite comfortable wearing a bathing suit in front of all her new bosses. She and Ashley had made a few tours taking shots around to the group, and they participated as many of them were downed. Ashley soon lost her sarong, and I was surprised to see that she had chosen a red bikini that she was usually too shy to wear on the beach. It gave everyone an appreciation for her large, perky tits, and exposed as much ass as it covered.

As the afternoon progressed I couldn't help but notice that there were a few liberties being taken as Ashley and Janice walked amongst the group. The guys who did not bring dates seemed happy to have the scantily clad girls around, and there were a number of hands that were grazing or even squeezing their asses. I thought I should say something but didn't want to make a scene, especially when I saw Robert, who is the Managing Director of our firm, allow his hand to linger on Ashley's ass for a good length of time. I knew I had told Ashley to ensure Robert was having a good time, and she certainly seemed to be attentive, laughing at his jokes, touching his arm. Robert seemed well tended to, and I was pretty sure I saw a bulge in his preppy shorts as he blatantly stared down at Ashley's tits.

Janice came by with shots and we both had one. She stood very close and I admired her tight little body as she giggled. She whispered to me how lucky I was to have a hot wife like Ashley. I looked over to find Ashley in the crowd and saw her with a group of three men by the pool. Her bathing suit had ridden up her ass so it was almost like a g-string now, exposing both her plump cheeks. I wondered how that had happened and why she didn't notice.

When I saw her head back into the house I made sure I caught up with her and asked if everything was ok. Clearly drunk, with her face flushed she laughed and told me the party was going very well. She said she didn't know how much fun all my work colleagues were, and noted that Robert was very charming. I started to tell her that her nipple was poking out a little from her top but she didn't seem to hear me, and stumbled back outside to join the party.

I stood in the kitchen a while wondering how I could get Ashley to take a break and sober up, but my thought were interrupted by a big cheer. I went to the door and saw a crowd gathered around Ashley and Janice, who were holding each other, their bodies pressed together a little.

"Kiss, kiss!" the crowd cheered.

I saw Ashley bite her lip, then Janice bent forward and the two of them kissed, tentatively at first, then making out passionately. The group went wild, and through the crowd I could see that Janice was groping Ashley's ass. I felt myself harden as I walked towards them, and hoped nobody would notice.

The kiss ended abruptly as I neared and Janice took Ashley by the hand while the two of them jumped in the pool. A few guys and girls jumped in to join them and the party was clearly in full swing. There was an attempt at a water polo game, but is devolved rather quickly. Benny and Alex, a new guy I had just hired to work for me, started to playfully wrestle with Ashley and Janice, dunking their heads below the water. I couldn't see everything that was going on but I did hear Janice say something about Benny being 'so big' and thought I saw Ashley reach under the water to Benny's trunks, before she giggled and suddenly swim away.

Ashley started to come out of the pool, but Alex grabbed her waist to pull her back in. This resulted in Ashley's ass pushing back into Alex's face for some time before she fell back into the water. The two of them laughed as Ashley tried to get away. When she finally did escape his grasp, she had lost her top, and was covering her tits with her hands. She called for Alex to throw her the top but he swam further away laughing. Ashley walked up the stairs of the pool with her little hands pushing her big boobs together as she covered he nipples.

Ashley reached for a towel, but when one of the guys pulled it away Ashley laughed and said, "OK, well I guess you've pretty much seen them at this point."

She dropped her hands to her side and both of her beautiful wet breasts were there for everyone at the party to see. All of my colleagues were seeing my wife completely topless; practically nude given her bottoms barely covered anything. She seemed to enjoy the attention as the men toasted her. I brought a towel, but she shrugged it off and walked calmly back to the house, her barely covered ass swaying.

I followed Ashley inside, nervous that she might be angry. When I found her in the kitchen she gave me a big smile "What a crazy party, right? You must be happy, I have really tried to make sure everyone has been entertained!"

I thought she might be angry or joking and started to interject but Ashley went on, talking fast and slurring slightly "I know you might think I am being very flirty, but you wanted me to make everyone happy right? I didn't expect your friends to be quite as grabby, does my ass have marks from all the hands that have been on it?"

Ashley turned around and thrust her ass out a little, pulling the bathing suit completely up her ass crack, as if she needed to do so for me to see any fingerprints. She turned and looked at me over her bare shoulder, and I could see her one large tit heaving, her nipple hard like it always was when she was aroused.

"You know, I think Robert really likes me!"

I looked at her standing before me, looked down at her ass, which was now only essentially bare, and I got hard just looking at my wife. I wanted to tell her to put on some clothes, that she didn't need to...but no words would come out. Ashley kissed me on the cheek, brushed her hand against my cock, and then headed back out to the yard with another bottle of wine.

I stayed inside a moment, trying to collect my thoughts, trying to let my erection subside so I wouldn't shock my colleagues. When I got back out I noticed that many people had already left the party, perhaps concerned with the turn it had taken. There were now just a few remaining...myself, Benny, Alex, Robert, Janice, Ashley. I wondered if I had done damage to my career, but when I saw Robert smiling broadly and laughing at something Ashley said I felt reassured that he was in good humor. Benny was snuggled close to Janice in a lawn chair. Robert and Alex were sitting and chatting with Ashley, who stood above them with her tits out despite the fact that she could now easily cover up. Her bathing suit remained pushed up her ass crack, and I saw Alex, who was clearly drunk, lean forward and make no effort to hide checking out her ass, so close that I wondered if Ashley could feel his breath on her cheeks.

"Why don't you run inside and fetch us some scotch Andy?" Robert asked, breaking me away from my thoughts.

He took Ashley by the hand and had her sit down on the chair right beside him, so close their bare skin touched. I flushed with anger and embarrassment, but as I watched Robert place his big hand on Ashley's knee I felt myself harden again and decided it would be better to excuse myself.

As I poured the scotch I tried to steel myself to be stronger and extract Ashley from the situation. I played out how to avoid a scene. When I came back out with six scotches on a tray, I was shocked to see the three men lined up in one chair, with the two girls turned away from them, their asses thrust out obscenely.

"Andy! Just in time!" Robert bellowed. We were having a 'best ass' contest and it's a tie. I picked Ashley, Alex picked Janice, and Benny here refuses to choose. So you're the tie breaker."

Robert pointed to an empty chair and I dumbly put the tray of scotches down and sat where he indicated. "Go ahead girls" he ordered.

My wife and Janice both obediently walked over to me, turned and showed me their two gorgeous asses. I felt my head spin a little from the alcohol and excitement, and felt a stirring, as I became to harden yet again. "Janice you are going to have to go the extra mile to get Andy to vote against his own wife!"

Janice looked down at me, and moved her ass even closer. Her hands reached back and she slowly lowered her bathing suit bottom, exposing more and more, until her bare bottom was almost pushed into my face. I felt my cock push against my bathing suit. I couldn't take my eyes away as Janice ran her hands on her ass cheeks and I licked my lips involuntarily when she slowly parted them so I had a close-up view of her perfectly waxed asshole.

"I guess we have a winner!" Robert exclaimed with a hearty laugh.

Ashley playfully threw her drink at me "Thanks a lot Andy."

Janice, who had not yet lifted her bathing suit back up, gleefully cheered and threw her arms around my neck. I looked around her to see Ashley walking away with Robert. His arm reached around her and rested on her ass cheek

"Never mind, your ass is perfect to me" he said reassuringly and he gave it a squeeze to reinforce his point. "Does Andy pay enough attention to your ass?"

Ashley shook her head and put out her lower lip in a dramatic pout. "Oh that just won't do..." Robert said, his hand now exploring her ass in earnest "an ass like this needs to be worshipped."

With that Robert sat, then turned my Ashley around. He positioned her so she was bent over, her ass presented to him, which she did very willingly. Janice sat beside me to watch and I wondered why I wasn't saying anything, why I remained rock hard watching my wife do my boss' bidding. Robert kissed my wife's ass softly, then repeated the action on her other ass cheek. Ashley looked over at me and smiled, seemingly pleased to giver herself to a stranger like this. I knew she was very drunk, but did she really think this was all for me?

Robert's kisses on my wife's ass grew hungrier, and as he started to lower her bathing suit bottoms I knew I had to say something. I started to find the right words when I felt Janice's hands run up my thigh, then on to my cock through my bathing suit. She squeezed and started to stroke me and I couldn't find the will to stop her. I told myself that this had to stop as I watched Robert pull Ashley's suit off. She was now completely nude, and the center of attention of four of my work colleagues.

Robert returned to the task of kissing my wife's ass, but was now more focused on her ass crack. I watched him tongue Ashley's asshole, something she had never allowed me to do. While I watched Janice's hands expertly undid my bathing suit and I felt the amazing sensation of her smooth little hand stroking my bare cock. I thought of Alex and Benny and wondered what they must think of me sitting like an idiot watching my wife with my cock out, but I couldn't take my eyes way from Ashley to see their reaction.

Robert paid me no mind at all as he now stuck two fingers up my wife's wet pussy. Ashley moaned and arched her back even more for him. She turned to look at me and smiled with a knowing look as she saw me sitting there, Janice giving me a slow hand job. She reached back and pushed Robert's face into her ass and I wondered how far his tongue must be up her by now.

Robert stopped stroking and stood behind my wife. He quickly dropped his shorts and pulled out his large cock. I swallowed hard, knowing I had to stop my boss from fucking my wife, even though the idea (and Janice's hand) had me so close to climaxing. Instead of entering Ashley, however, Robert placed his hard cock on her ass crack and started to rub it up and down her. It looked just as though he was fucking her from behind, and Ashley somehow seemed more into it than she ever seemed to be into fucking me, even when drunk.

Robert's cock appeared dangerously close to entering my wife's asshole a few times, but he stayed just along her ass crack.

"Andy, you have a helluva gal here" he said with a patronizing tone between grunts.

"You're pleased, right?" Ashley pleaded.

I was unsure if this was to Robert, or me but at that moment I could no longer hold back from cumming, all over my bathing suit and Janice's hand. I closed my eyes with the intensity of everything happening, and when I opened them I saw Robert pulling his bathing suit up, my nude wife still bent over for him, cum dripping off her back.

"I have to run" Robert said in a matter of fact voice, looking quite composed. "Ashley, I know we'll be seeing more of you going forward. Be sure to drop by the office." He gave me an unexpressive look, patted Janice on the ass, and left to get his car.

I feebly thanked Robert for coming and wondered how to get Alex and Benny to leave before any further advantage was taken of my wife.

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