8 comments/ 93950 views/ 74 favorites My Sweet Ashley and My Boss By: writemarksmith 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. My Sweet Ashley and My Boss Ch. 02 Over the weeks that followed my party, Robert never directly confronted me with the fact that he had cum all over my wife, but our dynamic had changed. Robert had always been a rather demanding boss, but now he had a bit of a sneer when he told me to get a report to him. He would sometimes have me get him and others coffee when we were going to have a meeting. Overall I was happy to have a job and certainly didn't want to protest the small indignities. It did bother me when our receptionist, Janice, who along with others had seen Robert shame me, would giggle with the other secretaries sometimes when I walked by, but...well maybe they were laughing about something else altogether. I avoided happy hours and focused on my work. My wife Ashley didn't want to discuss the party at all. She fell asleep soon after Robert and the others had left and the next day she had a big headache. She groaned that she had had too much to drink and needed to be better next time. I wanted to confront her, but I could see she was regretful and I didn't know what to answer if she asked why I hadn't stepped in. Ashley seemed to go right back to being the rather prim, sweet wife she had always been, trying hard to hide her figure every day when she left for work. The incident always crept into my mind when I fucked Ashley, actually making it somehow more exciting, but otherwise I tried hard to forget about it. My concerns came rushing back, however, when Robert told me that I should bring my wife to a dinner Friday where we were to woo a key prospective new client. I thought I saw a sadistic smirk when he told me she must be there, but told myself I might be imagining it. I felt better when he also told Alex, a colleague who worked for me, that he should also bring a girl. It was going to be the five of us, with a clear objective of impressing the client and sealing the deal we had been working on. Ashley didn't seem concerned about the dinner, other than choosing the right outfit. When she put out two and asked me which I preferred I chose a nice long blue dress I thought she always looked elegant in. She went with the short black dress saying it was more in fashion. I told it it showed a lot of cleavage but she dismissed my protest. Ashley seemed to take more time getting ready that she usually did, including a long shower, lotioning all over her body, and matching black lingerie with the dress. She certainly would impress tonight, although I still thought she might come across as a bit too sexy. Robert had ordered us a limo to the dinner, which impressed my wife. While we waited she had a glass of wine and I reminded her how important the dinner was. She promised she would be on her best behavior and would be sure to help make the clients feel confident they were making the right choice. The limo was fully stocked and Ashley poured us each a glass of whiskey on the ride. I reminded her she had to watch her drinking but she told me I had to to lighten up. After all, she implored, how often were we going to get to ride in such a nice limo? She said again how nice it was for Robert to arrange this for us, and I felt a pang of jealousy as we toasted to a fun evening. As it turned out we were the last to arrive to the private room that Robert had booked. As we entered the room I immediately noticed that Alex had brought Janice as his date. Janice, a petite Asian firecracker, looked even more smoking hot than usual in a flouncy short red skirt and a white blouse unbuttoned to show off her minimal cleavage. I had to refocus as I saw Robert approach us with a booming welcome. He kissed Ashley on the cheek, then shook my hand and introduced me to Mr. Kansaki, the Japanese investor Robert wanted to close tonight. Kansaki-san was a small man who wore glasses. He looked serious as he shook my hand, not returning my smile. I was about to introduce Ashley when I saw that Robert had taken her by the hand and walked her towards Mr. Kansaki. He introduced her as Andy's lovely wife and I saw his hand reach around to the small of Ashley's back and gently push her towards the Japanese man. Mr. Kansaki was shorter than my wife, so he had a perfect vantage point to enjoy her ample cleavage, and he seemed to make no attempt to hide that he was doing so. He shook Ashley's hand with a tight smile and told her she was indeed beautiful. While I was watching Ashley, Janice and Alex had walked over to greet me. Alex gave me a quick pat on my shoulder, then Janice surprised me with a kiss on the lips. I flashed back to the hand job she had given me while I watched Robert take advantage of my wife. I felt myself flush in suppressed anger (mostly with myself), but also with arousal. I couldn't deny that I was already hardening just a minute after arriving. I watched Ashley's ass as she walked away then saw her greet my wife with a kiss on the cheek. Janice then whispered something in Ashley's ear, and I remembered the two had actually shared a pretty passionate kiss at the party. I wondered if Ashley even remembered that. It was clear that every eye in the room was on the two of them. Robert brought red wine to the girls and Alex and I poured a scotch from one of the bottles on the table. Alex started to chat with me about the game coming up that weekend, but my mind was drifting. I became even more distracted when I saw Robert's hand disappear behind my wife's back. I was pretty sure he was feeling her ass, but I was in no position to do anything about it without making a scene. Ashley certainly didn't seem to mind if Robert was groping her. I realized she was half way through her third drink and we had just started the evening. I had to make sure she didn't get out of control again. Alex nudged me to bring my attention to Janice who was flirting pretty aggressively with Mr. Kansaki, even making the dour man smile and laugh a little. She even showed him the tattoo she had on her leg, which required her to hike up her short skirt a little more. Mr. Kansaki was clearly charmed and called out for another round. I looked around and realized that the waitress was not in the room. With nobody else making a move, I poured more wine for Janice, more scotch for Mr. Kansaki, and brought it to them. While Janice gave me a quick smile, Kansaki-san never as much as looked at me, keeping his eyes on Janice. I looked over at Robert, hoping he'd see how I had proactively addressed the need, but he was focused on my wife. From where I now stood it was clear his hand was indeed on her ass, cupping it. I felt my cock involuntarily twitch and harden a little. I thought I might say something as I watched how close they were standing, saw his hand squeeze her ass cheek without any protest from my wife, but at that moment the waitress came back in and Robert decided it was time we were all seated. Robert sat at the end of the table, seating Mr. Kansaki between the two girls. Alex and I sat across from them. I saw Robert pour another glass of wine for Ashley, who was also seated by him, and wished I could shout out for her to slow down. Three drinks would already have her quite drunk, with four all bets would be off. Robert made a toast welcoming our guest and told the waitress we would order food later. The music in the room made it a little difficult to hear the conversation, but Mr. Kansaki continued to chat up Janice. It appeared that Kansaki-san had his hand exploring Janice's bare leg, which I remembered to be extremely smooth. Ashley apparently decided to make it a bit of a competition as she cut in on the conversation. I heard her saying something nice about Mr. Kansaki's jacket, which appeared to please him. Soon the two girls were leaning in to hear the soft spoken Japanese man, who now had one hand on each girl's legs. Alex noted to me how good the girls were at buttering the old man up. I agreed, but inside I was frustrated that he just brought the receptionist to be fondled by the old man while I had to offer up my wife. I sat nursing my scotch while I watched Ashley finish her drink. At one point I saw Janice jump a little then playfully slap Kansaki-san's hand under the table but her giggling seemed to belie any real concern. Mr. Kansaki's hands stayed under the table, one on Janice, the other on my wife. Robert seemed pleased with the evening's progress if a little drunk. He made another toast, this time to the lovely ladies with us this evening. Janice and my wife beamed with the attention and we all drank. Robert got up, fumbling a bit, and walked behind Mr. Kansaki, slapping him on the back. Kansaki-san seemed a bit put off but Robert took no notice. Robert loudly noted how amazing it was that beautiful women could look so very different. He walked behind Janice and talked about her tanned skin, her dark hair and her tiny, perky tits. He the reached over and cupped the tit closest to Mr. Kansaki and said how nice it was even if it were small. Janice did not give any indication she thought it was inappropriate for Robert to be holding her tit and talking to a client about it. Kansaki-san laughed and said how different American women were from Asians. Robert agreed heartily and walked over to Ashley. He reached down casually lowered her dress straps then cupped both of my wife's large breasts, exposing her lingerie as he pushed them over her little dress. Kansaki-san actually clapped at the presentation, reaching over and squeezing my wife's tit himself. I felt completely powerless sitting across from two men groping my wife's tits and only watching. Ashley was laughing loudly as the two men went on about how white and creamy her tits were and how they were the real symbol of what America stood for. Robert said that tits were not a very fair competition, but he knew one that would be more interesting. He stage whispered that both girls had amazing asses and that they had in fact competed before for who had the best ass. Janice and Ashley both giggled and Janice slapped her ass temptingly. Robert asked Mr. Kansaki if he would like to judge a rematch and Kansaki-san seemed over the moon with the idea. I knew it was time to step in and I stood up to put a stop to it, but Alex stood with me, and drowned out my objection with a loud cheer. Alex then pushed me back into my chair with a stern look that took me by surprise. I was Alex's boss, but now he was giving me orders?! Or was he just being a friend trying to prevent me from losing my job? Either way the contest was on and both girls were standing and giggling as Robert turned Mr. Kansaki's chair around. Ashley told Janice she had to go first, perhaps remembering how Janice had taken advantage of going second in their previous contest. Janice did not need to be asked twice. She turned her back to Mr. Kansaki and started to sway her hips in a mesmerizing fashion. She then started to lift her red skirt very slowly revealing her tiny red panties inch by inch. Every eye in the room was on Janice's ass, the curves showing on one ass cheek, then the other. Finally she unzipped the skirt and let it drop to the floor. As Janice started to move her ass closer to Mr. Kansaki, the door opened and the waitress started to come in our room. Everyone froze as Robert rushed over to intercept her. There was a hushed discussion then I saw him hand the waitress some cash as she left. Robert nodded to Janice, who started back into her dance, now wearing just her blouse, small panties and red heels. Janice moved her ass ever closer to Kansaki-san, teasing him as she swayed. Finally she bent forward and ever so slowly peeled down her panties. Mr Kansaki stared intently, his face inches from Janice's now bare ass. Janice stepped out of the panties, brushing her ass cheek against the Japanese man as she did so. She swayed some more as Robert and Alex cheered then reached down to place one of Mr. Kansaki's hands on each ass cheek. He squeezed and groped happily as Ashley and the men cheered him on, until finally Janice moved away, turned to give us all a view of her exposed pussy, and gave him a bow before moving aside to put her panties back on. I was so hard from watching Janice and her beautiful bum that I had almost forgotten what was coming next...my wife's turn. My wife smiled at Janice, smacked her bottom hard, then walked to Mr. Kansaki, standing above him, looking down. Kansaki-san looked like a wolf staring at a meal about to be devoured. I could see Ashley was drunk with bright red cheeks and a bit of a stagger, and I feared she was going to try to top Janice. Ashley put her knee into Kansaki-san's crotch as she leaned into him, pushing her cleavage into his face. Janice protested Ashley using her tits, but Robert and Alex cheered her on. Mr. Kansaki started to kiss her chest. Robert gave Ashley's ass a familiar squeeze, then pulled her dress top down and pulled one of her tits out of her bra. Ashley's big pink nipple was right in Kansaki-san's face, and he immediately started to suck on it greedily. I knew Ashley loved to have her tits sucked but was amazed she was letting this old man do it in front of everyone. Ashley closed her eyes and pulled his head into her, then finally broke free, shaking her finger at him in a teasing way. It was clear she was getting off on all the attention. Ashley now wobbled on her heels as she pulled her dress down and let it fall to the ground. I had been concerned that she was showing too much skin in the skirt, but now my Ashley was standing in just her black panties and matching bra, with one tit already exposed. Ashley turned and Mr. Kansaki finally got to see the competing ass. Robert reached over and pulled Ashley's panties up her ass crack to make it a thong. Her ass was much larger than Janice's but it looked round and delectable as she danced for the old Asian man. Ashley slapped her ass in front of him, then bent forward inviting him to do the same. Kansaki-san swatted hard, harder than I ever do when we played with spanking, and Ashley let out a delighted squeal. He spanked her three more times on the same cheek leaving it bright red and Ashley only pushed her ass higher and closer for him. With the panties riding up she was now exposing some of her pussy lips to the old man and everyone else watching. I could see that she was wet even from across the table. Ashley turned around and whispered something in Mr Kansaki's ear then presented her ass to him again. He bent forward and started to pull her panties down with his teeth. He took his time, my wife's ass pushed into his face as he struggled to move the panties down her big behind. After he had exposed most of her bottom Ashley helpfully reached back and pulled them down the rest of the way. She stayed bent over, showing the man her big beautiful ass, and even presenting him her asshole. Ashley's puffed pussy lips were also well exposed as she now just clumsily wore a bra and heels. Mr. Kansaki actually let out a whoop and kissed each of her big ass cheeks. Janice admitted defeat and walked over to give Ashley a kiss. My wife stayed bent over as she kissed the Asian hottie and Kansaki-san took full advantage deciding to put a finger into my wife's pussy. I saw Ashley jump a little with shock, but she continued to make out with Janice. I was angry and ashamed to have my wife molested like this in front of everyone, but I was also incredibly turned on. Without even realizing it I was stroking my cock through my pants. Ashley removed her lips from Janice's, and gently pulled Kansaki-san's hand away. She then causally spread her bare ass cheeks over the tent in Mr. Kansaki's pants and started to rock back and forth on him. Robert and Alex cheered her on and from my angle it looked like she was fucking him reverse cowgirl style, but I was pretty sure Mr. Kansaki's cock remained in his pants. Kansaki-san grabbed my wife's big tits. Both were now exposed. Finally the rocking slowed down as Kansaki-san's groans and Ashley's whimpers almost drowned out the cheering. Kansaki-san slumped back in his chair looking sated and very happy. As much as the scene had turned me on I was glad it was over. I needed to get Ashley dressed and take her away from here. We could talk tomorrow after she sobered up. I looked at her as she got up from Kansaki-san's lap, wearing only a bra around her waist and heels. I started to walk over to her but I stopped when I saw Robert walk to her and put his arm around her waist, telling her what a good girl she had been. He gave her a glass of whiskey which she downed immediately with a cheer. He then told Ashley she had really gotten everybody worked up and she really shouldn't leave the boss with blue balls. He took Ashley's hand and moved it so she was grabbing his cock through his slacks. What happened next was a surprise that changed my relationship with Ashley forever. Ashley turned to me with her big eyes and asked me if I would mind if she gave Robert a little relief. She looked at my hand, still stroking my cock through my pants and said "It looks like you might actually enjoy seeing that!" I couldn't get any words out of my mouth. I felt every eye on me, and saw that Janice was watching me with a big smirk. I looked at my wife, looking so sexy standing there nude with her hand on another man's cock and I nodded dumbly and hung my head a little. Ashley smiled at me with a look I had never seen in her eyes before...then went to work unzipping Robert's slacks. She knelt before him, and took his large cock in her mouth. Alex and Janice cheered my wife on as Kansaki-san enjoyed the show. I was sure she was giving him head much more enthusiastically than she had ever done with me. Robert grabbed her hair and roughly moved her head back and forth along his member. Finally he was clearly about to cum and as he groaned my wife tried hard to swallow every drop. When Robert pulled out of her mouth she stayed on her knees, looking a little dazed, a little of his cum dribbling from her mouth. Robert laughed, zipped up his pants, and told Kansaki-san they could go enjoy a steak down the street. The two of them left without a goodbye, although they both gave Janice, still in her panties a slap on the ass as they walked out. I wondered how to get my wife dressed, what to do about the bill, and whether the waitress would soon come and be shocked at the scene. Mostly I wondered what would happen in the days and weeks to come as it seemed there was no going back from this. My Sweet Ashley and My Boss Ch. 03 In the days that followed watching my wife giving my boss a sloppy blow job it was clear the dynamic of my relationship with her had changed. I was too ashamed to bring up the incident given that I had agreed to let her give him oral sex. I knew she had been drunk, and she was just trying to make everyone happy. Ashley didn't bring it up directly, but it seemed like there was multiple allusions to what had happened. Ashley now seemed to be good friends with Janice, the Asian cutie who was a secretary in our office and had seen me humiliated twice by my wife with Robert. I would hear her giggling with her on the phone in the other room and when she would be texting back and forth with a smile she would tell me she was texting Janice. I would change the subject since any talk of Janice would lead back to how submissive I had been to my boss and to my wife. We had sex with some frequency and it was actually quite good. Ashley did tell me to get her wine to 'loosen' her up any time I suggested we should fuck. She would drink a few glasses rather quickly and would indeed become quite free in the bedroom. I found it rather uncomfortable that she would ask about my work while we were going at it. Robert's name would come up and I could swear she would moan when it did. She did seem more into blow jobs, which I certainly enjoyed. I would remember her sucking off my boss and I suspected she was thinking of the same thing. A few nights after the evening with Robert, I took Ashley out for a nice dinner, thinking I needed to make it up to her for being such a wuss. It was a nice Italian restaurant that she had wanted to go to for some time. Ashley dressed up like a knockout for the evening with a short black dress with a slit that went even higher. When we arrived at the restaurant for our later reservation the osteria was rather quiet, with only a few diners. I noticed the heads of all the staff, and the few male patrons turn when we arrived, checking out my hot wife. We ordered a nice bottle of wine, and I thought everything was going perfect until I noticed Ashley drinking too much, then becoming more and more flirty with the handsome Italian waiter as she enjoyed most of the second bottle. She started to touch his arm when he would come over to pour us more wine. The waiter started to address her as 'Bella' and should would respond every time by calling him 'mi amor'. When she got up to go to the restroom Ashley stumbled a bit and the waiter offered to help. Ashley took his arm, but he quickly moved his arm around her waist to give her support. I tried not to stare but I did notice that by the time they got near the restroom his hand was clearly on her big ass, which was shown off nicely in the tight dress. While she was in the restroom I saw our waiter talking to two other men from the restaurant staff. They kept looking at our table and it seemed clear they were gossiping about my wife. When she finally came back (the waiter again took the opportunity to cop a feel as he kindly escorted her) we got even more attention. The host came over with complimentary limoncellos, which we both drank down. Ashley smiled broadly and complimented him on how friendly and handsome the waitstaff was. The busboy who came to clear our plates made no effort to hide the fact that he was looking down my wife's cleavage even while I was sitting right there. When I finally had to go to the restroom I was a little nervous to leave her alone. I tried to hurry, mad at myself for letting my wife be in this position. When I returned it wasn't as bad as I had feared but our waiter and the host were on either side of my wife. The host hand his hand on my wife's shoulder and was looking down her dress while she talked to him. The waiter was on the other side, looking at the leg my wife was exposing, which seemed even more generous than I remembered, rising far up her thigh. I could see he had an erection forming a tent in his pants, and it was pointed towards my wife's face. Neither acknowledged me when I returned to my seat, so I asked to see the dessert menu. The host seemed to sneer at me as he left, and the waiter said he would be right back. When the waiter came back he brought a tray of desserts as they sometimes do in fancy restaurants as they describe the dishes. "The two I recommend for you Bella, are the creme de pot, and the tiarmisu." "Oh, mi amor, I don't know if I can decide." Ashley said in a girlish voice. The waiter then did something I had never seen them do in any restaurant. "Allow me to give you a sample Bella" he said as he stuck his finger in the pot de creme and proffered it to her, placing it just in front of my her mouth. Ashley seemed to take this in stride, and bent forward to lick the dessert from his finger. In fact she went back for a little more, sucking his finger slowly to make sure she got it all. "Oh, so good." she moaned. The waiter then stuck his finger into the tiramisu and placed it ahead of her. This time when she went to lick it off he pulled it away teasingly. "Oh, please?" she begged. The waiter returned his finger and this time my wife hungrily took all of his finger in her mouth. I could hear her make a sucking sound and I looked around to see if the two other occupied still occupied tables were taking notice. They weren't but several staff were enjoying the show. "Do you want it?" the waiter asked my wife with a smirk. "I do...please." Ashley pleaded. He laughed and walked away, coming back soon with a plate of tiramisu and another limoncello for her. I was never asked if I would like dessert. When we were left alone for a moment I was about to suggest we pay and leave but a very drunk Ashley was loving the dinner. "Such a nice place and great service!" she lauded as she drank down her shot, "Thank you for taking me!" Her gratitude softened me, but I still thought the evening had gone far enough. When the waiter came by again I firmly asked for the cheque and Ashley made no objection. When we got up to leave I made a move to help Ashley from her chair, but the host was faster, putting his arm around her and helping her towards the door. Ashley was very drunk now. She leaned on as he lowered his hand to her bottom. I watched as he gave it a gentle squeeze but chose not to make a scene now that we were finally going. When we got to the door I walked over to give my ticket to the valet parking attendant. The attendant stopped to ogle my wife then went off to get my car. Looking back I saw that our host was now holding my wife rather closely with his hand around her waist. He cupped her breast while she rested her head on his shoulder. As I approached I heard him asking for her number. "I...shouldn't." Ashley said with a slur, "my husband..." she looked over at me while I approached. "Just a kiss goodbye then?" he implored. I was just 30 feet away! I started to say something but Ashley spoke first. "A kiss? Well...my husband does like me to be friendly..." She emphasized the word friendly and looked right at me. My thoughts raced to her kneeling naked before my boss after I had given her permission to blow him. My face went red with anger and shame. "A goodbye kiss would be all right." she decided. The host did not hesitate, even though I was now right beside them. He dipped her head back a little and kissed her hard on the lips. I watched him explore her mouth with his tongue as his hands greedily groped her ass. Ashley gave no resistance, she simply purred as he enjoyed her. I just watched, fighting the urge to touch my growing cock. When he finally broke the kiss the restaurant host wrote down something on a piece of paper while holding her and tucked it in my wife's bra. He smacked her on the ass and looked towards me as if offering her back to me. I was about to take her when I heard an accented voice right behind me. "Bella...no kiss for me?!" The host pivoted away from me and handed my wife to our waiter. "Oh, mi amor...you also need a kiss?" my wife asked the waiter teasingly. The waiter did not answer. He pushed my wife against the wall and kissed her passionately. Ashley wrapped her arms around his neck as he pressed his body against hers. I could see him thrusting what I was sure must be a fresh erection against he slowly as she moaned. I was now fully erect myself. I knew I should stop this but the valet attendant and the bus boy were now an audience to my wife being molested and I wasn't sure how they would react to me cutting in. The waiter turned my wife so he was against the wall and her back faced us. Ashley did not break the kiss, even as he lifted her dress slowly until her thong covered ass was now presented to the four of us. The bus boy and the attendant cheered. I watched his hands grope her and was now stroking my cock through my pants, and feeling terrible about myself for doing so. Finally the waiter stopped kissing her, and she looked up at him. He handed her his phone and told her to enter her number. She did as she was told, although she was so drunk I wondered if her fumbling hands would get it right. He was then gentleman enough to escort her to my car where the valet attendant took the opportunity to feel her up before she sat down in the passenger seat. I offered no tip, but instead scurried to the driver's seat and slammed the door. I took a deep breath as I watched my wife blowing kisses to the men, then accelerated away. I drove carefully after having had a few glasses of wine and Ashley fell asleep without saying anything. As we neared our home Ashley was awakened by the sound of a text coming in. She read it with some difficulty then giggled. "It looks like your boss wants me to go on a date with him." she said tauntingly. I looked at the excitement on my beautiful wife's face and wondered again where this was all headed.