Dream Work Trip (Part 2)
Itâs Tuesday afternoon and Iâm in the middle of a meeting with a client. Last nightâs activities in my hotel room were etched in my brain and could hardly concentrate on this meeting. The fact that I wore black satin panties under my pants certainly didnât help matters. My meeting is later in the afternoon followed by an early dinner with the same clients. The cocktails I drank during our dinner start to make my mind wander to last nights events with Clayton once again. I sneak a peak at my email during the dinner and see an email from Clayton. Just seeing an unread email in my inbox from him made my cock rock hard under my panties and pants. I open the message a read âHey baby!! Landed in London. Really hope to see you again when Iâm back. Hope youâre having a great day! Claytonâ. I sneak a reply back to Clayton while at the dinner table with my clients. I tell them I have to text my wife something. I reply back to Clayton with âHi Clayton. You have no idea how horny youâve made me since we met last night. Iâm hoping we can see each other Thursday and/or this weekend before you have to head back to Texas and me to Cali. I have a sexy outfit in mind for your the next time we meet. You will not be disappointed ;)â
After hitting send, I continued with the dinner and tried to stay focused as much as possible. This was proving to be impossible. As the drinks continue and dinner winds down, I get excited to get back to the hotel and put on an outfit. The dinner finally comes to an end and we leave in our respective Ubers. My hotel is luckily close by, so with in 15 minutes of leaving that client dinner, Iâm dressed in a red teddy and an opaque black body stocking.
I go online and check my email first thing. To my delight, I see two messages from Clayton. The first has no message, but has two pics attached. One of his cock and one full pic of him fully hard. The second message said âI canât stop thinking about you. We need to meet again. I donât have any more early flights until I head back to Texas Sunday morning. Would love to stay over and have a raunchy night with my new favorite slutâ. This sends my heart racing. I take out my dildo that I purchased yesterday and lube it up and slide inside of me. I then grab my laptop and make a 5 minute video for Clayton on my back using my dildo, with my red nighty pulled up and my hard cock sticking out from my crotchless body stocking. Considering it was around 9pm in Boston, I assumed Clayton was asleep in London. I watch the video to make sure it looked ok and then send to Clayton. I donât know what possessed me to do that, as I never have made a video for a guy before, but I was so caught up in my lust, I couldnât help myself. To my surprise, about 10 min after I sent him the video, he replied back âYou are amazing!!!! Are you on Skype at all? Iâd love to chat and see you.â I reply back with my Skype address and a message. âThank god youâre up!! Iâd love to chat and I am on Skype. Here is my addressâ. I then login into Skype immediately and within seconds, I see a chat request from Clayton. Clayton and I chatted for only a couple minutes when he asked me if I cam. I told him I actually cammed with someone before he emailed me last night. This must have made Clayton super horny, because within seconds, I see the message on Skype of an incoming call.
I hit accept and see Clayton naked and smiling and saying âOh wow. Already startedâ as I get back in my position and slide my dildo in and out while we chat. He says âI stayed up hoping I could see you tonight. So glad I did. â I smiled and told him how he is all I thought about all day. Clayton then says âand that you cammed with a guy last night before we hooked up. You are one horny fucker, thatâs why youâre my favorite.â I told Clayton that I couldnât wait to see him in the flesh and have fun all night with him. I have late meetings Friday and nothing Saturday so you can stay as long as you want. He replied âcount on it. I may never leave. At this point, we begin to stroke while I continue to use my left hand to thrust my vibrating dildo in and out while I moan and slowly stroke with my right hand. Clayton and I talk dirty to each other while we stroke and stare at one another. He then says, âI need a slutty flight attendant like you.â I told him Iâd be his personal slut and would be his secret lover. That comment reinforced my costume idea, for when Clayton and I meet. Iâll be a sexy stewardess. I donât mention it to him, as we continue to talk dirty and stoke. After about a half hour, we are both dying to cum. Clayton says âare you ready to cum baby? Iâm so close.â I nod while still moaning and begin to fuck myself fast and hard the dildo, while I spread my legs and stroke faster. I then move my position in bed and slip my nyloned legs over my head as my cock points toward my mouth inches away Clayton moans âfuck yeah!!! Cum in your mouth baby!â Clayton sees me flipped upside down with my left hand continuing to fuck myself and my right hand stroking my throbbing cock until I start to shake and shoot an enormous load into my eager mouth. As I cum, I hear Clayton moan as iâm able to turn my head to see him cover his salt and pepper hairy chest with a load as large as the one I just swallowed from myself. After we both cum, we chat for another 10 minutes. He asks me if I ever fully cross dressed before and I told him I did in my teens and 20s but havenât since Iâve been married. Clayton then says âI wish we met back then, you must have looked hot and passable. Youâre still in good shape, you would for sure still pull it off, but fully understand why you still donât. I smiled and thanked him and told him I really want to and think about it a lot. After some more chit chat, we retire for the evening, as we close our laptops and fall asleep, still in my outfit.
Fast forward to Thursday. My meeting ends around 3pm and I decide to walk back to my hotel. While walking, I google costume shops in the area and lucky enough, I find an alt type costume shop just minutes from my hotel in Cambridge. I take a detour and walk over to this shop, in the hopes of finding my desired costume. After a short walk, I arrive at this shop. To my delight, this place is big and has a ton of options, so I start to look around. This was a thrift type of shop so I was able to find ton of sexy lingerie and outfits. As I look around, I glance at a rack and notice a navy blue blazer and skirt. I look closely and I notice it is a used flight attendant outfit, similar to uniform you see on a flight attendant who works for a well known, NY based carrier (not the one Clayton flys for unfortunately). I look around this rack to see what else is there and find another used outfit that was less sexy. I pull out the matching blazer and skirt and look around some more. Suddenly, I see a section that has a small selection of wigs. My heart starts to race, as I think about seriously fully cross dressing for the first time in 10 years. I look at the few wigs they had and found a shoulder length, slightly curly, black wig. This was almost identical to the one I used to wear when I was younger. I pause for a moment and think about it, but my horniess prevailed. I go over and grab the wig and continue looking around. This store, like the sex shop I had been to on Monday, was excellent. Cambridge is slowly becoming my favorite city. I walked around the store for over 20 minutes and found so many great clothes to wear, as well cool male vintage tees and albums. Eventually, I check out with 3 large bags full of clothes and a few albums to add to my collection. During my travels in this large store, I was able to find a dress similar to one I used to wear back in the day. Itâs a black long sleeve mini dress with high collar and white bow at the top. I grab that dress and also find a used cheerleader uniform from a local HS, that I bought with white sneaker and white tights. As Iâm checking out, I get nervous but as I approach the counter, Iâm met by a friendly young gay man. He smiles as he rings me up. He rings up my things and as he rings up the black mini dress last, he says âgorgeous, great choiceâ. I sheepishly smile and thank him. He then asks me if I had ever been to this club in Boston. I told him Iâm in town on business so wasnât aware of it. He told me they have a big drag show at this club on Friday nights and gave me a flyer. One of the drag queens is his roommate and was promoting his show. I smiled and politely said that I should check it out. I told him it sound great and would love to check it out, though I was thinking there is no way Iâd go there dressed. I had been to shows like this many times when I was younger, but not since I was married. I was curious but In the back of my head, I knew wouldnât go. I leave the store and lug 3 large bags into an Uber and take the short ride back to my hotel. I drop of the bags and then make a quick stop to a nearby mall to pick up a pair of black high heels, a lace matching bra and panty set, and makeup that I ordered online and a large dept store. I once again get back to the hotel after picking up my stuff at the mall. The excitement of knowing im going to fully crossdress for Clayton makes the ride up to my room seem as long as possible.
I eventually get to my room and itâs around 6pm I check my email and find a message from Clayton. It says. âHey sexy. Iâm back in town! My crew and I are having dinner at 7 but should be done around 9 and will be right overâ. I tell him I canât wait Iâll be ready for him. I immediately take a shower and begin to shave my legs and ass so Iâm totally smooth. I then go into my routine that I havenât done in 10 years. I start to apply my make up. Subtle red lipstick, mascara, and a small amount of eye shadow. I then get up and slip into my black crotchless body stocking and slide up a pair of lace panties over them. I then put on white blouse and a red satin scarf, followed by my navy blue skirt and blazer. I then put the high heels I bought. I walk around the room practicing to walk to heels again since had been so long. After a short time, my muscle memory came back and was able to seamlessly walk in heels like I used to. Finally, went to my mirror and worked on my hair and applied my medium length black wig. I looked myself in the mirror and was rock hard. I sure did miss this. By the time I finished getting ready, itâs around 8:30pm so Iâm in waiting mode. I keep an eye on my email while watching some porn. About 10 minutes later, Clayton emails me that heâs on his way. My cock jumps as I read it. I tell Clayton that I canât wait to see him. About 20 minutes later, I hear a knock at my door.
My heart starts to pound. I get up from the bed and walk over to the door and peak thru the peephole and sure enough, Clayton is standing outside. I open the door and his jaw drops and muttered âoh my god, what a pleasant surprise as he kisses me and walks into my room. Clayton takes off his coat and then comes over to me and we make out. Standing in the middle of my room and making out. He smiles and tells me âyou have no idea how hot you look, I need you on my crewâ. I smile and kiss him again. Then I begin to undress Clayton while I tell him how much Iâve thought about him since Monday night. We kiss again and then he says to me. If you worked for my crew, we would never leave each otherâs side. Iâd get hard watching you work every day. I tell him, after every flight where we have a layover, youâd be in my room every night. Iâd be your best employee. I then start to kiss Clayton and slide off his sweater and tee shirt. My lips begin to work their way down to Claytonâs neck and hairy chest as he softly moans. My eyes looking up at him the entire time as he looks down at me. Our eyes staring into one anotherâs as my lips work their way down to his mid drift as i undo his belt and lower his pants and briefs. Once his clothes are off, he has me stand and we go over to the bed.
Clayton lays on his back and smiles down at me as a kneel before him in bed. In my full uniform and heels. I look up at him and he says âyes baby, I dream about you every night when we work togetherâ. Feeling he is getting into a rolepay scenario, I enthusiastically play along. I lay down next to him kissing his chest, while I slowly stroke his hard cock. I look at Clayton and tell him that I play with myself on flights thinking about him and how much I worship him. He says â youâre so great as an employee, youâre even better right now. I smile and we make out so more while I stroke his cock slowly. I begin to kiss his hairy chest again and work my lips down to his rock hard cock. My eyes locked on Clayton, as he lays back and closes his eyes. My lips begin to kiss his thick cock head, as they lower down his hard 8 inch shaft. I slowly work my lips up and down his shaft. Clayton says âThatâs it baby. I wanted this since your first day you worked with us. Oh yes.â My lips slowly work up and down his hard cock from tip to base. My cock rock hard under my panties and skirt, fully clothed while I worship Claytonâs cock. After giving his 8 inch tool some needed attention for a good 15-20 minutes, he tells me to get up.
I climb on top of him and we start to kiss. Our lips and tongue all over one anotherâs. The kiss is long and intense. He then hugs me hard and lifts me up and puts me on my back, as Clayton is now on top of me. We kiss some more and he then gets out of bed and grabs the lube from my tv stand and pulls out a condom from his pocket. Clayton looks at me, as I lay in full flight attendant uniform and heels, as I lick my lips as is I stare back. He gets back into bed and hugs me and we make out once again, while I wrap my nyloned legs right around him. He then gets up and pulls off my skirt and lacy panties. Laying in just a navy blue blazer, white blouse, my crotchless body stocking and black heels. Clayton then grabs a hold my legs and pulls them up. He applied lube to me and slides to fingers up and in me. I leak as he fingers my prostate, driving me so wild as he stares down at me. He then puts on his condom and some lube and grabs a hold of both my heels and pulls back my legs. Clayton slides his hard 8 inch cock inside of me and let out a loud moan. He slowly slides his cock in and out as we both moan. Clayton then says âIâm going to fuck you every day at work. All over the planeâ. I look up at him and say âanywhere any time you want. I promise sir.â Clayton starts to pick up the pace, sliding his cock all the way in and out. He starts fucking more aggressively and says sternly âevery time I take a bathroom break on flights, I want you bent over and ready for me, understand?â I moan yes sir loudly as he says âgood girlâ. Our eyes stay locked as he continues to grip my heels and spread my legs as he fuck my wet hole. Yelling down at me âyour my work wife, baby, I fucking love fucking youâ. I moan back how no cock has ever felt better inside of me than yours. He then yells your going to make me cum and I yell yes baby. Please cum. Fuck me sir! Fuck me! Clayton then tells me that he is cumming and we kiss. He keeps his cock buried deep as we make out. He then whispers to me âyou are so fucking hotâ
Clayton rolls off of me and pulls me toward him as we laid together after our intense session. We casually chat for the next hour. Everything from music, sports, movies, then eventually, or past experiences, while Iâm curled up on his hairy chest in just my body stocking. As we started to talk about our experiences with men, our motors started to get going again. He tells me stories of past hookups on trip and in Boston when he stays one week a month. He has some buds heâs still keeps in touch with in the area. I share some experiences from my time in London, when I interned for a firm for 3 months after college and was dressed up every night in soho. Clayton tells me that Iâm still passable to him now so must have been really passable then. I smile and kiss his chest, as I lay on him and we continue chatting He then says that he and bud of his go to this drag bar in Boston. His says the name of the club and itâs the same one that the clerk at the store told me earlier, where his roommate is performing. I tell Clayton of that interaction and he says. âIâd love to go with you tomorrow night. You think you might want to?â I look up at him and smile and nod my head. Clayton says âyea, thatâs great. Iâll call my bud who lives nearby and he can meet us there. We will have a blast. Iâm scared by excited.
We start to kiss after this exchange. Leaning over him and making out while he lays back. This continues for a while before he gets up from bed and gets back in as I lay back and he gets back on top of me again. We make out while I feel his now hard bare cock rubbing against me. He then looks at me and I just smile and nod. I know what Clayton wants. He immediately slides his bare cock inside of me and fucks me in missionary position once again. My legs spread, as his bare cock slides in and out of me. He then tells me to stand up. Clayton asks me to bend over the bed while he gets behind me. I assume the position and feel his hands on my nyloned hips, as he thrusts his 8inch cock back into me. Clayton is fucking me hard as he stands behind me and I kneel over the bed. Spanking my ass, as he fucks me. This goes on for a long time. Clayton then tells me to get up and I turn and kiss him. Clayton picks me up as I wrap my nylon legs around him. His strong arms around me in his lap as he pins me against the hotel wall. He starts kissing me while he pounds me against the wall. Fucking with so much passion. After a little while of this, he lets me down and has me bend over in bed. We get back into bed and burry my head in my pillow, as Clayton thrusts his cock in and out of me. Both of us moaning loudly. He eventually starts fucking me hard and tells me to get ready. He then pulls out of me and I feel as a warm sensation, as he jerks his cock and shoots his cum on my hole. After he cums, Clayton slides his cock inside of me again, to give a bit of his cum that was on my hole. It felt amazing. I turn around and we kiss again. Once again, he holds me in his arms as we chat some more. We eventually fall asleep, as itâs around 1am into Friday morning. At around 5am, I woke up to feel Clayton kissing my body. I wake up and smile. We begin to make out. Another session is about to start. A perfect way to start a Friday, one which will ultimately be one of my hottest days ever. To be continuedâŚ..
After hitting send, I continued with the dinner and tried to stay focused as much as possible. This was proving to be impossible. As the drinks continue and dinner winds down, I get excited to get back to the hotel and put on an outfit. The dinner finally comes to an end and we leave in our respective Ubers. My hotel is luckily close by, so with in 15 minutes of leaving that client dinner, Iâm dressed in a red teddy and an opaque black body stocking.
I go online and check my email first thing. To my delight, I see two messages from Clayton. The first has no message, but has two pics attached. One of his cock and one full pic of him fully hard. The second message said âI canât stop thinking about you. We need to meet again. I donât have any more early flights until I head back to Texas Sunday morning. Would love to stay over and have a raunchy night with my new favorite slutâ. This sends my heart racing. I take out my dildo that I purchased yesterday and lube it up and slide inside of me. I then grab my laptop and make a 5 minute video for Clayton on my back using my dildo, with my red nighty pulled up and my hard cock sticking out from my crotchless body stocking. Considering it was around 9pm in Boston, I assumed Clayton was asleep in London. I watch the video to make sure it looked ok and then send to Clayton. I donât know what possessed me to do that, as I never have made a video for a guy before, but I was so caught up in my lust, I couldnât help myself. To my surprise, about 10 min after I sent him the video, he replied back âYou are amazing!!!! Are you on Skype at all? Iâd love to chat and see you.â I reply back with my Skype address and a message. âThank god youâre up!! Iâd love to chat and I am on Skype. Here is my addressâ. I then login into Skype immediately and within seconds, I see a chat request from Clayton. Clayton and I chatted for only a couple minutes when he asked me if I cam. I told him I actually cammed with someone before he emailed me last night. This must have made Clayton super horny, because within seconds, I see the message on Skype of an incoming call.
I hit accept and see Clayton naked and smiling and saying âOh wow. Already startedâ as I get back in my position and slide my dildo in and out while we chat. He says âI stayed up hoping I could see you tonight. So glad I did. â I smiled and told him how he is all I thought about all day. Clayton then says âand that you cammed with a guy last night before we hooked up. You are one horny fucker, thatâs why youâre my favorite.â I told Clayton that I couldnât wait to see him in the flesh and have fun all night with him. I have late meetings Friday and nothing Saturday so you can stay as long as you want. He replied âcount on it. I may never leave. At this point, we begin to stroke while I continue to use my left hand to thrust my vibrating dildo in and out while I moan and slowly stroke with my right hand. Clayton and I talk dirty to each other while we stroke and stare at one another. He then says, âI need a slutty flight attendant like you.â I told him Iâd be his personal slut and would be his secret lover. That comment reinforced my costume idea, for when Clayton and I meet. Iâll be a sexy stewardess. I donât mention it to him, as we continue to talk dirty and stoke. After about a half hour, we are both dying to cum. Clayton says âare you ready to cum baby? Iâm so close.â I nod while still moaning and begin to fuck myself fast and hard the dildo, while I spread my legs and stroke faster. I then move my position in bed and slip my nyloned legs over my head as my cock points toward my mouth inches away Clayton moans âfuck yeah!!! Cum in your mouth baby!â Clayton sees me flipped upside down with my left hand continuing to fuck myself and my right hand stroking my throbbing cock until I start to shake and shoot an enormous load into my eager mouth. As I cum, I hear Clayton moan as iâm able to turn my head to see him cover his salt and pepper hairy chest with a load as large as the one I just swallowed from myself. After we both cum, we chat for another 10 minutes. He asks me if I ever fully cross dressed before and I told him I did in my teens and 20s but havenât since Iâve been married. Clayton then says âI wish we met back then, you must have looked hot and passable. Youâre still in good shape, you would for sure still pull it off, but fully understand why you still donât. I smiled and thanked him and told him I really want to and think about it a lot. After some more chit chat, we retire for the evening, as we close our laptops and fall asleep, still in my outfit.
Fast forward to Thursday. My meeting ends around 3pm and I decide to walk back to my hotel. While walking, I google costume shops in the area and lucky enough, I find an alt type costume shop just minutes from my hotel in Cambridge. I take a detour and walk over to this shop, in the hopes of finding my desired costume. After a short walk, I arrive at this shop. To my delight, this place is big and has a ton of options, so I start to look around. This was a thrift type of shop so I was able to find ton of sexy lingerie and outfits. As I look around, I glance at a rack and notice a navy blue blazer and skirt. I look closely and I notice it is a used flight attendant outfit, similar to uniform you see on a flight attendant who works for a well known, NY based carrier (not the one Clayton flys for unfortunately). I look around this rack to see what else is there and find another used outfit that was less sexy. I pull out the matching blazer and skirt and look around some more. Suddenly, I see a section that has a small selection of wigs. My heart starts to race, as I think about seriously fully cross dressing for the first time in 10 years. I look at the few wigs they had and found a shoulder length, slightly curly, black wig. This was almost identical to the one I used to wear when I was younger. I pause for a moment and think about it, but my horniess prevailed. I go over and grab the wig and continue looking around. This store, like the sex shop I had been to on Monday, was excellent. Cambridge is slowly becoming my favorite city. I walked around the store for over 20 minutes and found so many great clothes to wear, as well cool male vintage tees and albums. Eventually, I check out with 3 large bags full of clothes and a few albums to add to my collection. During my travels in this large store, I was able to find a dress similar to one I used to wear back in the day. Itâs a black long sleeve mini dress with high collar and white bow at the top. I grab that dress and also find a used cheerleader uniform from a local HS, that I bought with white sneaker and white tights. As Iâm checking out, I get nervous but as I approach the counter, Iâm met by a friendly young gay man. He smiles as he rings me up. He rings up my things and as he rings up the black mini dress last, he says âgorgeous, great choiceâ. I sheepishly smile and thank him. He then asks me if I had ever been to this club in Boston. I told him Iâm in town on business so wasnât aware of it. He told me they have a big drag show at this club on Friday nights and gave me a flyer. One of the drag queens is his roommate and was promoting his show. I smiled and politely said that I should check it out. I told him it sound great and would love to check it out, though I was thinking there is no way Iâd go there dressed. I had been to shows like this many times when I was younger, but not since I was married. I was curious but In the back of my head, I knew wouldnât go. I leave the store and lug 3 large bags into an Uber and take the short ride back to my hotel. I drop of the bags and then make a quick stop to a nearby mall to pick up a pair of black high heels, a lace matching bra and panty set, and makeup that I ordered online and a large dept store. I once again get back to the hotel after picking up my stuff at the mall. The excitement of knowing im going to fully crossdress for Clayton makes the ride up to my room seem as long as possible.
I eventually get to my room and itâs around 6pm I check my email and find a message from Clayton. It says. âHey sexy. Iâm back in town! My crew and I are having dinner at 7 but should be done around 9 and will be right overâ. I tell him I canât wait Iâll be ready for him. I immediately take a shower and begin to shave my legs and ass so Iâm totally smooth. I then go into my routine that I havenât done in 10 years. I start to apply my make up. Subtle red lipstick, mascara, and a small amount of eye shadow. I then get up and slip into my black crotchless body stocking and slide up a pair of lace panties over them. I then put on white blouse and a red satin scarf, followed by my navy blue skirt and blazer. I then put the high heels I bought. I walk around the room practicing to walk to heels again since had been so long. After a short time, my muscle memory came back and was able to seamlessly walk in heels like I used to. Finally, went to my mirror and worked on my hair and applied my medium length black wig. I looked myself in the mirror and was rock hard. I sure did miss this. By the time I finished getting ready, itâs around 8:30pm so Iâm in waiting mode. I keep an eye on my email while watching some porn. About 10 minutes later, Clayton emails me that heâs on his way. My cock jumps as I read it. I tell Clayton that I canât wait to see him. About 20 minutes later, I hear a knock at my door.
My heart starts to pound. I get up from the bed and walk over to the door and peak thru the peephole and sure enough, Clayton is standing outside. I open the door and his jaw drops and muttered âoh my god, what a pleasant surprise as he kisses me and walks into my room. Clayton takes off his coat and then comes over to me and we make out. Standing in the middle of my room and making out. He smiles and tells me âyou have no idea how hot you look, I need you on my crewâ. I smile and kiss him again. Then I begin to undress Clayton while I tell him how much Iâve thought about him since Monday night. We kiss again and then he says to me. If you worked for my crew, we would never leave each otherâs side. Iâd get hard watching you work every day. I tell him, after every flight where we have a layover, youâd be in my room every night. Iâd be your best employee. I then start to kiss Clayton and slide off his sweater and tee shirt. My lips begin to work their way down to Claytonâs neck and hairy chest as he softly moans. My eyes looking up at him the entire time as he looks down at me. Our eyes staring into one anotherâs as my lips work their way down to his mid drift as i undo his belt and lower his pants and briefs. Once his clothes are off, he has me stand and we go over to the bed.
Clayton lays on his back and smiles down at me as a kneel before him in bed. In my full uniform and heels. I look up at him and he says âyes baby, I dream about you every night when we work togetherâ. Feeling he is getting into a rolepay scenario, I enthusiastically play along. I lay down next to him kissing his chest, while I slowly stroke his hard cock. I look at Clayton and tell him that I play with myself on flights thinking about him and how much I worship him. He says â youâre so great as an employee, youâre even better right now. I smile and we make out so more while I stroke his cock slowly. I begin to kiss his hairy chest again and work my lips down to his rock hard cock. My eyes locked on Clayton, as he lays back and closes his eyes. My lips begin to kiss his thick cock head, as they lower down his hard 8 inch shaft. I slowly work my lips up and down his shaft. Clayton says âThatâs it baby. I wanted this since your first day you worked with us. Oh yes.â My lips slowly work up and down his hard cock from tip to base. My cock rock hard under my panties and skirt, fully clothed while I worship Claytonâs cock. After giving his 8 inch tool some needed attention for a good 15-20 minutes, he tells me to get up.
I climb on top of him and we start to kiss. Our lips and tongue all over one anotherâs. The kiss is long and intense. He then hugs me hard and lifts me up and puts me on my back, as Clayton is now on top of me. We kiss some more and he then gets out of bed and grabs the lube from my tv stand and pulls out a condom from his pocket. Clayton looks at me, as I lay in full flight attendant uniform and heels, as I lick my lips as is I stare back. He gets back into bed and hugs me and we make out once again, while I wrap my nyloned legs right around him. He then gets up and pulls off my skirt and lacy panties. Laying in just a navy blue blazer, white blouse, my crotchless body stocking and black heels. Clayton then grabs a hold my legs and pulls them up. He applied lube to me and slides to fingers up and in me. I leak as he fingers my prostate, driving me so wild as he stares down at me. He then puts on his condom and some lube and grabs a hold of both my heels and pulls back my legs. Clayton slides his hard 8 inch cock inside of me and let out a loud moan. He slowly slides his cock in and out as we both moan. Clayton then says âIâm going to fuck you every day at work. All over the planeâ. I look up at him and say âanywhere any time you want. I promise sir.â Clayton starts to pick up the pace, sliding his cock all the way in and out. He starts fucking more aggressively and says sternly âevery time I take a bathroom break on flights, I want you bent over and ready for me, understand?â I moan yes sir loudly as he says âgood girlâ. Our eyes stay locked as he continues to grip my heels and spread my legs as he fuck my wet hole. Yelling down at me âyour my work wife, baby, I fucking love fucking youâ. I moan back how no cock has ever felt better inside of me than yours. He then yells your going to make me cum and I yell yes baby. Please cum. Fuck me sir! Fuck me! Clayton then tells me that he is cumming and we kiss. He keeps his cock buried deep as we make out. He then whispers to me âyou are so fucking hotâ
Clayton rolls off of me and pulls me toward him as we laid together after our intense session. We casually chat for the next hour. Everything from music, sports, movies, then eventually, or past experiences, while Iâm curled up on his hairy chest in just my body stocking. As we started to talk about our experiences with men, our motors started to get going again. He tells me stories of past hookups on trip and in Boston when he stays one week a month. He has some buds heâs still keeps in touch with in the area. I share some experiences from my time in London, when I interned for a firm for 3 months after college and was dressed up every night in soho. Clayton tells me that Iâm still passable to him now so must have been really passable then. I smile and kiss his chest, as I lay on him and we continue chatting He then says that he and bud of his go to this drag bar in Boston. His says the name of the club and itâs the same one that the clerk at the store told me earlier, where his roommate is performing. I tell Clayton of that interaction and he says. âIâd love to go with you tomorrow night. You think you might want to?â I look up at him and smile and nod my head. Clayton says âyea, thatâs great. Iâll call my bud who lives nearby and he can meet us there. We will have a blast. Iâm scared by excited.
We start to kiss after this exchange. Leaning over him and making out while he lays back. This continues for a while before he gets up from bed and gets back in as I lay back and he gets back on top of me again. We make out while I feel his now hard bare cock rubbing against me. He then looks at me and I just smile and nod. I know what Clayton wants. He immediately slides his bare cock inside of me and fucks me in missionary position once again. My legs spread, as his bare cock slides in and out of me. He then tells me to stand up. Clayton asks me to bend over the bed while he gets behind me. I assume the position and feel his hands on my nyloned hips, as he thrusts his 8inch cock back into me. Clayton is fucking me hard as he stands behind me and I kneel over the bed. Spanking my ass, as he fucks me. This goes on for a long time. Clayton then tells me to get up and I turn and kiss him. Clayton picks me up as I wrap my nylon legs around him. His strong arms around me in his lap as he pins me against the hotel wall. He starts kissing me while he pounds me against the wall. Fucking with so much passion. After a little while of this, he lets me down and has me bend over in bed. We get back into bed and burry my head in my pillow, as Clayton thrusts his cock in and out of me. Both of us moaning loudly. He eventually starts fucking me hard and tells me to get ready. He then pulls out of me and I feel as a warm sensation, as he jerks his cock and shoots his cum on my hole. After he cums, Clayton slides his cock inside of me again, to give a bit of his cum that was on my hole. It felt amazing. I turn around and we kiss again. Once again, he holds me in his arms as we chat some more. We eventually fall asleep, as itâs around 1am into Friday morning. At around 5am, I woke up to feel Clayton kissing my body. I wake up and smile. We begin to make out. Another session is about to start. A perfect way to start a Friday, one which will ultimately be one of my hottest days ever. To be continuedâŚ..
2 years ago
