The Dream work trip
2014 had started off extremely well. I spent the first week of the new year on vacation in sunny and warm Mexico, with my wife. It was a week of drinking, eating, and relaxing. I was enjoying every second and didn’t want the trip to end. This is mostly due to the fact that after great Mexican vacation, I also knew that on Monday morning, the day after we get back, I was due to fly out to visit a client for 9 days in Boston. Going from sunny Mexico to the frigid northeast was not ideal. I was dreading everything about the trip. The 5:30am flight time on Monday didn’t help either. After we return from our vacation, I begin to unpack my luggage and replace my vacation clothes with professional attire and for my work trip the following morning. I wake up early and kiss my wife goodbye and leave for the airport. I arrive back at the airport once again and was fortunate enough to upgrade my seat for the long 6 hour flight out. I get on the plane r fall right asleep and was able to sleep the entire 6 hours of my flight. I awake to the voice of our pilot telling us we’re about to land. We land around 2:30pm and I exit the plane and am immediately hit by the harsh cold air. This is not good. I wait for my luggage. I see and grab my bag and go to the curb and grab the first cab I see. My ride lasts about 20 minutes before I arrive at my hotel in Cambridge, just outside of Boston. The hotel is a high rise and I check in and go to the 18th floor to my room.
My room is pretty nice. Normal room but a great, high view of Boston. I unpack and then check in with my wife and let her know I landed. I follow that call with a call to my client, who I’m due to visit for my nine day due diligence visit. Because of schedule conflicts, and find out that my client can’t meet until the next day at 3pm. I was angry that I rushed to get there, just to have to wait another day before we even meet. I could have stayed home one more day. However, I had to accept that this situation will not change, so might as well make the most of the trip. After my client call, I take out my laptop and strip naked and lay in bed. Time to have some solo fun. I go to my favorites folder and find a great movie with a muscular bear and a young crossdresser. My cock gets hard immediately and begin to slowly stroke. I plan to edge for a couple of hours and have some fun while I’m alone and have nothing to do. As I lay and stroke while I stare at my laptop, I get more and more horny by the second.
About an hour into edging, my mind starts to wander. As I watch this hot CD and gorgeous bear go at it on my laptop screen, I begin to wish I had some clothes to wear. I used to fully crossdress quite a bit starting from 19 and thru my 20s. Once I met my wife, I stopped fully dressing, but would still wear panties, pantyhose/stockings, and lingerie whenever I could when she was away. I then google adult stores in the area. I find a nice little shop near in Cambridge that had clothes and toys. After doing some more research, I call an Uber to meet me at my hotel and bring me to the store I found. Once the Uber picks me up, I hop out and enter the store. I walk down the stairs and see a small room with a ton of outfits, gear, and sex toys. This place is amazing. I grab 3 bra and panty sets, a res silk nighty, a school girl grey skirt with white garter belt and white opaque stockings, a black crotchless body stocking, and tan thigh highs. I also grab an 8 inch flesh colored vibrating dildo, AAA batteries, and some water based lube. The woman who rung me up seemed quite amused by everything I was buying, but I was still very horny and couldn’t wait to check out and head back to my room. I call another uber as I check out. The nice sales lady let me wait downstairs while I waited for my Uber. After a few minutes of idol chitchat, my Uber arrives. I thank the lady once again, head upstairs and hop in my Uber. We get back and I grab my big bag of goodies and head right to my room when I’m dropped off. That elevator ride seemed like the longest ever.
Once I enter the room, I strip back down again and slip on the black crotchless body stocking and red satin nighty. I grab a towel and pull out the dildo, lube, and batteries that I just purchased, and get on my bed. I flip open my laptop and continue the movie I was watching before I left earlier. The video begins from the beginning as I stroke and load my dildo with batteries. The dildo starts to vibrate after I enter the batteries and then apply lube to my new toy and smooth ass. I lean back against the headboard of my hotel bed and I slowly thrust my 8 inch vibrating dildo all the way in and out of me, while I slowly stroke my rock hard and leaking cock. The sensation makes me start to moan immediately. Feeling those dildo sliding in and out, as I continue to watch this hot, muscular bear fuck a hot your CD in missionary position drives me into a frenzy. I begin to pick up the pace as I grow more and more horny. I then lower myself and turn around and lay back and reposition my laptop. While I lay back, I raise my nyloned legs above the headboard. I’m at the point where I know I’m going to cum soon. The sensation of my dildo becomes more and more overwhelming. I turn up the vibration all the way and begin to fuck my self hard and fast. I don’t touch my cock as it sticks straight out of my crotchless body stocking and leaks precum. I’m moaning while I watch this hot CD dangle her legs over this studs shoulders and moan. After he came on the video, I couldn’t hold back any longer. The sensation grows and I begin to squirm and shake and have a massive full body orgasm. Cum shoots out of my cock and onto my body stocking and nighty, as I moan and shake on my bed. This was one of the most intense and longest orgams I’ve had in a long time. A nice and numb feeling comes over me post cum and I just lay back in bed with legs on the headboard for a good ten minutes after my explosive orgasm. I eventually compose myself and get up from my bed. After cleaning up, I slip on a black hoodie and jeans over my nighty and body stocking, and decide to head down stairs to hotel bar for a drink or two.
My mood was very laid back, as I sat at the hotel bar and ordered a drink. It was a Monday night in January and around 6pm. The bar was dead and was due to close early at 8pm. There was only woman working the bar and the booths in the bars area. . She a cute brunette in her early 20s, petite and fit. She was in a black collared shirt, black skirt, and black tights, while in white sneakers. I couldn’t keep my eyes off her. She was young and gorgeous and was constantly looking at her legs whenever she got out from behind the bar. I order another drink and get horny once again. The bartender/server and I chit chat when she has down time. Nothing special since our chats were short, as she was the only one working. At the bar by myself, I curiously look at who else is there. I see a couple in their 40s. The husband was attractive and bulky. He was bald and had a salt and pepper goatee. Sort of similar to the man in the porn video I had just watched. He never looked over thankfully as the rest of the time at the bar was spent either checking out him or the bartender. My cock begins to grow under my jeans and the feeling of nylon against my body feels much better as I stare at the bartenders nyloned legs, as she walks from behind the bar to clean up my stud’s table. At around 7:30, the bartender is all who is left. She tells me it’s last call. I order a drink and bring it up to my room with me. She says I could order two since I’m staying at the hotel, so I grab two vodka tonics, and sign my bill. I say goodbye to the bartender and get one last glance at her before I take my two drinks and head to my room. I ride up the elevator to the 18th floor and enter to my room.
As shut the door behind me and I place my two drinks down and take off my hoodie and pants. I turn on my laptop again and go back to my favorites folder, and find a favorite of mine. It’s a hotel orgy of all bears. Eight dream men going at it. I lay in my nighty and body stocking on my side, as I watch this video and sip my drink. Slowly rubbing myself, as I watch men sucking, rimming, and fucking one another. This is an hour plus video, so I can take my time. After I finish my drink, I hit pause and get off my bed and head to my new bag of goodies I purchased earlier in the afternoon. I pull out a matching cotton white bra, panties and white garter. I slide off my cum soaked body stocking and nighty and put on my bra and panties and pull up my white lace garter belt. I then pull out a pair of white opaque stockings and slide them on one by one and attach both to the garter. I finally grab the grey mini skirt and slide it up. In my new outfit, I get back in bed and start the video. I lean over and grab the dildo and lube again, that I had left on the bed. I apply lube to my hole and toy once again and turn on the dildo to medium vibrate and slide it in me all the way. I keep my dildo deep in me and then slide on my white cotton panties, to keep the dildo in place. The video continues and I grow rock hard again. Laying in a new outfit and feeling the sensation of the dildo vibrating inside of me. I quickly get up and grab my second drink and get back in bed. Watching this video and feeling more buzzed, my mind starts to wander once more.
My horniness starts to get the best of me and I open up a new tab on my browser and head to a Craigslist like personals site, that I have used for time to time. I had a good amount of experience with men when I was younger and single but not as much since I met my now wife, outside of a few one offs when I traveled other times or the wife was away and could have company. I go to the “guys for guys” section and stroll through the ads. I then see an ad that caught my eye.
“Horny married pilot. 55yo mwm 6’3 240 hairy 8cut short grey hair. I’m a top and looking my for a hot fun bottom. No one line responses and pic on first email. Fem, CD a plus. Let’s have some fun.”
I was intrigued since he has the exact type of body I’m most attracted to and he’s also married. More importantly, I was dressed and I knew it was something he’d be into. I put down my drink and took a sexy pic of myself on my laptop. I’m laying on my side smiling, with my rock hard cock noticeable under my panties. I pause for a second and compose my reply.
“Hi. I’m Steve, mwm as well. I’m 36yo 5’9 6cut handsome, dark hair, brown eyes. I’m alone in a hotel in Cambridge if you’re interested in chatting more. Am available all night. Hope to hear from you :) “
I hit send and then head back to my drink and video. His ad was posted a half hour before I replied so hoping he is real and didn’t find anyone. I continue to lay with dildo vibrating deep inside of me, under my panties, as I rub my pantied cock and sip my second drink. I keep going from the video, to my email inbox and spam folder to check for a reply. Nothing so far. I’m now 40 minutes into the video and 30 since I replied, and still nothing. As I watch the video, I notice I have a site message. I go to check and see it a friend I had chatted with many times on here and says “Hi baby”. I reply back and we get into our usual chitchat. He is married and in his early 40s and loves guys who dress up. He also loves roleplay chat and we often go to meet on Skype and occasional cam when we can. I chat with him while I watch the video, and monitor my inbox. About 30 minutes into our chat, he tells me his wife fell asleep and he is heading to his basement office. We agree to meet over on Skype and continue our chat. I send him the pic I had sent to the pilot earlier. He loved it and we started into a hot teacher/student role play. The chat is hot and intense. About another 30 minutes in on Skype, our roleplay winds down to the end and he asks me if we can cam. I say “of course baby” and I lean back in bed and position my laptop in front of me. Before my friend calls, I check my inbox once again and still nothing from the pilot. At this point, I assume he is a fake or he found someone. When I see the income call icon appear on my screen, I move on and focus on my friend. He is laying back on his chair completely naked and smiling at me and says “oh my god babe. I love your outfit”. I smile and thank him as he strokes his hard cock. I slowly slide down my white cotton panties and lay with my stockinged legs spread with my dildo deep in me. I start to fuck myself with my dildo and stroke my hard cock. As we stroke harder, he goes “cum in your mouth like you did last time.” I then flip my legs over my body as my face is inches away from my cock. I had did this the last time we cammed together so was happy to oblige. My friend watched me stroke and fuck myself hard and upside down while he strokes faster. I then start to moan loud and shake and shoot another huge load into my open mouth, while my bud closes his eyes and starts to cum on his hairy chest. I get back in normal position and we both chat and say how hot that was before signing off. It was another amazing orgasm. Out of curiosity, I check my inbox again after we log out of Skype and still nothing. I get out of bed and brush my teeth and wash my face. It’s now almost 10:30pm and no reply, so I plan to finish what’s left of my second drink and head to bed. I’m still in my outfit, as I plan to wear to bed minus the skirt. I pickup my cell phone and answer a couple of texts and then I check my inbox one last time. This time, I see a reply. I get nervous and excited right away. I had just cum but was intrigued and open the email. He says. “So hot Steve. Im Clayton, nice to meet you. Are you still looking? Let me know. I can host here at my place or travel. Here is a pic of me.” I looked at his pic and my mood changed quickly. He was tall, muscular, hairy with grey hair all over his body. He also had really nice hair and handsome. I couldn’t keep my eyes off the picture. I downed the rest of my drink and hit reply. I told him how much I liked his picture and can host him. I tell him I’m in Cambridge. He replied quickly and says his place is only 10 minutes from there. I tell him the hotel and my room # on the 18th floor. He replies back. “Yes!!!!! I will be there soon Steve.” I’m nervous and excited. I stand up and fix myself in the mirror. I pace nervously in the room as I wait. I eventually get back in bed and begin to rub myself as I wait. About 20 minutes after the pilot’s reply, the hotel phone rings.
I nervously pick up the phone. I hear a woman’s voice tell me that she is at front desk and there is a Clayton there to see me. I tell her I’ve been waiting for him and to send him up. She apologizes and says they have to check room keys after 10pm. I say no problem and I hang up. I get up from bed and walk to the door. The elevator is diagonal from my room. As I hear from my room the elevator floor stop at my floor, I open up the my room door. I see Clayton come out of elevator. Once I know it’s him, I whisper “hey” As looks for what direction to go. He then looks over and sees me in my outfit at my door. Clayton smiles and comes into my room and I close the door behind me. Clayton says “what a sexy surprise. You’re so hot Steve!” I smile as Clayton comes over and hugs me and then leans down to kiss me. We make out standing in my room, his strong hands all over my body. We share a long sensual kiss while we stand and rub on another. I then begin to kneel before Clayton and undo his belt and unzip his black pants. I pull down his pants and help him out of his shoes, while Clayton takes off his coat and unbuttons his light blue dress shirt. Clayton is now in black socks and his white briefs. I look up at him and tease his rock hard cock thru his briefs. Clayton let’s our a moan and closes his eyes. I lower his briefs to the floor and look up at him and smiles as me smiles back at me. I then open my mouth and massage his beautiful 8 inch cut cock with my lips. My cock begins to get hard a third time as I kneel before Clayton and work my lips back and forth while I look up at him, his eyes closed and moaning. He begins to rub my head and look down at me as I maintain eye contact and suck his big hard cock. After a good ten minutes enjoying Clayton’s big cock, he pulls me up and tells me to get in bed and bend over. I stand up and go the bed. I bury my head in a pillow near the headboard. Clayton reaches down and pulls out a condom from his pants pocket. He asks me if I have lube and point to the floor. He sees my dildo “wow baby, you’re in slut mode tonight”. He grabs the lube and gets in bed. My pantied pass in the air, as I feel Clayton’s presence behind me. I feel the stumble of his face as he plants his tongue into my wet hole. My cock is rock hard and pointing toward the bed. Clayton slides his tongue in me and flicks it back and forth and in and out, while he strokes my cock. I’m loving this and am making loud muffled moans while he strokes and tongue fucks me. I’m back in a frenzy for a third time since I landed 10 hours ago. My cock starts to swell in his hand and the feeling of tongue inside of me for so long was too much to take. I begin to shake and moan and shoot my third load of the night onto my bed. Clayton moans “oh yeah baby! Fucking hot!” as I shoot my load all over my bed beneath me. Clayton then pulls his tongue out of me and says “stay like that”. I hear the noise of Clayton ripping open the condom wrapper and putting it on his hard cock. He applies lube to his cock and slides it in. I pick my head up and turn to Clayton and tell him how hot he is and how good he feels in me. He starts to pound me from behind and he pulls my head back as I look back at him and kisses me, while his 8 inch cock effortlessly slid in and out of my eager hole. Clayton was the perfect man. Strong, attractive, hairy and a big cock. I’m in heaven. The room is filled with the sounds of our moans and the headboard slamming against the wall. After a little while, Clayton points to the table against the window in the corner of my room and says “go lay on that table baby”. I stand up and go over and remove the lamp and my drink glasses from the table. I lean back and bend my legs behind me as Clayton approaches the table. While standing, Clayton slides his cock into me, while I look up at him and moan. My nyloned feet pressed against the window behind me. Clayton aggressively fucks me on my table. He leans down as he gets closer and we kiss. I wrap my legs tightly around him as Clayton kisses me deeply and pounds me while I lay on my table and he stands. He then grabs by ankles and spreads me as wide as possible and fucks me fast. Both of us yelling as he tells me he’s going to cum. Clayton then keeps his cock buried deep and kisses me while he cums, as I wrap my legs around him. He then gets off of me and pulls out. He rolls off his cum filled condom and throws it into my trash, as I get up and get us towels from my bathroom. Clayton began to tell me how he has a lot of “trysts” like this in Boston when he has to stay here one week a month. He is from Texas but has to stay in Boston with his crew. Clayton asks me when I’m leaving and told him it was my first night in town and here for anther 8 days. His eyes lit up. Clayton then says. “I have to leave now because I need to meet my crew at 4am at our hotel. I’ll be in London for next two days but I’ll be back in Boston Thursday to Saturday night before I head back To Texas. I’d love to meet again.” I smile and tell him I’ll love that. We hug and make out before Clayton finishes getting dressed, and calls an Uber. Clayton says “I’ll look for you on email while I’m in London and we can chat more. I’d really love to see you again in another sexy outfit. Your body looks amazing dressed up like this.” Clayton then says goodbye and leaves. I lean back and smile. While still in my outfit, I turn off the lights and fall asleep.
I wake up the next morning and find an email from Clayton in my inbox. It says “Hi Steve. Wanted to thank you again for having me over. I want to see more of you. I wish your were one of my flight attendants. Lol. Let’s chat tonight if your free. I’ll be alone in my hotel thinking of you.” I reply, “I can’t wait to see you again. I already know what to wear for you next :). Will chat with you tonight. Xoxo Steve”. I got hard as I read Clayton’s email and began to jerk off once again in bed. I flipped myself over again and gave my self a mouthful of cum. My forth intense orgasm since I arrived. I laid down for a while before I got up to shower, grab lunch, and get ready for my meeting at 3pm. My mind was racing, knowing I’ll se Clayton again. To be continued….
My room is pretty nice. Normal room but a great, high view of Boston. I unpack and then check in with my wife and let her know I landed. I follow that call with a call to my client, who I’m due to visit for my nine day due diligence visit. Because of schedule conflicts, and find out that my client can’t meet until the next day at 3pm. I was angry that I rushed to get there, just to have to wait another day before we even meet. I could have stayed home one more day. However, I had to accept that this situation will not change, so might as well make the most of the trip. After my client call, I take out my laptop and strip naked and lay in bed. Time to have some solo fun. I go to my favorites folder and find a great movie with a muscular bear and a young crossdresser. My cock gets hard immediately and begin to slowly stroke. I plan to edge for a couple of hours and have some fun while I’m alone and have nothing to do. As I lay and stroke while I stare at my laptop, I get more and more horny by the second.
About an hour into edging, my mind starts to wander. As I watch this hot CD and gorgeous bear go at it on my laptop screen, I begin to wish I had some clothes to wear. I used to fully crossdress quite a bit starting from 19 and thru my 20s. Once I met my wife, I stopped fully dressing, but would still wear panties, pantyhose/stockings, and lingerie whenever I could when she was away. I then google adult stores in the area. I find a nice little shop near in Cambridge that had clothes and toys. After doing some more research, I call an Uber to meet me at my hotel and bring me to the store I found. Once the Uber picks me up, I hop out and enter the store. I walk down the stairs and see a small room with a ton of outfits, gear, and sex toys. This place is amazing. I grab 3 bra and panty sets, a res silk nighty, a school girl grey skirt with white garter belt and white opaque stockings, a black crotchless body stocking, and tan thigh highs. I also grab an 8 inch flesh colored vibrating dildo, AAA batteries, and some water based lube. The woman who rung me up seemed quite amused by everything I was buying, but I was still very horny and couldn’t wait to check out and head back to my room. I call another uber as I check out. The nice sales lady let me wait downstairs while I waited for my Uber. After a few minutes of idol chitchat, my Uber arrives. I thank the lady once again, head upstairs and hop in my Uber. We get back and I grab my big bag of goodies and head right to my room when I’m dropped off. That elevator ride seemed like the longest ever.
Once I enter the room, I strip back down again and slip on the black crotchless body stocking and red satin nighty. I grab a towel and pull out the dildo, lube, and batteries that I just purchased, and get on my bed. I flip open my laptop and continue the movie I was watching before I left earlier. The video begins from the beginning as I stroke and load my dildo with batteries. The dildo starts to vibrate after I enter the batteries and then apply lube to my new toy and smooth ass. I lean back against the headboard of my hotel bed and I slowly thrust my 8 inch vibrating dildo all the way in and out of me, while I slowly stroke my rock hard and leaking cock. The sensation makes me start to moan immediately. Feeling those dildo sliding in and out, as I continue to watch this hot, muscular bear fuck a hot your CD in missionary position drives me into a frenzy. I begin to pick up the pace as I grow more and more horny. I then lower myself and turn around and lay back and reposition my laptop. While I lay back, I raise my nyloned legs above the headboard. I’m at the point where I know I’m going to cum soon. The sensation of my dildo becomes more and more overwhelming. I turn up the vibration all the way and begin to fuck my self hard and fast. I don’t touch my cock as it sticks straight out of my crotchless body stocking and leaks precum. I’m moaning while I watch this hot CD dangle her legs over this studs shoulders and moan. After he came on the video, I couldn’t hold back any longer. The sensation grows and I begin to squirm and shake and have a massive full body orgasm. Cum shoots out of my cock and onto my body stocking and nighty, as I moan and shake on my bed. This was one of the most intense and longest orgams I’ve had in a long time. A nice and numb feeling comes over me post cum and I just lay back in bed with legs on the headboard for a good ten minutes after my explosive orgasm. I eventually compose myself and get up from my bed. After cleaning up, I slip on a black hoodie and jeans over my nighty and body stocking, and decide to head down stairs to hotel bar for a drink or two.
My mood was very laid back, as I sat at the hotel bar and ordered a drink. It was a Monday night in January and around 6pm. The bar was dead and was due to close early at 8pm. There was only woman working the bar and the booths in the bars area. . She a cute brunette in her early 20s, petite and fit. She was in a black collared shirt, black skirt, and black tights, while in white sneakers. I couldn’t keep my eyes off her. She was young and gorgeous and was constantly looking at her legs whenever she got out from behind the bar. I order another drink and get horny once again. The bartender/server and I chit chat when she has down time. Nothing special since our chats were short, as she was the only one working. At the bar by myself, I curiously look at who else is there. I see a couple in their 40s. The husband was attractive and bulky. He was bald and had a salt and pepper goatee. Sort of similar to the man in the porn video I had just watched. He never looked over thankfully as the rest of the time at the bar was spent either checking out him or the bartender. My cock begins to grow under my jeans and the feeling of nylon against my body feels much better as I stare at the bartenders nyloned legs, as she walks from behind the bar to clean up my stud’s table. At around 7:30, the bartender is all who is left. She tells me it’s last call. I order a drink and bring it up to my room with me. She says I could order two since I’m staying at the hotel, so I grab two vodka tonics, and sign my bill. I say goodbye to the bartender and get one last glance at her before I take my two drinks and head to my room. I ride up the elevator to the 18th floor and enter to my room.
As shut the door behind me and I place my two drinks down and take off my hoodie and pants. I turn on my laptop again and go back to my favorites folder, and find a favorite of mine. It’s a hotel orgy of all bears. Eight dream men going at it. I lay in my nighty and body stocking on my side, as I watch this video and sip my drink. Slowly rubbing myself, as I watch men sucking, rimming, and fucking one another. This is an hour plus video, so I can take my time. After I finish my drink, I hit pause and get off my bed and head to my new bag of goodies I purchased earlier in the afternoon. I pull out a matching cotton white bra, panties and white garter. I slide off my cum soaked body stocking and nighty and put on my bra and panties and pull up my white lace garter belt. I then pull out a pair of white opaque stockings and slide them on one by one and attach both to the garter. I finally grab the grey mini skirt and slide it up. In my new outfit, I get back in bed and start the video. I lean over and grab the dildo and lube again, that I had left on the bed. I apply lube to my hole and toy once again and turn on the dildo to medium vibrate and slide it in me all the way. I keep my dildo deep in me and then slide on my white cotton panties, to keep the dildo in place. The video continues and I grow rock hard again. Laying in a new outfit and feeling the sensation of the dildo vibrating inside of me. I quickly get up and grab my second drink and get back in bed. Watching this video and feeling more buzzed, my mind starts to wander once more.
My horniness starts to get the best of me and I open up a new tab on my browser and head to a Craigslist like personals site, that I have used for time to time. I had a good amount of experience with men when I was younger and single but not as much since I met my now wife, outside of a few one offs when I traveled other times or the wife was away and could have company. I go to the “guys for guys” section and stroll through the ads. I then see an ad that caught my eye.
“Horny married pilot. 55yo mwm 6’3 240 hairy 8cut short grey hair. I’m a top and looking my for a hot fun bottom. No one line responses and pic on first email. Fem, CD a plus. Let’s have some fun.”
I was intrigued since he has the exact type of body I’m most attracted to and he’s also married. More importantly, I was dressed and I knew it was something he’d be into. I put down my drink and took a sexy pic of myself on my laptop. I’m laying on my side smiling, with my rock hard cock noticeable under my panties. I pause for a second and compose my reply.
“Hi. I’m Steve, mwm as well. I’m 36yo 5’9 6cut handsome, dark hair, brown eyes. I’m alone in a hotel in Cambridge if you’re interested in chatting more. Am available all night. Hope to hear from you :) “
I hit send and then head back to my drink and video. His ad was posted a half hour before I replied so hoping he is real and didn’t find anyone. I continue to lay with dildo vibrating deep inside of me, under my panties, as I rub my pantied cock and sip my second drink. I keep going from the video, to my email inbox and spam folder to check for a reply. Nothing so far. I’m now 40 minutes into the video and 30 since I replied, and still nothing. As I watch the video, I notice I have a site message. I go to check and see it a friend I had chatted with many times on here and says “Hi baby”. I reply back and we get into our usual chitchat. He is married and in his early 40s and loves guys who dress up. He also loves roleplay chat and we often go to meet on Skype and occasional cam when we can. I chat with him while I watch the video, and monitor my inbox. About 30 minutes into our chat, he tells me his wife fell asleep and he is heading to his basement office. We agree to meet over on Skype and continue our chat. I send him the pic I had sent to the pilot earlier. He loved it and we started into a hot teacher/student role play. The chat is hot and intense. About another 30 minutes in on Skype, our roleplay winds down to the end and he asks me if we can cam. I say “of course baby” and I lean back in bed and position my laptop in front of me. Before my friend calls, I check my inbox once again and still nothing from the pilot. At this point, I assume he is a fake or he found someone. When I see the income call icon appear on my screen, I move on and focus on my friend. He is laying back on his chair completely naked and smiling at me and says “oh my god babe. I love your outfit”. I smile and thank him as he strokes his hard cock. I slowly slide down my white cotton panties and lay with my stockinged legs spread with my dildo deep in me. I start to fuck myself with my dildo and stroke my hard cock. As we stroke harder, he goes “cum in your mouth like you did last time.” I then flip my legs over my body as my face is inches away from my cock. I had did this the last time we cammed together so was happy to oblige. My friend watched me stroke and fuck myself hard and upside down while he strokes faster. I then start to moan loud and shake and shoot another huge load into my open mouth, while my bud closes his eyes and starts to cum on his hairy chest. I get back in normal position and we both chat and say how hot that was before signing off. It was another amazing orgasm. Out of curiosity, I check my inbox again after we log out of Skype and still nothing. I get out of bed and brush my teeth and wash my face. It’s now almost 10:30pm and no reply, so I plan to finish what’s left of my second drink and head to bed. I’m still in my outfit, as I plan to wear to bed minus the skirt. I pickup my cell phone and answer a couple of texts and then I check my inbox one last time. This time, I see a reply. I get nervous and excited right away. I had just cum but was intrigued and open the email. He says. “So hot Steve. Im Clayton, nice to meet you. Are you still looking? Let me know. I can host here at my place or travel. Here is a pic of me.” I looked at his pic and my mood changed quickly. He was tall, muscular, hairy with grey hair all over his body. He also had really nice hair and handsome. I couldn’t keep my eyes off the picture. I downed the rest of my drink and hit reply. I told him how much I liked his picture and can host him. I tell him I’m in Cambridge. He replied quickly and says his place is only 10 minutes from there. I tell him the hotel and my room # on the 18th floor. He replies back. “Yes!!!!! I will be there soon Steve.” I’m nervous and excited. I stand up and fix myself in the mirror. I pace nervously in the room as I wait. I eventually get back in bed and begin to rub myself as I wait. About 20 minutes after the pilot’s reply, the hotel phone rings.
I nervously pick up the phone. I hear a woman’s voice tell me that she is at front desk and there is a Clayton there to see me. I tell her I’ve been waiting for him and to send him up. She apologizes and says they have to check room keys after 10pm. I say no problem and I hang up. I get up from bed and walk to the door. The elevator is diagonal from my room. As I hear from my room the elevator floor stop at my floor, I open up the my room door. I see Clayton come out of elevator. Once I know it’s him, I whisper “hey” As looks for what direction to go. He then looks over and sees me in my outfit at my door. Clayton smiles and comes into my room and I close the door behind me. Clayton says “what a sexy surprise. You’re so hot Steve!” I smile as Clayton comes over and hugs me and then leans down to kiss me. We make out standing in my room, his strong hands all over my body. We share a long sensual kiss while we stand and rub on another. I then begin to kneel before Clayton and undo his belt and unzip his black pants. I pull down his pants and help him out of his shoes, while Clayton takes off his coat and unbuttons his light blue dress shirt. Clayton is now in black socks and his white briefs. I look up at him and tease his rock hard cock thru his briefs. Clayton let’s our a moan and closes his eyes. I lower his briefs to the floor and look up at him and smiles as me smiles back at me. I then open my mouth and massage his beautiful 8 inch cut cock with my lips. My cock begins to get hard a third time as I kneel before Clayton and work my lips back and forth while I look up at him, his eyes closed and moaning. He begins to rub my head and look down at me as I maintain eye contact and suck his big hard cock. After a good ten minutes enjoying Clayton’s big cock, he pulls me up and tells me to get in bed and bend over. I stand up and go the bed. I bury my head in a pillow near the headboard. Clayton reaches down and pulls out a condom from his pants pocket. He asks me if I have lube and point to the floor. He sees my dildo “wow baby, you’re in slut mode tonight”. He grabs the lube and gets in bed. My pantied pass in the air, as I feel Clayton’s presence behind me. I feel the stumble of his face as he plants his tongue into my wet hole. My cock is rock hard and pointing toward the bed. Clayton slides his tongue in me and flicks it back and forth and in and out, while he strokes my cock. I’m loving this and am making loud muffled moans while he strokes and tongue fucks me. I’m back in a frenzy for a third time since I landed 10 hours ago. My cock starts to swell in his hand and the feeling of tongue inside of me for so long was too much to take. I begin to shake and moan and shoot my third load of the night onto my bed. Clayton moans “oh yeah baby! Fucking hot!” as I shoot my load all over my bed beneath me. Clayton then pulls his tongue out of me and says “stay like that”. I hear the noise of Clayton ripping open the condom wrapper and putting it on his hard cock. He applies lube to his cock and slides it in. I pick my head up and turn to Clayton and tell him how hot he is and how good he feels in me. He starts to pound me from behind and he pulls my head back as I look back at him and kisses me, while his 8 inch cock effortlessly slid in and out of my eager hole. Clayton was the perfect man. Strong, attractive, hairy and a big cock. I’m in heaven. The room is filled with the sounds of our moans and the headboard slamming against the wall. After a little while, Clayton points to the table against the window in the corner of my room and says “go lay on that table baby”. I stand up and go over and remove the lamp and my drink glasses from the table. I lean back and bend my legs behind me as Clayton approaches the table. While standing, Clayton slides his cock into me, while I look up at him and moan. My nyloned feet pressed against the window behind me. Clayton aggressively fucks me on my table. He leans down as he gets closer and we kiss. I wrap my legs tightly around him as Clayton kisses me deeply and pounds me while I lay on my table and he stands. He then grabs by ankles and spreads me as wide as possible and fucks me fast. Both of us yelling as he tells me he’s going to cum. Clayton then keeps his cock buried deep and kisses me while he cums, as I wrap my legs around him. He then gets off of me and pulls out. He rolls off his cum filled condom and throws it into my trash, as I get up and get us towels from my bathroom. Clayton began to tell me how he has a lot of “trysts” like this in Boston when he has to stay here one week a month. He is from Texas but has to stay in Boston with his crew. Clayton asks me when I’m leaving and told him it was my first night in town and here for anther 8 days. His eyes lit up. Clayton then says. “I have to leave now because I need to meet my crew at 4am at our hotel. I’ll be in London for next two days but I’ll be back in Boston Thursday to Saturday night before I head back To Texas. I’d love to meet again.” I smile and tell him I’ll love that. We hug and make out before Clayton finishes getting dressed, and calls an Uber. Clayton says “I’ll look for you on email while I’m in London and we can chat more. I’d really love to see you again in another sexy outfit. Your body looks amazing dressed up like this.” Clayton then says goodbye and leaves. I lean back and smile. While still in my outfit, I turn off the lights and fall asleep.
I wake up the next morning and find an email from Clayton in my inbox. It says “Hi Steve. Wanted to thank you again for having me over. I want to see more of you. I wish your were one of my flight attendants. Lol. Let’s chat tonight if your free. I’ll be alone in my hotel thinking of you.” I reply, “I can’t wait to see you again. I already know what to wear for you next :). Will chat with you tonight. Xoxo Steve”. I got hard as I read Clayton’s email and began to jerk off once again in bed. I flipped myself over again and gave my self a mouthful of cum. My forth intense orgasm since I arrived. I laid down for a while before I got up to shower, grab lunch, and get ready for my meeting at 3pm. My mind was racing, knowing I’ll se Clayton again. To be continued….
2 ปี ที่ผ่านมาแล้ว
