Story from another sissy slut
I had only two experiences with a black man in my many years of cross-dressing. The guy I met in Pennsylvania was great....but got me into the mood to really be dominated and sissified by a black man before I retired and didnāt get the opportunities to arrange meetings like I did when I was working nine states! Most of my early cross-dressing years with my first wife I dressed up sexier and fem and role-played more with my wife than I dressed for others. After our divorce, I went for 3 or more years until I picked up where I left off and due to my new wifeās puritan ways, I went back to cross-dressing by myself in my hotel rooms and I enjoyed numerous evenings in my room with the second floor window open wearing silky sexy lingerie/hose and making love to my butt plug and 8" dildo. I did engage in about a half dozen "hotel meetings" during the last 30 years but mostly I took care of myself and felt safe and comfortable with my need to pass or prance around the mall while wearing lingerie. (I did get all silky and sexy in my hotel room, insert a butt plug with a maxi pad and panty girdle, hose and camisole under my jeans and tennis shoes and visit the adult book stores in the area. Iād come back to my room after watching tv/cd movies and have a ball getting myself off while riding my nice fat 8" black life like dildo!)
I decided Iād pursue the possibility of meeting with a black man in a hotel room making sure he agreed to be gentle and understanding while making my fantasy come true. I wanted to be his white sissy boy....wearing femmy lingerie/hose with full makeup, wig, nail polish and perfume. I wanted him to tell me what to do and take me completely like the sissy boy I was! My search on the net began and within a couple weeks I was corresponding with a black divorce Kroger store manager in Detroit, MI. He was 58...almost the same age as I was when we had this encounter. He liked cd's/tv's and he was very excited about helping me experience my fantasy. (Especially when we found out I was an x Detroiter and A&P store manager in my younger days.) He liked being in control and as far as giving me what I was looking for, he had a few other surprises up his sleeve and we made me promise Id do what he told me too all night long. My hands trembled on the keyboard as I asked him what he wanted me to do............knowing I was getting in deep as this time and there may be no turning back. My curioursity got the best of me and I really wanted to please him while he promised to full fill my desires.
I was going to be in Detroit in 2 weeks. We picked a nice hotel by the airport and he told me I should get there early enough to leave plenty of time to prepare myself exactly like he wanted. It was the longest two weeks ever. I had to tell him what I had for lingerie/hose, etc. and he gave me a list of what he wanted me to wear that I had already and a few things I had to buy. I think he knew Iād be excited about searching out the items on the list and buying the rather intimate items I didnāt have. By the time the day came for me to drive to Detroit for our meeting I was a nervous wreck. I didnāt plan any business meetings the day of my drive or before noon the next day. This was going to probably be my last chance to do something like this....I felt good about my internet connection and I was so anxious to prepare myself for my dominate lover and "give myself up" to him wholly! (that has always been my favorite part of meeting someone; getting all silky and sexy and femmy for my lover)
It was a long ride to Detroit...my mind racing about meeting this black man and what I was going to do to get ready for him and hoping that he'd like my outfit and me!!! I relived my meeting with the black guy in Pennsylvania and wished I had asked him to come to my room while I was all fem and silky and let him make made passionate love to me. My cock was hard almost the whole way to Detroit and my hands were shaking as I signed in at the hotel....second floor, king size bed with microwave and fridge. And yes, this was the hotel that had full size mirrors for closet doors and the entire kind size bed was visible in them!!! I threw my bags on the bed, stripped down naked, lay out my toiletries in the bath room and unpacked my 4pak of strawberry douche and some ky.
I laid a bath towel on the bed and laid back on my back-lubed up one of the nozzles of the douche bottles and slowly pushed inside me all the way and emptied out the contents deep in my bowels. When empty I took it out and inserted another one...filled me with sweet smelling douche and I laid there for a short time while the douche did its job. I got up, hurried to the bathroom with my ass cheeks clenched together tightly and expelled the fluid from my ass. OH my...was that nice. I always do this at least twice to make sure Iām good and cleaned out...so back I went to the bed only this time I got on my hands and knees and put the remaining two bottles of douche in my ass. I stayed on my elbows and knees for a while...feeling the sweet fluids flowing in a different direction in my tummy until I felt the urgent need to empty out. After that I took a nice hot shower, shaved and powdered all over. I trimmed my groin area and shaved my ass as well. I then went back to the bed, laid on the towel and took out my 6" medium size butt plug, added some KY to it and placed the base of the plug on the towel and the tip against my tight ass. I slowly began to move my hips and slide the top 1/2 of the plug inside me....OHHHHHHHHH did that feel good. I rested...then moved up and down and the plug until I could feel the fattest part of it spreading my ass open wide. I took a breath, tried my best to relax my spinster muscles and applied more downward pressure until it POPPED in! WOW.....It felt wonderful and I was so turned on but not nearly ready for playtime. I wiped off the KY on my ass that was around the base of my butt plug, put on an old panty girdle with a maxi pad. This was going to help me open up a bit in preparation for bigger things to come!
Dutch was the manās name that wanted to bring my fantasy to fulfillment. He was very specific and what I was to wear and do to get ready for him. Shaving my ass was one thing...next I was to put polish on my toes and fingers, BRIGHT RED. So I sat down on the toilet and propped my feet up on the side of the bath tub and put polish on my toe nails....then my finger nails, all the while my butt plug was filling up my ass and feeling really good. I then walked into the main bedroom and stood by the window while my polish was drying. I was trying to be patient and let my polish dry enough before I put on my "outfit" that was all spread out on the kind size bed. Can I go thru with this? Was Dutch going to be safe and not hurt me? I was going to be so vulnerable when he walked in my door....no turning back...hopefully no regrets. As my mind buzzed I squeezed my ass cheeks together to feel my plug move in and out a bit. Still safely tucked deep inside me and making me ache for release. Not yet! Not now! I needed to get dressed so I would not give in to my lust and cum too soon!
I shook my head and released my mind from what was to come. At least what I imagined what was to come? I checked my nails....ok dry. I took off my panty girdle and went into the bathroom to take out my plug and wash off really good. The KY still buried deep inside was going to help lube up my partners hard cock on entry the first time. He told me he was circumcised and approx 8" and thick around the middle. He didnāt think he'd need any pills to keep him up...that was my job!!! OH MY....My mouth was aching before I even got dressed. I then moved to the bed and started putting on my outfit most of what was bought new just for the occasion. My last hurrah, why not go first class. Dutch wanted all aspects of my manliness hidden. My leg hair covered good and no mustache. I did remove my mustache for the last time since. He wanted me in white....and sissy pink. Glossy legs and frilly panties (Like tap pants) A filmy lace and nylon short nighty, wig and makeup. So, I found a dance shop in Dayton up on the north side. I got glossy white shinny lots of lycra pantyhose and frilly dance panties. I had one of my wifeās white bras that I stuffed with water balloons (Dutch wanted "decent size" boobs) and I found a pink and white nylon baby doll outfit with lace 3/4 sleeves and bottom hem line lace. Just right for covering up any hair and muscles. I pulled on the hose first pausing with them at my knees and I cut a hole in the sewn in cotton crotch in just the right location of my ass. I then pulled them up and the control top felt good holding in my tummy and making my ass nice and rounded. I checked to make sure the hole in the crotch was positioned just right and that the back seam was straight. The tight hose with the small slit made my ass cheeks poke thru and it looked like pussy lips...and felt really sexy! I had pushed my balls up inside my groin and pulled my half hard cock back between my silky legs. A shortened up maxi pad covered me up and kept me nice and hidden. I looked at my shinny white legs with my bright red polished toes nails showing and I was shaking with excitement. Next was the frilly panties that I also cut a small slit in the back to allow easy access while keeping on my complete outfit. Then my bra.....oh my bra....my hands were still shaking while I hooked the front enclosure. (yes, it was a front loader bra...my favorite). I then went into the bathroom with my two white heavy party balloons and ran the water until almost tepid. I filled them up to a nice c size and double tied the top so they would look like nipples in my bra. I placed them in my bra and looked at myself in the bathroom mirror....WOW, I was white and sexy and the transformation was working well. By now I was getting nervous...and shaky...so I opened the bottle of Merlot that I brought and sat down on the big overstuffed couch and sipped on my wine for about 15 minutes or so. I needed to settle down before putting on makeup and wig. Time was getting close...I had allowed myself plenty of time but I didnāt realize how fast things were moving so I sprung up from the couch and heading for the bathroom again to put on my face! Thankfully I did a lot of make up during my earlier years as the wife helped me and used me for her model in some of her Holiday Magic parties to practice on.
Dutch wanted heavier makeup than just the everyday look but not slutty. OK, what does that mean? I started with some eye liner, then mascara, then white shadow and dark eye brows to match my eye liner. I put on some red blush and red lipstick. Glossy and oh so yummy. Then I put on some light powder and perfume and a 2 strand fake pearl necklace that I found at a garage sale. I pulled out my red shoulder length wavy wig that I also found at a garage sale....put it on and combed it out...WOW. I finally stopped long enough to admire my fem self in the mirror. I was lookin pretty good for a 6'1" man weighing in at 245 pounds. I practically ran into the bedroom and put on my shorty baby doll and stood in front of the full length mirror in awe. I looked good enough to fuck and run away with! It was sooooooooo long since I did this. Fully dressed in fem...makeup, wig, polish, perfume...and an ass pussy that wanted/needed to be filled with a black manās cock! What made it all come to this? Now that I was all ready could I really open the door and let it happen? Completely surrender myself to a stranger, a black man, an unknown? I said a silent prayer while pouring another glass of wine and got things ready for my company. Hand towels, lube and condoms on the bed side stand; lights turned down low; soft music playing and the curtains opened wide. I turned on the ac so I didnāt roast especially when the action got heated up. I stood in front of the window sipping my wine watching the sun go down and wondering if anyone could see this white silky femmy sissified 58 year old male waiting for his date to show up.
Then the phone call.........it was him. He didnāt say hi nor was I ready just what room?!? I told him 215 and he hung up. My heart was pounding out of my chest and my cock was so shriveled I thought I lost it forever. Of course it was all tucked away out of sight and mind but I just knew it was as scared silly as I was...Then the knock on the door. I put my wine glass down and slowly walked towards the door unlatching the chain and opening up the heavy door. He stood there filling the entire door way with his body. Big 6'3" frame and about 250 pounds....a bit of a beer belly like mine but large arms and short crew cut hair. He was not black black but a nice tan brown and fairly good looking. I stood back from the door and he just looked at me up and down...up and down...then again up and down stopping at my eyes and looking at me intently. "I think you'll do just fine you sissy white boy fag!" He walked in the door closing it behind him as I stepped backwards several steps basically spell bound by this hunk who just called me a sissy white boy fag! It was then I realized that I did what he wanted, looked like he wanted me to look like and I felt a warm rush comes over my entire body. Yes, it was the wine and the moment! I was so ready to yield to this man as my mind slowly went to a different place. I was prepared to give myself to him and be his sissy white boy fag!
He told me to sit on the edge of the bed as he took off his coat and sweatshirt, shoes and socks. Then he moved over in front of me and told me to unbuckle his belt and unzip his zipper.....slowly! My trembling hands grabbed his belt buckle and I fumbled trying to undo it...then unzip his zipper. I could feel the bulge in his underwear and knew he was getting hard already. As I unzipped his pants he opened up his jeans and let them fall to the floor and all he had on was jockey shorts. Then he started to whisper to me..."boy, this black man is gonna fuck your sissy white ass pussy like you've never been fucked before. By the end of the night you're gonna know what itās like to be a sissy slut to a black man and youāre gonna love it. Now pull my undies down and see what a nice surprise I got for you!" Oh man was I getting hot now....and my hands were really shaking as I pulled down his shorts to reveal a beautiful black cut cock Shaved and smelling oh so good! It was about half hard and it was my job to get him as hard as possible. I put my hands around his cock and cupped his big sack of balls. I got my face as close as I could to look at him and admire the cock that was going to soon be inside my waiting ass and breed me black! He asked me if I liked what I see and of course I shook my head yes.....He then yelled out "I can hear you you pussy whipped slut! Tell me that you love my big black cock and you want to suck it!" Oh my, did I want to suck it. I told him his cock was beautiful and I wanted it so bad and with that I took him in my mouth as much as I was practically gagging on the first gulp. He was big around and seemed like more than 8" by the time he stiffened up all the way. He grabbed my head with his big hands and started to pump my mouth with his cock. It was all I could do to breath and try to concentrate on sucking him. He was so hard and I could feel him tighten up....he was going to cum and I didnāt put a condom on him yet. I tried to back away to tell him I needed to put a condom on him (I had told him that was a condition for oral and anal sex) but he kept on pumping my face.....I was about to gag when he pulled his cock out of my mouth, grabbed his cock and jacked off on my face. I couldnāt believe it. All this time to prepare for him and after 15 minutes in my room he came all over my face!!! He moaned like a wild moose on the tundra and sat back on the desk behind him and steadied himself. His cock was glistening with cum and still fairly erect. He looked at me and reminded me that he had a few surprises for me...that was one of them. Then he told me to go clean up and get back in here and meet him in bed. My legs were wobbly as I went into the bathroom to wash my face and fix my makeup.
When I came back out to the bedroom, Dutch was laying on his back in the middle of my king size bed. He was naked and his mighty thighs were opened up wide and he was massaging his big cock and when he seen me he pointed his cock at me and said āI hope you didnāt think that I was done with you sissy. I have lots more cum for you to enjoy now get over here between my legs and take over." Oh my, he didnāt have to ask twice as I quickly got on my knees between his legs and grabbed his cock and moved down to lick it like a lolly pop! It was beautiful up close...black and shinny and his cap was so pronounced and oh so hard!
I licked him and began to slowly put him in my mouth and suck each precious inch as he arched up his back to shove in his stiffening cock further down my throat. He started telling me how good I was...what a sweet slutty sissy cock sucker I was. He told me how bad he wanted to stuff his big black cock up my sissy ass pussy and fill me with black cum. Oh man, I was getting dizzy hearing him talk, my ass up high in the air and my head down between his thighs! The wine was kicking in as well and I felt like I was in a different time and place. I was totally immersed in the act of satisfying this black man as his white sissy fag. After what seemed like an hour (it was only 20 minutes or so) he told me he wanted me to sit on his big black cock and bury it in my sissy ass! I reached over to the bed stand and grabbed lubed condom and put it on him. I knew I was still wet inside my ass from the lubed plug I had in earlier so I decided to forego the KY and try him without too much lubrication. I got up and was going to sit on him facing him....he stopped me. Turn around sissy and sit on my facing my feet; I want to see my black cock fucking your white sissy ass pussy! I turned around the opposite direction and sat back down slowly...he pulled my panties open and placed his cock head at the entrance to my ass thru the small opening on my pantyhose. He grabbed my hips and started pulling me down on his cock....slowly. The head was so big....I was second guessing myself on the lube situation..But as he pushed against me I loosened up enough to feel the head of his cock pop inside me. I let out a small whine....he took a big breath. "Baby my black cock in your sissy white ass is absolutely beautiful!" Then he stared to slowly work his cock deeper inside me....pulling my hips down and shoving his cock up inside me until I could feel his balls against my ass cheeks. Once all the way inside me, he just held me there and I could feel his cock throbbing deep inside me. I had this black mans big cock all the way in me...and It felt WONDERFUL!!!
My legs needed to move...so I began to rock a little on his cock...then he released his grip on my hips and let me start to move up and down on his cock. Oh my did It feel soooooooooooo good. He held still and let me do all the work (it really wasnāt work!) and I picked up the pace and really started to ride him. My cock was so tight inside my maxi pad and hose...I was breathing like crazy and getting dizzy with the pleasure treatment my ass was getting. After all my prep and anxiety, it was paying off in spades. This was fun!!! I got lost in the moment until my lover grabbed my hips and stopped me from moving. He told me NOT YET SISSY.....He pulled out of me and told me to lie on my stomach next to him. It was a welcomed move as my legs were getting weary from the position I was in. I laid down on my stomach as he rolled over and parted my silky legs. He then moved between my legs and put his cock at the entrance to my ass pussy and told me that he was going to fuck me silly and with one long quick move he shoved his cock in my ass all the way until I felt his balls slapping against my ass cheeks. He lowered himself down on top of me (I love this position) and started pumping me with his hot hard black cock. He started too grown and breathes heavy....then without warning he put his legs outside of mine and moved my legs tightly together. He had his cock all the way inside me when he did this. He told me how hot and tight I was for a white sissy fag and he was going to cum deep inside my sissy ass pussy. He moved his cock in and out very slowly as I rubbing my silky legs together and flexed my ass muscles around him. I was about ready to cum myself as he massaged my prostrate with his big cock. It was tight...and he loved it. He remembered that I told him this was my favorite position and he was liken it too! He was really verbalizing in my ear how tight and hot I was...how wet and ready I was for him...how much he was enjoying fucking a white sissy fag like me and how he was going to spoil me for black cock forever! Then he started to move a little faster and I could feel him get bigger and ready to cum. Just before he did, he told me he was going to breed me black and fill my tight sissy ass pussy with his black seed making me his forever! He then took a mighty shove inside me and held his cock in deep as he shuddered and shook and came hard and long. He moaned and groaned and his legs pressed against mine tightly as his arms held me down and his hips slammed me hard.
I was getting close to cumming, and my head was spinning. My ass felt so good and I was grinning because I really got this guy hot and horny for me. It was one of the best fucks I ever had and I had to be 58 years old to experience it....We both just laid there for a while as he tried to get his breathing back to normal as well as mine. He loved the way his cock felt inside me with my legs tight together....I wiggled my ass a bit and flexed my ass muscles and he chuckled a little at my actions. He slowly moved back as his semi limp cock fell out of my ass. He laid down next to me to rest and put his big black hand on my ass as he told me how great it was and how much he pleased me. I told him I was glad because he really helped me realize my fantasy as well.
He told me he had one last surprise for me and was I ready?! OK, as my curiosity was going double speed. He told me to go into the bathroom, get the shower going and take off everything except my hose. UMMMMMM what did he have in mind? Oh well, I got up and did what he asked. I took off my lingerie, bra and frilly panties. He came in naked and told me to join him in the shower. We got in and he told me to wash his cock good so I took the soap and wash rag and started washing his cock as he pushed on my shoulders to put me on my knees in the tub. I rinsed him off and he took my head and pulled it towards his now very clean and semi hard cock. He told me to Worship his black beauty and thank it for being so good to me tonight. I kissed his cock and licked it up and down and around his cock head. I licked his clean hairless balls and let his cock rub against my face. He asked me if I enjoyed his black cock tonight. Did I like what he did to his white sissy fag? OH YES<<< OH YES.....I whispered in a heavy voice as I licked his cock and played with his balls. He grabbed my head once again and put his cock in my mouth as far as he could before I gagged. Oh my, what a surprise that was. He pumped very slowly in my mouth and then pulled out and told me to close my mouth and eyes. I did and he peed all over my face and chest!!!! It seemed like eternity before he finally emptied his bladder all over me. I was so shocked I was speechless. I just sat there in the tub on my knees with water and his pee cascading all over the front of me. He got out of the shower, grabbed a towel and told me to stay there until he told me to move. He left the bathroom with me still in the tub and the water flowing over me. I put my hands on my face to wash off the remments of his urine and let the water cleanse me.....Then I heard the door slam! I turned off the water and grabbed a towel and looked out the bathroom door........he was gone.
I was exhausted as I took off my hose and released my poor cock. I dried off and as I walked into the bedroom to pour another glass of wine my cell phone rang. It was him. He told me that he leaving me in the tub without saying goodbye was his last surprise. He told me I was a great fuck and he really enjoyed doing all the things he did to me for me and him. He'll always remember his white sissy fag! Then hung up.
Ill never forget that night either...My sissy fantasy realized I put on lace top thi hi's, silky bikini panties and a silky nighty and climbed into bed tired yet so fulfilled and surprised at what I did to chalk up another wonderful sexual experience on my bucket list! As I drifted off to sleep, I could still feel his big black cock buried inside me....my ass was still twitching and yearning for more
I decided Iād pursue the possibility of meeting with a black man in a hotel room making sure he agreed to be gentle and understanding while making my fantasy come true. I wanted to be his white sissy boy....wearing femmy lingerie/hose with full makeup, wig, nail polish and perfume. I wanted him to tell me what to do and take me completely like the sissy boy I was! My search on the net began and within a couple weeks I was corresponding with a black divorce Kroger store manager in Detroit, MI. He was 58...almost the same age as I was when we had this encounter. He liked cd's/tv's and he was very excited about helping me experience my fantasy. (Especially when we found out I was an x Detroiter and A&P store manager in my younger days.) He liked being in control and as far as giving me what I was looking for, he had a few other surprises up his sleeve and we made me promise Id do what he told me too all night long. My hands trembled on the keyboard as I asked him what he wanted me to do............knowing I was getting in deep as this time and there may be no turning back. My curioursity got the best of me and I really wanted to please him while he promised to full fill my desires.
I was going to be in Detroit in 2 weeks. We picked a nice hotel by the airport and he told me I should get there early enough to leave plenty of time to prepare myself exactly like he wanted. It was the longest two weeks ever. I had to tell him what I had for lingerie/hose, etc. and he gave me a list of what he wanted me to wear that I had already and a few things I had to buy. I think he knew Iād be excited about searching out the items on the list and buying the rather intimate items I didnāt have. By the time the day came for me to drive to Detroit for our meeting I was a nervous wreck. I didnāt plan any business meetings the day of my drive or before noon the next day. This was going to probably be my last chance to do something like this....I felt good about my internet connection and I was so anxious to prepare myself for my dominate lover and "give myself up" to him wholly! (that has always been my favorite part of meeting someone; getting all silky and sexy and femmy for my lover)
It was a long ride to Detroit...my mind racing about meeting this black man and what I was going to do to get ready for him and hoping that he'd like my outfit and me!!! I relived my meeting with the black guy in Pennsylvania and wished I had asked him to come to my room while I was all fem and silky and let him make made passionate love to me. My cock was hard almost the whole way to Detroit and my hands were shaking as I signed in at the hotel....second floor, king size bed with microwave and fridge. And yes, this was the hotel that had full size mirrors for closet doors and the entire kind size bed was visible in them!!! I threw my bags on the bed, stripped down naked, lay out my toiletries in the bath room and unpacked my 4pak of strawberry douche and some ky.
I laid a bath towel on the bed and laid back on my back-lubed up one of the nozzles of the douche bottles and slowly pushed inside me all the way and emptied out the contents deep in my bowels. When empty I took it out and inserted another one...filled me with sweet smelling douche and I laid there for a short time while the douche did its job. I got up, hurried to the bathroom with my ass cheeks clenched together tightly and expelled the fluid from my ass. OH my...was that nice. I always do this at least twice to make sure Iām good and cleaned out...so back I went to the bed only this time I got on my hands and knees and put the remaining two bottles of douche in my ass. I stayed on my elbows and knees for a while...feeling the sweet fluids flowing in a different direction in my tummy until I felt the urgent need to empty out. After that I took a nice hot shower, shaved and powdered all over. I trimmed my groin area and shaved my ass as well. I then went back to the bed, laid on the towel and took out my 6" medium size butt plug, added some KY to it and placed the base of the plug on the towel and the tip against my tight ass. I slowly began to move my hips and slide the top 1/2 of the plug inside me....OHHHHHHHHH did that feel good. I rested...then moved up and down and the plug until I could feel the fattest part of it spreading my ass open wide. I took a breath, tried my best to relax my spinster muscles and applied more downward pressure until it POPPED in! WOW.....It felt wonderful and I was so turned on but not nearly ready for playtime. I wiped off the KY on my ass that was around the base of my butt plug, put on an old panty girdle with a maxi pad. This was going to help me open up a bit in preparation for bigger things to come!
Dutch was the manās name that wanted to bring my fantasy to fulfillment. He was very specific and what I was to wear and do to get ready for him. Shaving my ass was one thing...next I was to put polish on my toes and fingers, BRIGHT RED. So I sat down on the toilet and propped my feet up on the side of the bath tub and put polish on my toe nails....then my finger nails, all the while my butt plug was filling up my ass and feeling really good. I then walked into the main bedroom and stood by the window while my polish was drying. I was trying to be patient and let my polish dry enough before I put on my "outfit" that was all spread out on the kind size bed. Can I go thru with this? Was Dutch going to be safe and not hurt me? I was going to be so vulnerable when he walked in my door....no turning back...hopefully no regrets. As my mind buzzed I squeezed my ass cheeks together to feel my plug move in and out a bit. Still safely tucked deep inside me and making me ache for release. Not yet! Not now! I needed to get dressed so I would not give in to my lust and cum too soon!
I shook my head and released my mind from what was to come. At least what I imagined what was to come? I checked my nails....ok dry. I took off my panty girdle and went into the bathroom to take out my plug and wash off really good. The KY still buried deep inside was going to help lube up my partners hard cock on entry the first time. He told me he was circumcised and approx 8" and thick around the middle. He didnāt think he'd need any pills to keep him up...that was my job!!! OH MY....My mouth was aching before I even got dressed. I then moved to the bed and started putting on my outfit most of what was bought new just for the occasion. My last hurrah, why not go first class. Dutch wanted all aspects of my manliness hidden. My leg hair covered good and no mustache. I did remove my mustache for the last time since. He wanted me in white....and sissy pink. Glossy legs and frilly panties (Like tap pants) A filmy lace and nylon short nighty, wig and makeup. So, I found a dance shop in Dayton up on the north side. I got glossy white shinny lots of lycra pantyhose and frilly dance panties. I had one of my wifeās white bras that I stuffed with water balloons (Dutch wanted "decent size" boobs) and I found a pink and white nylon baby doll outfit with lace 3/4 sleeves and bottom hem line lace. Just right for covering up any hair and muscles. I pulled on the hose first pausing with them at my knees and I cut a hole in the sewn in cotton crotch in just the right location of my ass. I then pulled them up and the control top felt good holding in my tummy and making my ass nice and rounded. I checked to make sure the hole in the crotch was positioned just right and that the back seam was straight. The tight hose with the small slit made my ass cheeks poke thru and it looked like pussy lips...and felt really sexy! I had pushed my balls up inside my groin and pulled my half hard cock back between my silky legs. A shortened up maxi pad covered me up and kept me nice and hidden. I looked at my shinny white legs with my bright red polished toes nails showing and I was shaking with excitement. Next was the frilly panties that I also cut a small slit in the back to allow easy access while keeping on my complete outfit. Then my bra.....oh my bra....my hands were still shaking while I hooked the front enclosure. (yes, it was a front loader bra...my favorite). I then went into the bathroom with my two white heavy party balloons and ran the water until almost tepid. I filled them up to a nice c size and double tied the top so they would look like nipples in my bra. I placed them in my bra and looked at myself in the bathroom mirror....WOW, I was white and sexy and the transformation was working well. By now I was getting nervous...and shaky...so I opened the bottle of Merlot that I brought and sat down on the big overstuffed couch and sipped on my wine for about 15 minutes or so. I needed to settle down before putting on makeup and wig. Time was getting close...I had allowed myself plenty of time but I didnāt realize how fast things were moving so I sprung up from the couch and heading for the bathroom again to put on my face! Thankfully I did a lot of make up during my earlier years as the wife helped me and used me for her model in some of her Holiday Magic parties to practice on.
Dutch wanted heavier makeup than just the everyday look but not slutty. OK, what does that mean? I started with some eye liner, then mascara, then white shadow and dark eye brows to match my eye liner. I put on some red blush and red lipstick. Glossy and oh so yummy. Then I put on some light powder and perfume and a 2 strand fake pearl necklace that I found at a garage sale. I pulled out my red shoulder length wavy wig that I also found at a garage sale....put it on and combed it out...WOW. I finally stopped long enough to admire my fem self in the mirror. I was lookin pretty good for a 6'1" man weighing in at 245 pounds. I practically ran into the bedroom and put on my shorty baby doll and stood in front of the full length mirror in awe. I looked good enough to fuck and run away with! It was sooooooooo long since I did this. Fully dressed in fem...makeup, wig, polish, perfume...and an ass pussy that wanted/needed to be filled with a black manās cock! What made it all come to this? Now that I was all ready could I really open the door and let it happen? Completely surrender myself to a stranger, a black man, an unknown? I said a silent prayer while pouring another glass of wine and got things ready for my company. Hand towels, lube and condoms on the bed side stand; lights turned down low; soft music playing and the curtains opened wide. I turned on the ac so I didnāt roast especially when the action got heated up. I stood in front of the window sipping my wine watching the sun go down and wondering if anyone could see this white silky femmy sissified 58 year old male waiting for his date to show up.
Then the phone call.........it was him. He didnāt say hi nor was I ready just what room?!? I told him 215 and he hung up. My heart was pounding out of my chest and my cock was so shriveled I thought I lost it forever. Of course it was all tucked away out of sight and mind but I just knew it was as scared silly as I was...Then the knock on the door. I put my wine glass down and slowly walked towards the door unlatching the chain and opening up the heavy door. He stood there filling the entire door way with his body. Big 6'3" frame and about 250 pounds....a bit of a beer belly like mine but large arms and short crew cut hair. He was not black black but a nice tan brown and fairly good looking. I stood back from the door and he just looked at me up and down...up and down...then again up and down stopping at my eyes and looking at me intently. "I think you'll do just fine you sissy white boy fag!" He walked in the door closing it behind him as I stepped backwards several steps basically spell bound by this hunk who just called me a sissy white boy fag! It was then I realized that I did what he wanted, looked like he wanted me to look like and I felt a warm rush comes over my entire body. Yes, it was the wine and the moment! I was so ready to yield to this man as my mind slowly went to a different place. I was prepared to give myself to him and be his sissy white boy fag!
He told me to sit on the edge of the bed as he took off his coat and sweatshirt, shoes and socks. Then he moved over in front of me and told me to unbuckle his belt and unzip his zipper.....slowly! My trembling hands grabbed his belt buckle and I fumbled trying to undo it...then unzip his zipper. I could feel the bulge in his underwear and knew he was getting hard already. As I unzipped his pants he opened up his jeans and let them fall to the floor and all he had on was jockey shorts. Then he started to whisper to me..."boy, this black man is gonna fuck your sissy white ass pussy like you've never been fucked before. By the end of the night you're gonna know what itās like to be a sissy slut to a black man and youāre gonna love it. Now pull my undies down and see what a nice surprise I got for you!" Oh man was I getting hot now....and my hands were really shaking as I pulled down his shorts to reveal a beautiful black cut cock Shaved and smelling oh so good! It was about half hard and it was my job to get him as hard as possible. I put my hands around his cock and cupped his big sack of balls. I got my face as close as I could to look at him and admire the cock that was going to soon be inside my waiting ass and breed me black! He asked me if I liked what I see and of course I shook my head yes.....He then yelled out "I can hear you you pussy whipped slut! Tell me that you love my big black cock and you want to suck it!" Oh my, did I want to suck it. I told him his cock was beautiful and I wanted it so bad and with that I took him in my mouth as much as I was practically gagging on the first gulp. He was big around and seemed like more than 8" by the time he stiffened up all the way. He grabbed my head with his big hands and started to pump my mouth with his cock. It was all I could do to breath and try to concentrate on sucking him. He was so hard and I could feel him tighten up....he was going to cum and I didnāt put a condom on him yet. I tried to back away to tell him I needed to put a condom on him (I had told him that was a condition for oral and anal sex) but he kept on pumping my face.....I was about to gag when he pulled his cock out of my mouth, grabbed his cock and jacked off on my face. I couldnāt believe it. All this time to prepare for him and after 15 minutes in my room he came all over my face!!! He moaned like a wild moose on the tundra and sat back on the desk behind him and steadied himself. His cock was glistening with cum and still fairly erect. He looked at me and reminded me that he had a few surprises for me...that was one of them. Then he told me to go clean up and get back in here and meet him in bed. My legs were wobbly as I went into the bathroom to wash my face and fix my makeup.
When I came back out to the bedroom, Dutch was laying on his back in the middle of my king size bed. He was naked and his mighty thighs were opened up wide and he was massaging his big cock and when he seen me he pointed his cock at me and said āI hope you didnāt think that I was done with you sissy. I have lots more cum for you to enjoy now get over here between my legs and take over." Oh my, he didnāt have to ask twice as I quickly got on my knees between his legs and grabbed his cock and moved down to lick it like a lolly pop! It was beautiful up close...black and shinny and his cap was so pronounced and oh so hard!
I licked him and began to slowly put him in my mouth and suck each precious inch as he arched up his back to shove in his stiffening cock further down my throat. He started telling me how good I was...what a sweet slutty sissy cock sucker I was. He told me how bad he wanted to stuff his big black cock up my sissy ass pussy and fill me with black cum. Oh man, I was getting dizzy hearing him talk, my ass up high in the air and my head down between his thighs! The wine was kicking in as well and I felt like I was in a different time and place. I was totally immersed in the act of satisfying this black man as his white sissy fag. After what seemed like an hour (it was only 20 minutes or so) he told me he wanted me to sit on his big black cock and bury it in my sissy ass! I reached over to the bed stand and grabbed lubed condom and put it on him. I knew I was still wet inside my ass from the lubed plug I had in earlier so I decided to forego the KY and try him without too much lubrication. I got up and was going to sit on him facing him....he stopped me. Turn around sissy and sit on my facing my feet; I want to see my black cock fucking your white sissy ass pussy! I turned around the opposite direction and sat back down slowly...he pulled my panties open and placed his cock head at the entrance to my ass thru the small opening on my pantyhose. He grabbed my hips and started pulling me down on his cock....slowly. The head was so big....I was second guessing myself on the lube situation..But as he pushed against me I loosened up enough to feel the head of his cock pop inside me. I let out a small whine....he took a big breath. "Baby my black cock in your sissy white ass is absolutely beautiful!" Then he stared to slowly work his cock deeper inside me....pulling my hips down and shoving his cock up inside me until I could feel his balls against my ass cheeks. Once all the way inside me, he just held me there and I could feel his cock throbbing deep inside me. I had this black mans big cock all the way in me...and It felt WONDERFUL!!!
My legs needed to move...so I began to rock a little on his cock...then he released his grip on my hips and let me start to move up and down on his cock. Oh my did It feel soooooooooooo good. He held still and let me do all the work (it really wasnāt work!) and I picked up the pace and really started to ride him. My cock was so tight inside my maxi pad and hose...I was breathing like crazy and getting dizzy with the pleasure treatment my ass was getting. After all my prep and anxiety, it was paying off in spades. This was fun!!! I got lost in the moment until my lover grabbed my hips and stopped me from moving. He told me NOT YET SISSY.....He pulled out of me and told me to lie on my stomach next to him. It was a welcomed move as my legs were getting weary from the position I was in. I laid down on my stomach as he rolled over and parted my silky legs. He then moved between my legs and put his cock at the entrance to my ass pussy and told me that he was going to fuck me silly and with one long quick move he shoved his cock in my ass all the way until I felt his balls slapping against my ass cheeks. He lowered himself down on top of me (I love this position) and started pumping me with his hot hard black cock. He started too grown and breathes heavy....then without warning he put his legs outside of mine and moved my legs tightly together. He had his cock all the way inside me when he did this. He told me how hot and tight I was for a white sissy fag and he was going to cum deep inside my sissy ass pussy. He moved his cock in and out very slowly as I rubbing my silky legs together and flexed my ass muscles around him. I was about ready to cum myself as he massaged my prostrate with his big cock. It was tight...and he loved it. He remembered that I told him this was my favorite position and he was liken it too! He was really verbalizing in my ear how tight and hot I was...how wet and ready I was for him...how much he was enjoying fucking a white sissy fag like me and how he was going to spoil me for black cock forever! Then he started to move a little faster and I could feel him get bigger and ready to cum. Just before he did, he told me he was going to breed me black and fill my tight sissy ass pussy with his black seed making me his forever! He then took a mighty shove inside me and held his cock in deep as he shuddered and shook and came hard and long. He moaned and groaned and his legs pressed against mine tightly as his arms held me down and his hips slammed me hard.
I was getting close to cumming, and my head was spinning. My ass felt so good and I was grinning because I really got this guy hot and horny for me. It was one of the best fucks I ever had and I had to be 58 years old to experience it....We both just laid there for a while as he tried to get his breathing back to normal as well as mine. He loved the way his cock felt inside me with my legs tight together....I wiggled my ass a bit and flexed my ass muscles and he chuckled a little at my actions. He slowly moved back as his semi limp cock fell out of my ass. He laid down next to me to rest and put his big black hand on my ass as he told me how great it was and how much he pleased me. I told him I was glad because he really helped me realize my fantasy as well.
He told me he had one last surprise for me and was I ready?! OK, as my curiosity was going double speed. He told me to go into the bathroom, get the shower going and take off everything except my hose. UMMMMMM what did he have in mind? Oh well, I got up and did what he asked. I took off my lingerie, bra and frilly panties. He came in naked and told me to join him in the shower. We got in and he told me to wash his cock good so I took the soap and wash rag and started washing his cock as he pushed on my shoulders to put me on my knees in the tub. I rinsed him off and he took my head and pulled it towards his now very clean and semi hard cock. He told me to Worship his black beauty and thank it for being so good to me tonight. I kissed his cock and licked it up and down and around his cock head. I licked his clean hairless balls and let his cock rub against my face. He asked me if I enjoyed his black cock tonight. Did I like what he did to his white sissy fag? OH YES<<< OH YES.....I whispered in a heavy voice as I licked his cock and played with his balls. He grabbed my head once again and put his cock in my mouth as far as he could before I gagged. Oh my, what a surprise that was. He pumped very slowly in my mouth and then pulled out and told me to close my mouth and eyes. I did and he peed all over my face and chest!!!! It seemed like eternity before he finally emptied his bladder all over me. I was so shocked I was speechless. I just sat there in the tub on my knees with water and his pee cascading all over the front of me. He got out of the shower, grabbed a towel and told me to stay there until he told me to move. He left the bathroom with me still in the tub and the water flowing over me. I put my hands on my face to wash off the remments of his urine and let the water cleanse me.....Then I heard the door slam! I turned off the water and grabbed a towel and looked out the bathroom door........he was gone.
I was exhausted as I took off my hose and released my poor cock. I dried off and as I walked into the bedroom to pour another glass of wine my cell phone rang. It was him. He told me that he leaving me in the tub without saying goodbye was his last surprise. He told me I was a great fuck and he really enjoyed doing all the things he did to me for me and him. He'll always remember his white sissy fag! Then hung up.
Ill never forget that night either...My sissy fantasy realized I put on lace top thi hi's, silky bikini panties and a silky nighty and climbed into bed tired yet so fulfilled and surprised at what I did to chalk up another wonderful sexual experience on my bucket list! As I drifted off to sleep, I could still feel his big black cock buried inside me....my ass was still twitching and yearning for more
7 years ago
