Halloween 1989
Halloween time, for myself, was a time to dress up and be anyone I wanted to be. I liked the makeup, the costumes, getting into character, and being naughty! This time was different. First, I was going out of town on my own to meet up with my friend Darnell. Second, I had turned 18 just a few weeks prior and was living in a rundown one bedroom duplex on the east side of town with my girlfriend. She had to work that night but she helped me get ready.
That afternoon around 3:30pm, my girlfriend was helping me with my makeup and laying out my costume. She was very skilled with altering it to fit me perfectly and she did a fabulous job with my makeup. I was going as Pippi Long stockings this year. I had grown my blonde hair out for years and with the help of red dye...... I was no a fiery red head. She put long fake eyelashes on with dark eye liner to make my blue eyes "pop". She put on loads of makeup on my face to the point I wanted to fuck myself. She helped me with my wild red hair and used tons of hairspray to keep it in place.... you could of dropped a brick on my head and I wouldn't of felt it. Admittedly, I looked hot! Once finished, my girlfriend took off to work and I was left to getting dressed. I put on my girlfriend's bra with some inserts to give a busty appearance. I slipped the green and white striped top that fit so tight that it barely covered my fake breasts. I pulled my long white stockings, one up each leg to my lean firm thighs. Then I pulled up my "naughty" short skirt that was very short. I was to wear big white panties under the skirt but chose a more "appropriate themed" covering.....a tiny and very tight red thong that covered my small shriveled cock and bulbous ball sack with a thin line that went snuggly up between my firm pale white ass cheeks. I then laced up my black leather boots with rainbow straps. Once completed, I drove to Darnell's place.
I met Darnell back a few years ago when he briefly moved to my small town. We instantly connected in the music we liked listening to and playing video games. Sadly, he moved away shortly after he told me he was gay. I wanted to tell him about my bisexuality but chickened out. We had connected when my girlfriend and I went out of town and bumped into him at shopping mall. My girlfriend and I initially found it odd since he was in the lingerie section of a JC Penneys, but he quickly said it was for his girlfriend. While my girlfriend was trying something on, Darnell confessed it was for him and that he was a performer in a drag club. He showed me a few pictures in his wallet and he looked sexy with the heavy makeup and massive eyelashes. He had the lips for it since his were so big and puffy. It gave me a tingle in my pants and I felt my cock surge. We exchanged phone numbers and started talking. I would later imagine Darnell's drag face on my girlfriend as she rode me in bed and later pegged me with my legs up. It made my erections harder and my cum more explosive during climax.
Darnell convinced me to come see him perform at the club on Halloween. With my girlfriend working that night, it was an easy sell. As I drove up to Darnell's I found myself pulling the thong to one side and playing with my stiff 6.5" extra thick cut cock as I sped along. I came close to climax but resisted the final few tugs. I stepped out of my car and positioned my swollen cock and balls into the tight red thong and adjusted the strap into the crack of my ass cheeks. I rang the doorbell and was greeted by a hulking figure. He was the most impressive manly specimen I'd ever seen. His muscles were bulging through his tight white top and his legs looked like tree trunks as they made his shorts stretch. His cock, though soft, could easily be made out and was much bigger than mine when hard. I was physically intimidated and it made my balls and cock shrink. I must of been staring too long when I heard the man speak. He introduced himself and I did in turn. He was very welcoming and let me in. He complimented my costume and if it hadn't been for all the makeup, he would of seen me blush. Initially, I was heartbroken but after talking with him as Darnell was still getting ready.... I actually was happy for Darnell. He told me how they met at the club and now considered a dedicated couple. Darnell came down with his makeup face and carrying his costume. He squealed with joy at my appearance and gave me a gentle hug as not to smear our makeup. We jumped into Darnell's partner's car and drove to the club. Darnell was impressed with my makeup and I admitted..... I had help. As we rode along, Darnell told his partner that I was his first crush and was the first person he told about being gay. On this truth, "high", I told him that I wanted to tell him about being bisexual. His partner exclaimed how thankful he was that I didn't since he was madly in love with Darnell. They blew kisses to each other and I felt like a third wheel but I was happy for them. It got quiet for an odd minute then his partner said if he wasn't with Darnell that he'd "fuck me raw". I instantly shifted as my cock grew into the tight red thong, my legs quivered and my ass got sweaty imagining this b**st of a man plowing me. I let out a faint gasp. Darnell joked warning me to stay away from his man. We all laughed.
Once there, Darnell went backstage to get in costume. His partner and I went to the bar. He offered to buy me a drink but I passed thinking of the drive home later that night. Initially I told my girlfriend that I might stay at Darnell's place but now that wasn't going to go as planned. When the show started, Darnell's partner and I moved up close to the stage. The music was loud as the first act was up. The crowd, though small, was loud and crazy as the first act lip sang the music. The crowd was mixed and it was difficult to make out if someone was a male or female due to the crossdressing. The vibe was electric and the dancing was infectious. I moved in ways I'd never done before. I liked my costume and something sexy in me was coming out. The next few acts were comical and had everyone roaring with laughter. I got noticed by a Cher look a like and as "she" talked about me a spot light shown down on me. I played along and enjoyed the fun barbs thrown my way. Everyone was cool and several compliments were thrown my way. I guess many though I was a girl and that only made me warmer. Then Darnell came on. He looked like Whitney Houston and did a marvelous job performing. His partner and I were his loudest supporters. In the finale, everyone came out and sang "it's raining men". As the song played again and again the performers came down off stage. I congratulated Darnell. He hugged me and thanked me. Then he was taken away by his partner. I was just bouncing around when the Cher look a like appeared in front of me. She thanked me for being a good sport and I told her how fun her act was. We were yelling into each other's ears since the music was so loud and the floor was crowded. We danced together and then......
Cher was circling me and placed a firm hand on my bare ass cheek. I jumped up and smiled. Cher smiled. We danced closer as the music played on. I was sweating. Cher seemed to be cool as a cucumber. She moved behind me and held me close rubbing herself against me. I had stared noticing that people were engaging in sexual activities. There was one couple already fucking over a table, there was one girl, who was dressed up as a guy, taking turns on two guys cocks. I felt my thong being slipped down my legs as I noticed Darnell was sitting on his partners lap kissing and probably fucking as well. It was an orgy!
I stepped out of my red thong and it was the last time I would be seeing it. I was leaned up against the bar with my ass out as Cher had pulled out a long slender missile like projectile from her dress. It was rubbed up between my sweaty pale white ass cheeks. It grew in length and I felt hardness. I rubbed my hind end up against her. The sexual toxicity was too much and I gave into my carnal desires. I was fucked while deafening music played on. I gave into the pulsating sounds and motion. I moaned loudly but no one could hear. Cher pumped deeper and deeper. Contents were shared up into my throbbing hole. Pain, pleasure.....it was a mixture of feeling both. My ass was in anguish as Cher withdrew. I felt sweat and seamen seeping out and down my legs. I slumped over the bar with my ass sticking out. When I looked for Cher, she was gone. I looked around but didn't see her. I staggered to a small table off and sat down on the sticky chair. I couldn't control the fluids escaping me. I took a drink of something as I was parched. As I downed the cool bitter beverage, a Grace Jones look a like sat down next to me. She asked how her drink tasted, I was startled. She quickly laughed it off. I was relieved since she was much tougher looking than I was and taller. She leaned over and put her hand on my thigh. She rubbed up and played with me as I saw her pull out a long thick sword like object from under her warrior furs. I swallowed hard. She pulled me down onto her log and I was struggling to wrap my mouth around. I was forced down and even the I resisted and gagged. No one noticed as I was made to mouth massage Grace's large appendage. Once she was satisfied, I was lifted ans placed on the table. My legs were opened up as I was given instructions to pull my leaky hole open. I was stretched and Grace was forced into me. Whatever clenching I had left in my tiny hole was over cum by this mass of flesh that entered me. I felt like it was in my throat as I looked in bewilderment this large thick black cock sliding up inside me. Grace was forced deeper into me. I cried out as loud as I could but the music drowned my scared and shockingly awed sounds. What gave me the most fright was when Grace went balls deep and I swear I saw my lower abdomen bulge. Another pump and it happened again. My cries turned to moans as the inner working of my body were being rearranged. Grace pulled out and white goo was ejaculated onto my abs and chest. My legs were sagging off the table, I collapsed back on the small table. The room was spinning as I looked in a haze at the other acts of debochry continued. I think even in all that crazy, I fell asleep for a moment as my body was overloaded with shock. When I awoke, I found my legs up over a Dolly Parton look a likes shoulders and a felt a smaller more manageable cock inside me. She took her time navigating deep into me. I grunted and moaned from the forceful slow pumps. She looked at me and I could only imagine how bad I looked with runny makeup on. My bra had been undone and then inserts gone. My shirt was now several feet away on the floor. My tiny skirt had been discarded somewhere as well. I found myself looking around as I was being barebacked by yet another stranger. Dolly finished with a sickening moan. My legs were numb and hurt when they were taken off shoulders. My body ached all over. My ass still craved for Grace Jones' cock. I sat up naked on the table and found Grace. She was fucking another bent over a chair. I stumbled over to her. I was groped and grabbed as I continued to move closer. Once there, I shouted as loud as I could into Grace's ear. "Please fuck me!" Grace looked down at my slender athletic frame and nodded. I bent over a table and spread my shaking legs. I Grace pull out her long thick shaft of an ass. The veiny muscle slipped out and hung heavy between her legs. She slapped it on my ass and lower back. I reached back and felt the life in her massive appendage. My body quivered and was in moments fulfilled with bbc! Grace pounded flesh deep into parts of me that had never been touched. My tears of pain were welcomed with a tasting of his cum as I sucked him dry swallowing every ounce of the hot salty essence of a man's cock. I begged for more......
That afternoon around 3:30pm, my girlfriend was helping me with my makeup and laying out my costume. She was very skilled with altering it to fit me perfectly and she did a fabulous job with my makeup. I was going as Pippi Long stockings this year. I had grown my blonde hair out for years and with the help of red dye...... I was no a fiery red head. She put long fake eyelashes on with dark eye liner to make my blue eyes "pop". She put on loads of makeup on my face to the point I wanted to fuck myself. She helped me with my wild red hair and used tons of hairspray to keep it in place.... you could of dropped a brick on my head and I wouldn't of felt it. Admittedly, I looked hot! Once finished, my girlfriend took off to work and I was left to getting dressed. I put on my girlfriend's bra with some inserts to give a busty appearance. I slipped the green and white striped top that fit so tight that it barely covered my fake breasts. I pulled my long white stockings, one up each leg to my lean firm thighs. Then I pulled up my "naughty" short skirt that was very short. I was to wear big white panties under the skirt but chose a more "appropriate themed" covering.....a tiny and very tight red thong that covered my small shriveled cock and bulbous ball sack with a thin line that went snuggly up between my firm pale white ass cheeks. I then laced up my black leather boots with rainbow straps. Once completed, I drove to Darnell's place.
I met Darnell back a few years ago when he briefly moved to my small town. We instantly connected in the music we liked listening to and playing video games. Sadly, he moved away shortly after he told me he was gay. I wanted to tell him about my bisexuality but chickened out. We had connected when my girlfriend and I went out of town and bumped into him at shopping mall. My girlfriend and I initially found it odd since he was in the lingerie section of a JC Penneys, but he quickly said it was for his girlfriend. While my girlfriend was trying something on, Darnell confessed it was for him and that he was a performer in a drag club. He showed me a few pictures in his wallet and he looked sexy with the heavy makeup and massive eyelashes. He had the lips for it since his were so big and puffy. It gave me a tingle in my pants and I felt my cock surge. We exchanged phone numbers and started talking. I would later imagine Darnell's drag face on my girlfriend as she rode me in bed and later pegged me with my legs up. It made my erections harder and my cum more explosive during climax.
Darnell convinced me to come see him perform at the club on Halloween. With my girlfriend working that night, it was an easy sell. As I drove up to Darnell's I found myself pulling the thong to one side and playing with my stiff 6.5" extra thick cut cock as I sped along. I came close to climax but resisted the final few tugs. I stepped out of my car and positioned my swollen cock and balls into the tight red thong and adjusted the strap into the crack of my ass cheeks. I rang the doorbell and was greeted by a hulking figure. He was the most impressive manly specimen I'd ever seen. His muscles were bulging through his tight white top and his legs looked like tree trunks as they made his shorts stretch. His cock, though soft, could easily be made out and was much bigger than mine when hard. I was physically intimidated and it made my balls and cock shrink. I must of been staring too long when I heard the man speak. He introduced himself and I did in turn. He was very welcoming and let me in. He complimented my costume and if it hadn't been for all the makeup, he would of seen me blush. Initially, I was heartbroken but after talking with him as Darnell was still getting ready.... I actually was happy for Darnell. He told me how they met at the club and now considered a dedicated couple. Darnell came down with his makeup face and carrying his costume. He squealed with joy at my appearance and gave me a gentle hug as not to smear our makeup. We jumped into Darnell's partner's car and drove to the club. Darnell was impressed with my makeup and I admitted..... I had help. As we rode along, Darnell told his partner that I was his first crush and was the first person he told about being gay. On this truth, "high", I told him that I wanted to tell him about being bisexual. His partner exclaimed how thankful he was that I didn't since he was madly in love with Darnell. They blew kisses to each other and I felt like a third wheel but I was happy for them. It got quiet for an odd minute then his partner said if he wasn't with Darnell that he'd "fuck me raw". I instantly shifted as my cock grew into the tight red thong, my legs quivered and my ass got sweaty imagining this b**st of a man plowing me. I let out a faint gasp. Darnell joked warning me to stay away from his man. We all laughed.
Once there, Darnell went backstage to get in costume. His partner and I went to the bar. He offered to buy me a drink but I passed thinking of the drive home later that night. Initially I told my girlfriend that I might stay at Darnell's place but now that wasn't going to go as planned. When the show started, Darnell's partner and I moved up close to the stage. The music was loud as the first act was up. The crowd, though small, was loud and crazy as the first act lip sang the music. The crowd was mixed and it was difficult to make out if someone was a male or female due to the crossdressing. The vibe was electric and the dancing was infectious. I moved in ways I'd never done before. I liked my costume and something sexy in me was coming out. The next few acts were comical and had everyone roaring with laughter. I got noticed by a Cher look a like and as "she" talked about me a spot light shown down on me. I played along and enjoyed the fun barbs thrown my way. Everyone was cool and several compliments were thrown my way. I guess many though I was a girl and that only made me warmer. Then Darnell came on. He looked like Whitney Houston and did a marvelous job performing. His partner and I were his loudest supporters. In the finale, everyone came out and sang "it's raining men". As the song played again and again the performers came down off stage. I congratulated Darnell. He hugged me and thanked me. Then he was taken away by his partner. I was just bouncing around when the Cher look a like appeared in front of me. She thanked me for being a good sport and I told her how fun her act was. We were yelling into each other's ears since the music was so loud and the floor was crowded. We danced together and then......
Cher was circling me and placed a firm hand on my bare ass cheek. I jumped up and smiled. Cher smiled. We danced closer as the music played on. I was sweating. Cher seemed to be cool as a cucumber. She moved behind me and held me close rubbing herself against me. I had stared noticing that people were engaging in sexual activities. There was one couple already fucking over a table, there was one girl, who was dressed up as a guy, taking turns on two guys cocks. I felt my thong being slipped down my legs as I noticed Darnell was sitting on his partners lap kissing and probably fucking as well. It was an orgy!
I stepped out of my red thong and it was the last time I would be seeing it. I was leaned up against the bar with my ass out as Cher had pulled out a long slender missile like projectile from her dress. It was rubbed up between my sweaty pale white ass cheeks. It grew in length and I felt hardness. I rubbed my hind end up against her. The sexual toxicity was too much and I gave into my carnal desires. I was fucked while deafening music played on. I gave into the pulsating sounds and motion. I moaned loudly but no one could hear. Cher pumped deeper and deeper. Contents were shared up into my throbbing hole. Pain, pleasure.....it was a mixture of feeling both. My ass was in anguish as Cher withdrew. I felt sweat and seamen seeping out and down my legs. I slumped over the bar with my ass sticking out. When I looked for Cher, she was gone. I looked around but didn't see her. I staggered to a small table off and sat down on the sticky chair. I couldn't control the fluids escaping me. I took a drink of something as I was parched. As I downed the cool bitter beverage, a Grace Jones look a like sat down next to me. She asked how her drink tasted, I was startled. She quickly laughed it off. I was relieved since she was much tougher looking than I was and taller. She leaned over and put her hand on my thigh. She rubbed up and played with me as I saw her pull out a long thick sword like object from under her warrior furs. I swallowed hard. She pulled me down onto her log and I was struggling to wrap my mouth around. I was forced down and even the I resisted and gagged. No one noticed as I was made to mouth massage Grace's large appendage. Once she was satisfied, I was lifted ans placed on the table. My legs were opened up as I was given instructions to pull my leaky hole open. I was stretched and Grace was forced into me. Whatever clenching I had left in my tiny hole was over cum by this mass of flesh that entered me. I felt like it was in my throat as I looked in bewilderment this large thick black cock sliding up inside me. Grace was forced deeper into me. I cried out as loud as I could but the music drowned my scared and shockingly awed sounds. What gave me the most fright was when Grace went balls deep and I swear I saw my lower abdomen bulge. Another pump and it happened again. My cries turned to moans as the inner working of my body were being rearranged. Grace pulled out and white goo was ejaculated onto my abs and chest. My legs were sagging off the table, I collapsed back on the small table. The room was spinning as I looked in a haze at the other acts of debochry continued. I think even in all that crazy, I fell asleep for a moment as my body was overloaded with shock. When I awoke, I found my legs up over a Dolly Parton look a likes shoulders and a felt a smaller more manageable cock inside me. She took her time navigating deep into me. I grunted and moaned from the forceful slow pumps. She looked at me and I could only imagine how bad I looked with runny makeup on. My bra had been undone and then inserts gone. My shirt was now several feet away on the floor. My tiny skirt had been discarded somewhere as well. I found myself looking around as I was being barebacked by yet another stranger. Dolly finished with a sickening moan. My legs were numb and hurt when they were taken off shoulders. My body ached all over. My ass still craved for Grace Jones' cock. I sat up naked on the table and found Grace. She was fucking another bent over a chair. I stumbled over to her. I was groped and grabbed as I continued to move closer. Once there, I shouted as loud as I could into Grace's ear. "Please fuck me!" Grace looked down at my slender athletic frame and nodded. I bent over a table and spread my shaking legs. I Grace pull out her long thick shaft of an ass. The veiny muscle slipped out and hung heavy between her legs. She slapped it on my ass and lower back. I reached back and felt the life in her massive appendage. My body quivered and was in moments fulfilled with bbc! Grace pounded flesh deep into parts of me that had never been touched. My tears of pain were welcomed with a tasting of his cum as I sucked him dry swallowing every ounce of the hot salty essence of a man's cock. I begged for more......
1 year ago