Unexpected Orgy - Not My Finest Moment
After finishing high school, I attended a prestigious southern university graduating with a double major in Finance and Chemistry. When I arrived down south, I was a k** in a candy store as I never seen so many blonde blue-eye women. Growing up in northern New Jersey, it was always dark hair, dark eyes Italian / Jewish American princesses. I was truly enjoying myself after the summer of fun with Tom ended fucking everything in sight in my dorm room.
After completing my degree, I returned to NJ with my girlfriend and started doing financial analyses for a small specialty investment firm in Manhattan. I liked my job but hated my immediate boss. I think he was always scared that I would replace him, and he made it very stressful. He also did not like that I had a good relationship with his boss, Rick – a senior partner as we had similar interests (sports, music, same university, etc.).
One day Rick asked if I wanted to attend an art exhibit on Friday evening in SOHO. It was his wife’s brother show; never having attended an opening, I agreed as my girlfriend was in London for three weeks on business.
After finishing up some late work, I arrived at the gallery around 7:30 and it is partially crowded. I soon see Rick’s wife Sarah. We met previously at company functions and always had a laugh. She would always say “if you breakup with that girlfriend, I have someone for you.” I get a glass of wine and we start going around the exhibit. As we are proceeding looking at the art and meeting others, someone taps me on my shoulder. It is Tom, my first gay experience from high school. We hug each and say how long it has been since with seen each other. I explain to Sarah that Tom and I are old high school friends - running track and endlessly playing video games. I explain that I have not seen him in over 6 years as we lost touch after graduation and his parents moved. Sarah says, “You two go ahead and catch-up”.
We step over in a corner and start talking about where we are and what we have been up to over the years. Tom is still tall lean but a little more effeminate than I recall. He graduated from a design school and was working for an interior design firm. We talk for about an hour and have a couple more glasses of wine. Suddenly, another guy comes behind Tom and says “so this is where you been hiding”. Tom introduces me to his friend Hank. He is tall, fit, very similar build to myself but with piercing green eyes and short dirty blond hair.
I tell Tom I need to catch my train back to NJ. We exchange phone numbers and then I say good-bye to Sarah, Rick and her brother thanking them for the invite. As I am leaving, Tom, Hank and an older guy (~45) are near the exit. Tom introduced him as Raffaele. He is a small about 5’6”. The three of us tower over him as we are all over 6 foot. He is a muscular Hispanic guy with a greased back black hair into a ponytail.
As we exit, I explain that I am headed to the subway then Penn Station to catch the 10:30 train home. They are walking in the same direction and say they are headed to Raffaele’s place. As we approach my subway station, Tom ask me if I want to come for a night cap – “it is early and it is only 2 more blocks.” Feeling good from the wine and not having eaten all day – I say yes.
We get to the building. It is about 30 stories and the doorman greets Raffaele as we enter the lobby. We get on the elevator with five other people. It is crowded. I get in the left corner with Raffaele on right and Tom on the left. As we proceed up, I feel Tom touching my leg, I smile and he then slides his hand to my crotch. I then feel Raffaele’s hand on my butt. I am feeling good so I go with the flow getting slightly aroused on the ride up thinking I have not been with a guy in a long time. Little did I know what was coming my way:) I never have been in threesome - forget about a foursome. I am nervous but anxious heart beat racing and breathing slightly heavier as we get off.
We get off on the 24th floor while the other passengers continue upward. As we get off, it is strange to me as there is only a small hallway with two doors side by side for such a large building. As we enter the door on the left, it is a large room with floor to ceiling windows, a central sofa and tiny balcony with a view between buildings of New Jersey. I say something stupid about the view and Tom asks me to help him get some drinks. I follow Tom to the left of where we entered; there is a railroad kitchen with a small table at the end and another great view of the city. Tom asks me what I would like – I say wine but they do not have white. He says how about a gin and tonic. I reply “that’s good.”
As Tom is about to hand me my drink he leans in and kisses me. I kiss back. As I am feeling good, I am getting aroused which I think he realizes as he presses harder against me grabbing my ass. I soon feel his hand on my crotch and he says, “Just like I remember.” I move my right-hand down to his crotch. Just then, I see Hank out the corner of my eye. He comes over without saying a word and kisses me then Tom. He has very soft lips and now all three of us are kissing and rubbing. I was totally aroused. Hank then feeds me a little of my drink. He then un-buttons my shirt and pulls my t-shirt over my head. He starts biting my nipples. I feel my cock straining and just then Tom is taking down my pants and underwear. My erect cock pops out of my black Calvin Klein bikini briefs and Tom takes it in his mouth as I kiss Hank. I reach over with my left-hand and grope Hank’s crotch feeling that he is also aroused. I feel myself getting light-headed. Just then Raffaele appears and says, “let’s go to the playroom.”
Just then I realize that I am the only one without clothes. Hank starts walking away and Tom stands up. I see my pre-cum glistening on his lips. I kiss him and pull his shirt off. I grab his ass as we walk down a hallway with about five doors. Raffaele, Tom, me and then Hank enters the room in that order. There are floor to ceiling windows on two sides of the room with a great view of the city and mirrors on one wall with small track lighting above it. The room is large square 20’ x 20’. Except near the doorway, the entire room is a leather / vinyl bed with large triangular shaped pillows. In the corner near the mirrored wall is a stand with lube, condoms and various toys. Suddenly, I get nervous thinking everyone could be see me through these windows and what did I get myself into.
I take another sip of my drink. Tom then starts kissing me again and I could feel Hank’s hands on me, as I am still aroused. My inhibitions go away but I am very light headed. Tom is sandwiched between Hank and I. As Tom, Hank and I are playing I have no clue about Raffaele. I eventually pull off Tom pants and Tom pulls off Hank clothes. I am actually very aroused as I see that Tom and Hank are completely shaven – both very smooth (no stubble) as I feel their cocks and balls as we kiss. I have a small patch of neatly trim public hairs. We kiss each other and then I bend over gently to suck on Hank’s 5” cock and play with Tom’s. Hank’s cock is so smooth, very silky and tastes fruity and salty at the same time. Hank repositions one of the triangle pillows and pushes Tom over it. I start kissing Hank, he stops and grabs a condom as I grab my drink and gulp it down, as I am hot and sweaty with my heart racing. Tom is bent over the pillow with his ass in the air. Hank lubes up and slides into Tom very quickly. Tom’s eyes roll back in his eye in total pleasure. I bend over and kiss Tom and reach for his cock. I am now very lighted head, dizzy and weak almost passing out with my face on the bed and my ass in the air. I have no concept of time or place.
As I am lying prone, I feel hands on me and feel a pillow sliding under my belly. I think I am feeling more than one set of hands but whom. My head is turned to the right and I can see Hank working on Tom. I remember Tom smiling at me. I feel kisses on my ass and hands on my cheeks just then I feel a tongue on my asshole. It was incredible as I felt everything and chills ran through my body. I never had anyone eat my ass but I am there helpless (aware but very weak). I am enjoying the waves of pleasures that come over me. Just then, I feel fingers and cold lube being applied to my anus then a strange cool hard object entering me slowly. I tried to turn around to look but cannot get a good view. I feel slow even pressure in and out and I am breathing very heavy. I see Hank pulling his condom off and Tom lying over the pillow smiling at me.
Just then I feel two sets of hand on me rotating me around ass up on the edge of the triangle pillow. There is Raffaele straight between my legs and there is another guy to my right. I have no clue who he is. Both are naked. Raffaele is very muscular with a full arm tattoo; just then I see his cock. He is wearing a thick metal cockring and he is fully erect and enormous. It is the largest cock I have ever seen – like 12” and thick as a soda can. I had Tom’s 9” in the past but this is way bigger and thicker. I am thinking, “oh god I cannot take that” and where has he been hiding it. I am lying there in a dazed state. The mystery man is also dark hair muscular with three star tattoos on each his arm and abdomen each smaller star small in size then the next but unlike Raffaele his dick is tiny 3-4 inches at best.
The mystery man feeds me a drink, as I am all sweaty and positioned between two triangle pillows – like a cradle. Just then mystery man reaches around my ass and plays with the toy in my ass. He pulls it out. It is a 4-6” butt plug. Very strange feelings are waving over me – I have very heightened sensitivity – very aware but helpless. I feel everything. I then notice Raffaele reaching for another toy on the table – it is large clear blue conical shaped, ribbed dildo. He lubes it up and slowly slides it into me and starts moving very rhythmically. I feel pressure and some discomfort but no pain. Suddenly Raffaele pulls the dildo out of me and edges forward with his now condom covered cock, like I said I am aware but helpless; he lubes himself then slides into me slowly. I feel a lot of pressure then pain, it hurts but the pain subsides. I am thinking he has done this before with the ease he entered me. As he starts thrusting, I get fully erect. I start feeling waves of pleasure, breathing heavy and moaning. I am enjoying it. Mystery man is now playing with my cock and as I begin to leak pre-cum, he starts sucking me. My head is so sensitive I cum quickly all over my stomach. He keeps playing with my cum covered cock and I ejaculate again. I am feeling everything. He then moves his cock to my face and I begin to suck him. I hear him telling Raffaele “fuck that ass, oh yeah” which he repeated a couple of times. Raffaele is pumping faster and faster and I feel so much pressure and now discomfort. Just then, Raffaele stops and pulls out. I feel relieved and a sense of ease comes over me. I am breathing very heavily and panting. He starts to lose his erection and I see the condom full of semen as he rips it off. Just then, mystery man is masturbating over me and ejaculates over my chest with repeated sprays.
I am lying there groggy and helpless but feeling the warmth of the cum on me. I think I am dreaming going in and out of it. I then hear moans and groans coming from my right side but I do not recognize the voices. I turn my head in my dazed state and see a slim black guy with jockstrap being fucked by another black guy and another gray hair couple next to them – I am thinking - four more people - where did everyone come from? Just then Tom feeds me a drink from a water bottle. That is the last thing I totally remember.
The sun starts to rise and I wake up in the playroom near the corner table. My watch says 5:05. I see Tom and the black guy in the room but no one else. All three of us are naked. It is very quiet. The room smells of alcohol and sweat – like a bad gym locker. I see used condoms and toys s**ttered around the room. I sit up knowing I need to clean myself up and find my clothes. I go down the hallway and see no one. I open the first door looking for the bathroom but it is completely empty, no furniture just a bare room. I find the bathroom at the second door. I see myself in the mirror – my eyes are blood shot and I have dried cum everywhere in my hair, face, chest and legs. I hop into the full size glass shower to clean myself. As I am showering, I realize it is very strange only towels, soap, body wash and shampoo – no personal items – I see a couple of condoms in the waste basket. It is strange and eerie.
I finish quickly and go to the kitchen looking for my clothes. No one in sight – an empty apartment. Strangely my clothes are neatly folded on the small table; however, I cannot find my underwear. I get dress without them and leave feeling very odd, slightly embarrassed and self-conscious. I get downstairs to the lobby, nod at the doorman and flag a cab to Penn Station. Sitting there in the cab then train trying to recall everything but I can only recall pieces. I arrive home at around 7AM and my girlfriend calls from London asking me about the exhibit – I tell her “nothing special – a lot of mingling and chit chat with a few glasses of wine.” I then go soak in the tub and take another shower. I have a lot of intestinal discomfort and gas; I could not go to the bathroom for two days.
The next Friday afternoon, I get a call from Tom. He starts to apologize and I tell him I cannot speak right now but will call him in an hour – I wanted to collect my thoughts. I call him back in a more private area. He apologizes for not warning me. I explained I was willing but did not appreciate the d**gs – he said it was a herbal stimulant to put you at ease but I drank too much alcohol. I explained Raffaele eating my ass was exhilarating. I replied I was enjoying myself until the mystery man and that I did not enjoy being used by people I never met or even how many as I had no clue – no fucking recall. “It was not cool.” He is suddenly silent, nothing spoken for a number of seconds and then he invited me to that night’s event – I just hung up and never spoke to him again. I did however run into Hank in Fort Wayne, Indiana seven months later.
After completing my degree, I returned to NJ with my girlfriend and started doing financial analyses for a small specialty investment firm in Manhattan. I liked my job but hated my immediate boss. I think he was always scared that I would replace him, and he made it very stressful. He also did not like that I had a good relationship with his boss, Rick – a senior partner as we had similar interests (sports, music, same university, etc.).
One day Rick asked if I wanted to attend an art exhibit on Friday evening in SOHO. It was his wife’s brother show; never having attended an opening, I agreed as my girlfriend was in London for three weeks on business.
After finishing up some late work, I arrived at the gallery around 7:30 and it is partially crowded. I soon see Rick’s wife Sarah. We met previously at company functions and always had a laugh. She would always say “if you breakup with that girlfriend, I have someone for you.” I get a glass of wine and we start going around the exhibit. As we are proceeding looking at the art and meeting others, someone taps me on my shoulder. It is Tom, my first gay experience from high school. We hug each and say how long it has been since with seen each other. I explain to Sarah that Tom and I are old high school friends - running track and endlessly playing video games. I explain that I have not seen him in over 6 years as we lost touch after graduation and his parents moved. Sarah says, “You two go ahead and catch-up”.
We step over in a corner and start talking about where we are and what we have been up to over the years. Tom is still tall lean but a little more effeminate than I recall. He graduated from a design school and was working for an interior design firm. We talk for about an hour and have a couple more glasses of wine. Suddenly, another guy comes behind Tom and says “so this is where you been hiding”. Tom introduces me to his friend Hank. He is tall, fit, very similar build to myself but with piercing green eyes and short dirty blond hair.
I tell Tom I need to catch my train back to NJ. We exchange phone numbers and then I say good-bye to Sarah, Rick and her brother thanking them for the invite. As I am leaving, Tom, Hank and an older guy (~45) are near the exit. Tom introduced him as Raffaele. He is a small about 5’6”. The three of us tower over him as we are all over 6 foot. He is a muscular Hispanic guy with a greased back black hair into a ponytail.
As we exit, I explain that I am headed to the subway then Penn Station to catch the 10:30 train home. They are walking in the same direction and say they are headed to Raffaele’s place. As we approach my subway station, Tom ask me if I want to come for a night cap – “it is early and it is only 2 more blocks.” Feeling good from the wine and not having eaten all day – I say yes.
We get to the building. It is about 30 stories and the doorman greets Raffaele as we enter the lobby. We get on the elevator with five other people. It is crowded. I get in the left corner with Raffaele on right and Tom on the left. As we proceed up, I feel Tom touching my leg, I smile and he then slides his hand to my crotch. I then feel Raffaele’s hand on my butt. I am feeling good so I go with the flow getting slightly aroused on the ride up thinking I have not been with a guy in a long time. Little did I know what was coming my way:) I never have been in threesome - forget about a foursome. I am nervous but anxious heart beat racing and breathing slightly heavier as we get off.
We get off on the 24th floor while the other passengers continue upward. As we get off, it is strange to me as there is only a small hallway with two doors side by side for such a large building. As we enter the door on the left, it is a large room with floor to ceiling windows, a central sofa and tiny balcony with a view between buildings of New Jersey. I say something stupid about the view and Tom asks me to help him get some drinks. I follow Tom to the left of where we entered; there is a railroad kitchen with a small table at the end and another great view of the city. Tom asks me what I would like – I say wine but they do not have white. He says how about a gin and tonic. I reply “that’s good.”
As Tom is about to hand me my drink he leans in and kisses me. I kiss back. As I am feeling good, I am getting aroused which I think he realizes as he presses harder against me grabbing my ass. I soon feel his hand on my crotch and he says, “Just like I remember.” I move my right-hand down to his crotch. Just then, I see Hank out the corner of my eye. He comes over without saying a word and kisses me then Tom. He has very soft lips and now all three of us are kissing and rubbing. I was totally aroused. Hank then feeds me a little of my drink. He then un-buttons my shirt and pulls my t-shirt over my head. He starts biting my nipples. I feel my cock straining and just then Tom is taking down my pants and underwear. My erect cock pops out of my black Calvin Klein bikini briefs and Tom takes it in his mouth as I kiss Hank. I reach over with my left-hand and grope Hank’s crotch feeling that he is also aroused. I feel myself getting light-headed. Just then Raffaele appears and says, “let’s go to the playroom.”
Just then I realize that I am the only one without clothes. Hank starts walking away and Tom stands up. I see my pre-cum glistening on his lips. I kiss him and pull his shirt off. I grab his ass as we walk down a hallway with about five doors. Raffaele, Tom, me and then Hank enters the room in that order. There are floor to ceiling windows on two sides of the room with a great view of the city and mirrors on one wall with small track lighting above it. The room is large square 20’ x 20’. Except near the doorway, the entire room is a leather / vinyl bed with large triangular shaped pillows. In the corner near the mirrored wall is a stand with lube, condoms and various toys. Suddenly, I get nervous thinking everyone could be see me through these windows and what did I get myself into.
I take another sip of my drink. Tom then starts kissing me again and I could feel Hank’s hands on me, as I am still aroused. My inhibitions go away but I am very light headed. Tom is sandwiched between Hank and I. As Tom, Hank and I are playing I have no clue about Raffaele. I eventually pull off Tom pants and Tom pulls off Hank clothes. I am actually very aroused as I see that Tom and Hank are completely shaven – both very smooth (no stubble) as I feel their cocks and balls as we kiss. I have a small patch of neatly trim public hairs. We kiss each other and then I bend over gently to suck on Hank’s 5” cock and play with Tom’s. Hank’s cock is so smooth, very silky and tastes fruity and salty at the same time. Hank repositions one of the triangle pillows and pushes Tom over it. I start kissing Hank, he stops and grabs a condom as I grab my drink and gulp it down, as I am hot and sweaty with my heart racing. Tom is bent over the pillow with his ass in the air. Hank lubes up and slides into Tom very quickly. Tom’s eyes roll back in his eye in total pleasure. I bend over and kiss Tom and reach for his cock. I am now very lighted head, dizzy and weak almost passing out with my face on the bed and my ass in the air. I have no concept of time or place.
As I am lying prone, I feel hands on me and feel a pillow sliding under my belly. I think I am feeling more than one set of hands but whom. My head is turned to the right and I can see Hank working on Tom. I remember Tom smiling at me. I feel kisses on my ass and hands on my cheeks just then I feel a tongue on my asshole. It was incredible as I felt everything and chills ran through my body. I never had anyone eat my ass but I am there helpless (aware but very weak). I am enjoying the waves of pleasures that come over me. Just then, I feel fingers and cold lube being applied to my anus then a strange cool hard object entering me slowly. I tried to turn around to look but cannot get a good view. I feel slow even pressure in and out and I am breathing very heavy. I see Hank pulling his condom off and Tom lying over the pillow smiling at me.
Just then I feel two sets of hand on me rotating me around ass up on the edge of the triangle pillow. There is Raffaele straight between my legs and there is another guy to my right. I have no clue who he is. Both are naked. Raffaele is very muscular with a full arm tattoo; just then I see his cock. He is wearing a thick metal cockring and he is fully erect and enormous. It is the largest cock I have ever seen – like 12” and thick as a soda can. I had Tom’s 9” in the past but this is way bigger and thicker. I am thinking, “oh god I cannot take that” and where has he been hiding it. I am lying there in a dazed state. The mystery man is also dark hair muscular with three star tattoos on each his arm and abdomen each smaller star small in size then the next but unlike Raffaele his dick is tiny 3-4 inches at best.
The mystery man feeds me a drink, as I am all sweaty and positioned between two triangle pillows – like a cradle. Just then mystery man reaches around my ass and plays with the toy in my ass. He pulls it out. It is a 4-6” butt plug. Very strange feelings are waving over me – I have very heightened sensitivity – very aware but helpless. I feel everything. I then notice Raffaele reaching for another toy on the table – it is large clear blue conical shaped, ribbed dildo. He lubes it up and slowly slides it into me and starts moving very rhythmically. I feel pressure and some discomfort but no pain. Suddenly Raffaele pulls the dildo out of me and edges forward with his now condom covered cock, like I said I am aware but helpless; he lubes himself then slides into me slowly. I feel a lot of pressure then pain, it hurts but the pain subsides. I am thinking he has done this before with the ease he entered me. As he starts thrusting, I get fully erect. I start feeling waves of pleasure, breathing heavy and moaning. I am enjoying it. Mystery man is now playing with my cock and as I begin to leak pre-cum, he starts sucking me. My head is so sensitive I cum quickly all over my stomach. He keeps playing with my cum covered cock and I ejaculate again. I am feeling everything. He then moves his cock to my face and I begin to suck him. I hear him telling Raffaele “fuck that ass, oh yeah” which he repeated a couple of times. Raffaele is pumping faster and faster and I feel so much pressure and now discomfort. Just then, Raffaele stops and pulls out. I feel relieved and a sense of ease comes over me. I am breathing very heavily and panting. He starts to lose his erection and I see the condom full of semen as he rips it off. Just then, mystery man is masturbating over me and ejaculates over my chest with repeated sprays.
I am lying there groggy and helpless but feeling the warmth of the cum on me. I think I am dreaming going in and out of it. I then hear moans and groans coming from my right side but I do not recognize the voices. I turn my head in my dazed state and see a slim black guy with jockstrap being fucked by another black guy and another gray hair couple next to them – I am thinking - four more people - where did everyone come from? Just then Tom feeds me a drink from a water bottle. That is the last thing I totally remember.
The sun starts to rise and I wake up in the playroom near the corner table. My watch says 5:05. I see Tom and the black guy in the room but no one else. All three of us are naked. It is very quiet. The room smells of alcohol and sweat – like a bad gym locker. I see used condoms and toys s**ttered around the room. I sit up knowing I need to clean myself up and find my clothes. I go down the hallway and see no one. I open the first door looking for the bathroom but it is completely empty, no furniture just a bare room. I find the bathroom at the second door. I see myself in the mirror – my eyes are blood shot and I have dried cum everywhere in my hair, face, chest and legs. I hop into the full size glass shower to clean myself. As I am showering, I realize it is very strange only towels, soap, body wash and shampoo – no personal items – I see a couple of condoms in the waste basket. It is strange and eerie.
I finish quickly and go to the kitchen looking for my clothes. No one in sight – an empty apartment. Strangely my clothes are neatly folded on the small table; however, I cannot find my underwear. I get dress without them and leave feeling very odd, slightly embarrassed and self-conscious. I get downstairs to the lobby, nod at the doorman and flag a cab to Penn Station. Sitting there in the cab then train trying to recall everything but I can only recall pieces. I arrive home at around 7AM and my girlfriend calls from London asking me about the exhibit – I tell her “nothing special – a lot of mingling and chit chat with a few glasses of wine.” I then go soak in the tub and take another shower. I have a lot of intestinal discomfort and gas; I could not go to the bathroom for two days.
The next Friday afternoon, I get a call from Tom. He starts to apologize and I tell him I cannot speak right now but will call him in an hour – I wanted to collect my thoughts. I call him back in a more private area. He apologizes for not warning me. I explained I was willing but did not appreciate the d**gs – he said it was a herbal stimulant to put you at ease but I drank too much alcohol. I explained Raffaele eating my ass was exhilarating. I replied I was enjoying myself until the mystery man and that I did not enjoy being used by people I never met or even how many as I had no clue – no fucking recall. “It was not cool.” He is suddenly silent, nothing spoken for a number of seconds and then he invited me to that night’s event – I just hung up and never spoke to him again. I did however run into Hank in Fort Wayne, Indiana seven months later.
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