Chapter 4: Awkward Gay Sexual Encounters
When I was 25 years old, I met Nessa, a stunningly attractive 29-year-old African American woman in an online chat room called Ebony Female for Ivory Male. She lived across the country from me and was the mother of two daughters. Despite the distance, she flew out to meet me, spending three unforgettable days together. We explored my town, enjoyed music and dancing at local bars, and I felt proud to be with her as an interracial couple.
Nessa’s curvy, voluptuous figure weighing 195 pounds at 5-foot 2-inches tall with 46 G Cup sized breasts that I genuinely enjoyed sucking on her large nipples when I held her in bed naked. I often held her beautifully enormous breasts and loved seeing them bounce and sway when we were having sex. She had a vibrant personality and made every moment we shared together emotionally and sexually special. We shared enthusiastic kisses and intimate moments in my queen-size bed, savoring the feeling of closeness and comfort as we made love with each other while having intimate sex. Her ass was large, but beautiful with a massive and deep butt crack that was very enjoyable fucking. I could see her ass bouncing while I fucked her doggy-style. Those three days filled with warmth, connection, and a sense of adventure that I still remember fondly. She was into both oral and vaginal sex with white men.
When I was 26 years old, Nessa convinced me to move across the country to share a three-bedroom apartment with her and her two African American daughters. Alisa was eight years old and Beth was nine when I first moved in. At first, all four of us got along very well, creating a comfortable and supportive household.
Nessa and I had an active sex life and had to lock the bedroom door to prevent her daughters from coming in our bedroom while we were having sex. Nessa loved giving me blowjobs. Nessa gave blowjobs in bed before I would fuck her. Nessa gave me a kinky blowjob, sucking me off while I was driving us to her brother’s trailer home in a trailer park. Nessa gave me a blowjob, sucking me off while her and I were sleeping on the living room floor of her sister’s house while we were visiting her in another state.
I loved fucking her both vaginally and anally. Nessa and I did vaginal sex most of thee time, mostly while she was on her back with her legs spread so I could deep kiss her while I was fucking Nessa and often sucking the large nipples of her 46 G cup breasts that I often rested my head on while we were sleeping. I loved lifting her feet over my shoulders while her legs were spread, at time to fuck her pussy deep with Nessa often screaming loudly while we came together. I loved fucking Nessa in the doggy-style position that we mostly did vaginally, and a few times did on Nessa anally when she got extra horny after we were drinking. I loved holding Nessa’s love handles created between the guts of her stomach and her legs that allowed me to grip the gap created and fuck her ass hard with my pelvis making a slapping sound each time I slammed against her ass while we fucked and had me excited as I came heavily in her ass and pussy each time I came when I fucked her doggy-style.
There were a number of times when Nessa would hold her 46 G cup breasts together for me to fuck her tits while I sat on her stomach and cumming on her face or in her mouth for her to swallow my cum. One night after we had been drinking Nessa tried something kinky and different with her head partially off the end of the bed so she could watch me fuck her tits over her head and then holding her head to face fuck her mouth and throat while she slobbered all over her face with her eyes enlarging and getting red as she gagged on my cock as I fucked her mouth and throat deep as she wanted, getting slobber and cum all over her face and hair when I came in her mouth.
After two years, our personal and sexual relationship began to deteriorate. The main reason was that I worked the opposite shift from her job, and our schedules hardly aligned with her and her daughters' school routines, making it difficult for us to spend quality time together.
When I was 28 years of age I had gone through 2 bad relationships with women and it was beginning to feel like I was stuck in another bad relationship with a 32-year-old African American Big Beautiful Black Woman who was beginning to make me feel sexually deprived from what had become a non-existent sex life. I had not had sexual encounters with men in 4 years since the last time I had sex with Corsica. After having moved across the country and having an extended drought of sexual activity with men and the woman I was living with. I decided it was time to try finding men on man for man gay chat rooms and making efforts to meet gay and bisexual men at a local gay bar. I was still in great shape, at 6 feet tall, and 155 pounds in weight with a 7-inch-thick cut cock that was beginning to be under used.
Sadly, a number of men I met in the gay chat rooms and at the local gay bar were sexually awkward experiences when meeting them either at their home or at the apartment I was sharing with Nessa and her daughters while Nessa’s daughters were away at school and after school activities that Nessa was often involved in, and while Nessa was at work out of town. I often did not know what I was getting into sexually with gay and bisexual men I would meet until meeting them.
I met Nathanial at his home after chatting with him on a man for man gay chat room. Nathanial was a 5-foot and 8-inches tall bisexual white man with brown hair and brown eyes, weighing 165 pounds. When I met Nathanial, he was drunk and naked when he met me at the door of his trailer home. Nathanial gave me a kiss when I met him at the door and went down on his knees to take my cock out of my pants and sucking my cock while his door was open and his neighbors were sitting outside their trailer home in chairs drinking beer as they watched Nathanial sucking my cock in his doorway until me cock was hard. When my cock was hard Nathanial got up and held my hand to lead me to his bedroom where we kissed as he undressed me before we both crawled into bed naked. We made out kissing each other before he turned over on his side with his back and ass facing me after spitting of his hand and rubbing his spit on his asshole to moisten it for his ass to be ready for me to fuck. Nathanial grinded his ass against my cock as I slid my cock deep inside his ass and slowly fucked Nathanial’s ass as he continued grinding his ass on my cock until I came deep inside his ass. I kept my cock deep inside Nathanial’s ass after cumming inside his ass and held his cock in my hand and kissing his ear and he passed out as we laid in bed and started snoring as I held him naked buried deep in his ass. After holding Nathanial for ten minutes with him snoring I got up to put my clothes on and left after he had passed out in bed naked after I fucked him.
The second awkward gay sexual experience was with a man I met at a local gay bar and his crossdressing roommate and gay boyfriend Aaron. After dancing with Micheal and kissing him on the dance floor while holding each other close to a slow song I gave him a ride to his home. Michael ‘s trailer home was in a trailer park, and he was living with a roommate that was a 60-year-old crossdresser, Aaron. Aaron was not attractive; he was six feet tall weighing 190 pounds with greyish brown hair and brown eyes with an eight-inch cock that was cut and thick as he was dressed in a female nightgown. Michael was a 25-year-old gay man who was 5-foot and 10-inches tall with black hair and brown eyes and a medium build weighing 160 pounds with a cock that was 7-inches, cut and thick. When Michael welcomed me into his home in the trailer his roommate Aaron was wearing makeup and a women’s exotic nightgown as he sat in the living room watching gay sex porn on the television. Michael and I said hello, and I introduced myself to Aaron to him as we passed while we went back to Michael's bedroom. Michael and I made out and kissed as we undressed each other and crawled into bed naked to continue making love to each other while we were making out in his bed. Michael and I switched sides of the bed and laid facing each other in the sixty-nine position and began sucking each other’s cocks when his cross-dressing roommate Aaron came into the bedroom with a beer and sat in a chair by the bed to watch us sucking each other’s cocks. I stopped sucking Michael's cock as Michael continued sucking mine and asked his cross-dressing roommate Aaron, “What are you doing in the bedroom, I cannot remember Michael or I invite you into the room to join or observe us having gay sex with each other.” Michael’s cross-dressing roommate Aaron responded saying, “Tony, I did not need to sit in the living room watching gay porn when I can to come in the bedroom to watch a live gay porn in a bedroom I share with Michael as a gay couple. Michael and I have an open gay relationship where either of us can have sex with other men if the other is able to sit back and watch them having sex with other men and join in on having sex with them.
I watched the crossdresser Aaron masturbating while I began eating at Michael’s asshole to get his ass moist, so it was ready for me to fuck. I fingered Michael's asshole with comfort and rolled Michael over on his stomach to slid my cock deep into his ass. I fucked Micheal’s deep in his ass as we held hands with our fingers interlocked as I kissed him while his head was turned towards me. Michael's crossdressing roommate Aaron took his clothes off as Michael and I were making love. The crossdresser Aaron sat on the bed and started fondling my ass as I was fucking Michael deep in his ass when the crossdresser Aaron said, “I need to get some of Tony’s beautiful ass,” as he spit on his hand and rubbed it in my asshole to make it wet and began fingerbanging my asshole with his middle finger as he stroked his cock to make it hard. When Aaron, the crossdresser’s cock was hard, he said, “Since you are fucking my boyfriend it is my turn to fuck you, Tony. Your ass is as beautiful as my boyfriends, and I want to take part of it since you are fucking my gay boyfriend and lover.” Crossdresser Aaron laid on top of me and held his boyfriend on the bottom of the pile of three gay men as he slid his cock into my ass and began fucking me deep and slow as Michael and my hand and fingers interlocked as we continued kissing. The feeling of Aaron, the crossdresser’s cock deep in my ass slow fucking me while kissing my neck made my cock explode deep inside Michael's ass and made him moan as he had felt me cumming inside his ass. Michael began moaning loudly as the crossdresser Aaron started fucking my ass hard and deep after I came deep in Michael's ass. I had already cum inside Michael's ass and Micheal told me, “Tony, keep your cock inside my ass, this feels so good having your cock deep in my ass while my roommate is fucking your ass deep and hard. It is making me cum on the bed below me. I am loving this.” Shortly afterwards I could feel the crossdresser Aaron’s cum deep inside my ass as he moaned with sexual pleasure holding us both tight until he was finished cumming deep inside my ass. The crossdresser Aaron got up and sat in the chair by the bed and said to me, “Okay Tony, I am finished, so you can go home.”
I looked at Aaron while my cock was still buried in Micheal’s ass and said, “Are you serious.”
Michael looked at me and said, “Unfortunately, yes Tony, Aaron is. Aaron and I have been a gay couple for five years and I only bring men here to our bedroom to fuck me while my boyfriend fucks them as they are fucking me. I do it because it feels so good having another man’s cock inside my ass and my gay lover Aaron is fucking them while their cock is still deep inside my ass. It made it feel like my boyfriend Aaron was fucking me while he was fucking you while my ass filled with cum Tony.”
After that I felt like suck a cheap and easy anal whore after I put on my clothes and left to go home. I could feel my underwear getting wet as the cum was dripping out of my ass as I drove.
The third awkward gay sexual experience and first of the men that came and met me at my apartment to have gay sex with me was Jonathan who I met in the man for man gay chat room. Jonathon came over and made out with me as we took each other’s clothes off and took a shower together. Jonathon and I made out with each other in the shower as we washed each other off before Jonathan got down on his knees and gave me a deepthroated blowjob while we were in the shower. I came in Jonathon’s throat, and he swallowed cum before he got up and gave me a kiss as he dried himself with a towel and got dressed and left the apartment while I was still naked without me seeing or hearing from him again afterwards. It felt like the only reason he came and gave me a blowjob was an exchange for a shower.
The fourth awkward gay sexual experience and second man I met at the apartment for gay sex was Juan, a 20-year-old gay Mexican American who was a sissy gay bottom. Juan was a slender gay sissy man who was 5 foot 6 inches tall with dark hair and brown eyes weighing 130 pounds with a cock that was 6 inches cut and thick. Juan was into intimacy and we made out while undressing to take a shower together. While we were in the shower Juan got down on his knees and gave me a blowjob until my cock was hard when he used hair conditioner to lubricate his ass and asked me to fuck him as he held the wall by the showerhead. Juan held my cock behind him as he worked it deep into his ass and I fucked him hard, deep, and fast until I came deep inside his ass as he moaned with joy and pleasure until I finished cumming deep inside his ass. After I came deep inside his ass, Juan gave me a kiss and we washed each other off. Juan turned off the shower and held me giving me a deep and passionate kiss as he took hold of my cock and stroked it as we kissed until my cock was hard when he got down and kissed the head of my cock and stood back up holding me and my cock close. Juan gave me a deep passionate kiss before he looked into my eyes with a horny and passionate look and said, “Ok Tony, I am ready for you to go with me to your bed and fuck the shit out of my ass while I am on my stomach and cum deep in my ass with your cock staying deep inside my ass until your finished cumming, then I want you to roll me over onto my back and fuck me the same way. I can feel cum inside my ass after you fucked my ass in the shower. As wonderful as your cock feels in my ass I want you to give me more and fill my ass so full of your sweet cum that I will feel it dripping from my ass all day Tony.”
I went to bed with Juan and he laid on his stomach; I stuck my cock deep into his ass lubricated with the cum that was dripping out after I fucked his ass in the shower. I fucked Juan hard and deep as he moaned as we kissed while his head turned towards me as we held each other’s hands tight above Jaun’s shoulders. I told Juan, “I am about to cum.”
Juan screamed with joy saying, “Your cock feels so good in my ass. I want you to stay deep inside my ass to fill my ass full of your semen. Do not pull your cock out to roll me over until you finish cumming in my ass Tony. I am loving it.” I stayed inside his ass with my cock for five minutes after I finished cumming inside his ass as we kissed. I regained my breath before rolling Juan over onto his back to fuck him again. I lifted Juan’s spread legs with his feet over my shoulders as I slid my cock deep into Juan’s cum filled ass and fucked him hard and deep while he held onto my arms. I leaned forward holding his shoulders and Juan investigated my face passionately and said, “I want you to fuck me so hard Tony that I will be walking with a wobble for days with cum dripping from my ass all day when you finish fucking my ass. I love your cock deep in my ass more than my boyfriend’s cock. Your cock feels so good in my ass.” My cock exploded with cum with all the sexual excitement I was feeling, and I laid on Juan’s stomach holding and kissing him as I finished cumming deep inside his ass.
When I finished cumming I looked into Juan’s eyes and asked him, “Why did you say my cock feels better in your ass than your boyfriend’s cock?” Juan gave me a kiss as he got up and put his clothes on while I was laying naked in bed and I asked him, “Are you sure you do not want to take a shower and clean yourself off before you leave Juan?”
After Juan finished putting his clothes on, he gave me a kiss as he was ready to leave while I was still laying naked in bed and said, “Thank you for filling my asshole with your cum Tony. I enjoyed making love with you as wonderful as your cock felt inside my ass. I brought up my boyfriend because I decided to cheat on him by letting you fuck me after I caught him fucking another man in our bed. I watched them fucking while I stood quietly in the hallway without my boyfriend knowing I was there. When I get home, I am going to put cum filled underwear under his pillow as a payback for fucking another man in our bed. When my boyfriend finds my underwear filled with cum stains from your cum dripping out of my ass, I am going to let him know I let you fuck me after I saw him fucking another man in our bed. I am going to tell him that if I ever catch him cheating on me with another man again, I will leave him and find another man to fuck me permanently as their gay boyfriend and lover instead of his boyfriend and lover.” I never heard from or saw Juan again after that. It felt weird knowing I became a gay cheater’s fuck toy as payback from an affair his boyfriend was having with another gay man in a gay couple’s relationship.
My fifth awkward gay sexual experience with a man was with Dan. Dan was the sixth gay man to hook up with me sexually and the third man I met for sex at my apartment after meeting and chatting with him on a man for man gay chat room. Having gay sex with Dan was not exciting. Dan was six feet tall, 180 pounds with an average build, blonde hair with hazel eyes as a bisexual man with a cock that was seven inches long, cut, and thick. Dan had a nice ass, and he liked having men fuck him in his ass. Dan only fucked women’s pussy when having sex with them and he was only into fucking women. When Dan came over to my apartment he did not do anything beyond giving me a hand job to get my cock hard while he lubed his asshole with KY Jelly after he brought his pants down for me to fuck him in the ass through the whole he had cut in the back of his underwear so he could be fucked without taking them off. After I came deep inside his ass he and just pulled up his pants and left when I finished fucking him while I was laying on the bed naked. As boring as our gay sexual encounter was, Dan and I never got together sexually again.
A month later I had my sixth awkward gay sexual experience after I met Greg on the gay man for man chat room. Greg became the seventh man I met with for a gay sexual encounter and the fourth man I had sex with at my apartment after I had gotten together with Nessa. Greg said he was into kinky gay sex. Greg told me he loved giving men blowjobs and prostate massages to give men an explosive orgasm. When I asked Greg what his physical stats were, he told me he was a sixty year old bald gay white man with brown eyes who was 6-feet tall and 175 pounds with an 8-inch cock and Greg told me he was versatile sexually with men because he was into both fucking men in the ass and having men fuck him in the ass.
Greg came to my apartment with a small duffle bag and I asked Greg, “What is in the duffle bag sexy.”
Greg told me, “It is a thick double ended 20-inch dildo with thick dick heads on both sides for sexual pleasure that I like to use when I am having sex with men so we can safely fuck each other’s asses while we can use together if you are interested. Do not worry, I have experience using it with other men so I will know what I am doing when I show you how it is used Tony.”
I gave Greg a kiss and held his hand as I led him to the bedroom he asked me, “Can you take off all your clothes, and to lay comfortably on your back.” I turned on the stereo in the bedroom and danced as I stripped and took my clothes off while Greg watched until I was naked and got into bed laying on my back like Greg had asked Greg told me, “You look sexy Tony, I cannot wait to make love to you.” Greg took his clothes off and he crawled into be with me while both of us were naked and Greg rubbed my chest and asked me, “Would it be ok for me to fingerfuck your ass you while I am giving you a blowjob?”
I told Greg, “I am ok with that Greg. You can do whatever you want with my ass and my cock while we are having gay sex together Greg. My entire body belongs to you while we are having gay sex together and I give you permission to use any part of my body any way you choose while having sex with me.” Greg lubed his index finger with KY Jelly, and he put it up my ass to massage my prostate as he gave me head. The prostate massage felt so good that my cock exploded in Greg’s mouth when I came and it made my entire body tingle and quiver when I came.
After Greg swallowed cum, he said, “Now it is time for us to use the dildo while I am giving you a blowjob to make you cum even more if I was ok with-it Tony.”
I told Greg he could and he lubed the dildo on both ends before he slowly slid the dildo up my ass while I was on my back and he started sucking my cock again. As Greg sucked my cock deep, he slowly moved the dildo up and down in my ass until I came deep in Greg’s throat. After Greg swallowed the cum, he told me, “Roll over Tony and get up onto your knees while the dildo is still in your ass so I can put the other end of the double ended dildo inside my ass so we can fuck each other with the double ended dildo to give each other gay anal sexual pleasure at the same time.” I got onto my hands and knees Greg got onto his knees behind me facing the other way and put the other end of the double headed dildo deep inside his ass with our knees touching as he straddled his ass to mine with the dildo up both of our asses as we moaned with sexual pleasure while rubbing our asses against each other’s asses with the twenty inch double ended dildo deep inside our asses until both of our cocks came shooting cum all over the bed sheets came onto the bed sheets as Greg and I gripped onto each other’s asses while we fucked ourselves in the ass together.
After Greg and I finished having sex, I asked Greg, “Why he uses a dildo to fuck rather than using your cock?”
Greg told me, “I like fucking and having my ass fucked at the same time, and the double ended dildo allows me to do so with other men while making it easier to clean up and go afterwards. At least I know that I cannot get any sexual diseases from a dildo for anal sex with men. I love fucking men in the ass using my own cock and having men fuck me in the ass with their cock to after I have been with another man for an extended period so we can both feel safe doing so sexually without condoms.” Greg put his clothes on and held my cock as he gave it a kiss before giving me a deep enthusiastic kiss mouth to mouth as a kiss goodbye while I was lying in bed naked. Before Greg left, he told me, “You are an incredibly attractive young man with a beautiful ass and a wonderful cock that any gay man would enjoy as much as I did while making love with you. I envy the sexual pleasure other gay men are going to have with you in the future because your openness to try gay sexual acts that are new to you makes having sex with you amazing Tony.”
As weird as it left me feeling in the awkward way Greg and I had man on man gay sex together it was exciting and sexually pleasing as kinky as it was. I would have enjoyed having fully man on man anal sex with Greg where we could have fucked each other with our own cocks and sucked each other off for oral pleasure, but Greg and I never got together to have sex again afterward and I did not catch him on the local man for man gay chat room again after that..
The next person I met on the man for man gay chatroom was Emanuel. Emanuel and I chatted with each other online for two weeks before he got us a motel room to meet and have gay sex together and he was the eight man I had gay sex with after I had moved in with Nessa and it was the first gay sexual experience that I had with a man after I had moved in with Nessa that did not become awkward. Emanuel was a Hispanic man I made love with romantic man on man gay sex as fucked me in my ass to breed me. Emanuel was 6 feet tall, 280 pounds with brown eyes and black hair with a large build and big sexy ass with a 7-inch cut and thick cock.
Emanuel made a hotel room reservation for us, and he told me that he was going to give me a full body massage that I would never forget. Emanuel left me feeling excited when I was left thinking about it all week after he discussed his sexual ideas he shared about what he wanted to do with me sexually.
Friday night as we were chatting in the man for man gay chat after Emanuel checked in to our hotel room and he let me know he checked in to the room after he got there. Emanuel provided me with the name of the hotel and the address and room number, and I took a shower and got dressed in shorts, a t-shirt, and sandals. I sent Emanual a message on the man for man gay chat that I was on my way to the hotel room he had given me to meet him.
To my surprise, when I got to the hotel room and knocked at the door, Emanuel answered the door to let me in while he was fully naked. Emanuel gave me a hug and a deep enthusiastic kiss while a man and a woman were in the hallway watching us. We kissed passionately for five minutes as the man and woman looked shocked to see a me kissing another man who was naked in the doorway as he took off my shirt and threw it into the room on the floor as the couple in the hallway watched us making out when Emanuel stopped kissing and told the couple, “Get a room of your own, Tony is my man to make love with not yours. No lady, I am not going to share my man with you, I know my man has a better in bed than yours and has a sexier body than the man you are standing with in the hallway.”
Emanuel lifted me into his arms and gave a deep and continuous kiss as he closed the door with his foot and carried me into the hotel room with our own privacy and laid me on the bed. Emanuel made out with me while helping me to undress until we were both naked when he began giving me a fully body massage. Emanuel started by massaging my arms from my hands inward, then my chest and stomach, and my legs from the ankles upward until he got to my cock. Emanuel sucked my cock until it was hard when he lubricated his asshole and my cock when he rubbed KY Jelly on his asshole and my cock. Emanuel sat on my cock to take it in his ass all the way to ride my cock while he moaned and held my chest playing with my nipples until I came deep inside his ass. After I came deep in his ass Emanuel asked, “How much did you enjoy getting your cock massaged deep inside my ass as I rode your cock until you came deep inside my ass Tony?”
I told Emanuel, “I truly enjoyed it Emanuel, my cock felt so good inside your ass as you rode my cock deep into your ass until I came inside you from all of the sexual excitement you helped create with us having sex as a gay couple after the man and women were watching us make out in the door way while you were holding and beginning to undress me while you were naked as they watched.”
Emanuel told me, “You are sexier than the man the woman was with who were watching us making love in the doorway like a couple of perverts. I saw the two of them making out in the hallway before you got here after I checked into the hotel room. The woman that was watching us making out was standing in the hallway without her shirt or bra on while the man she is with was sucking on her nipples as I was walking to our hotel room. Honestly, I would not care if the woman or the man she is with has a problem watching us as two gay men making out after seeing them making out in the hallway. It would not matter if they were to see us making love with each other as a couple of gay men, at least I ended up with a better and sexier man than she did.”
Emanuel gave me a deep enthusiastic kiss, and he rolled me over onto my stomach to massage my arms from the wrists inward, then massaging my back from my shoulders to my waist, then my legs from my ankles upward until he got to my ass. When Emanuel got to my ass, he massaged my butt cheeks while eating my asshole to soften it and prepare my ass to fuck. As my asshole became moist from the deep rimming he was doing with his tongue, Emanuel slowly worked his cock into my ass until it was all the way in. When Emanuel’s cock was fully inside my ass, he laid on top of me and held my hands with our fingers interlocked as he deep kissed me as my head was turned with his tongue. Emanuel slow fucked me for ten minutes as I softly moaned with gay sexual pleasure until he came deep inside of my ass. I enjoyed every minute of it, and I used my ass muscles to milk every drop of cum out of his cock while he was cumming deep inside my ass. Emanuel came deep inside my ass and kept his cock deep inside my and he asked me, “Did you enjoy the deep tissue massage of your ass with my cock in your ass Tony?”
I turned my head and said, “Emanuel, I loved every minute and every inch of it.” I wiggled my ass with his cock inside my ass and said, "I am ready for more if you want to fuck me again because my ass is yours to pillage. My ass is feeling good with your cock deep inside my ass.” I was enjoying every moment of gay sexual extasy being his bitch for him to fuck as much as he would like.
Emanuel kissed me and said, “Good I am going to fuck you again to give you another deep anal tissue massage Tony.” Emmanuel fucked me slow and deep as he held me close for ten minutes as I moaned softly with gay sexual pleasure before he came again deep inside my ass for my ass muscles to milk every drop of his cum from his cock as it was deep inside my ass for a second time. After he came, Emanuel kept his cock inside me as we kissed me as I my head turned facing him as he held me.
Emanuel rolled me over and we made out for another half an hour before I began feeling Emanuel’s cock getting hard again and got on top of him while he laid on his back. I slid his Emanuel’s cock deep into my wet cum filled ass and rode him like a cowboy in the saddle riding a horse as I rode his cock as we held each other’s hands as I grinded my ass on Emanuel’s pelvis while his cock was buried deep inside my ass. I moaned and told Emanuel, “I love being your gay little bottom bitch for you to fuck the shit out of my ass and fill my ass with cum. I am going to stay with you until check out time so we can stay naked in bed and fuck each other until morning when we get up, shower a and leave after you finish wearing my ass out Emanuel. I love you and I want you to keep fucking the shit out of my ass as your gay bottom slut.”
Emanuel gripped my hands tight as he looked into my eyes and screamed, “I am ready to cum slutty little gay bottom bitch. You are sounding like a little gay bottom whore as much as you want to be fucked in the ass after all the men you have already had fuck your slutty gay ass. I am cumming deep in your ass Tony, do you really want me to keep fucking your ass until we leave in the morning? I love having my cock inside your ass.”
I was so sexually excited that I joined Emanuel as we both gripped each other’s hands fit as my cock exploded hands free spewing cum all over Emanuel’s stomach and chest as I came on him while he was cumming deep inside my ass as my entire body tingled as I quivered and shook while Emanuels cock was deep inside my as I had a duel orgasm from my cock exploding with cum and an anal orgasm as his cock exploded deep inside my ass. With Emanuels cock inside my ass I looked into Emanuel’s eyes and told him, “Yes Emanuel, you can fuck me as often and as much as you want before we have to shower and check out of out hotel room in the morning so I am not smelling like cum when we leave so people are not looking at us as a couple of gay sex freaks even though we might be. I love being your slutty little gay bottom bitch so you can fuck the shit out of my skinny little ass all morning while you are wearing it out.”
Emanuel looked into my eyes and he told me, “Ok Tony. I will keep fucking you until we have to shower and leave at check out time in the morning so I can fuck the shit out of your ass as long as you let me get some rest between our fuck sessions, so I do not wear myself out. I am going to love having you as my slutty little gay bottom bitch until it is time for us to leave.”
I leaned down and kissed Emanuel before getting off his cock and laying down beside him as he held me in his arms as I faced away from him as he grinded his cock against my ass as we had our heads turned to continue kissing for a half an hour before Emanuel’s cock began getting hard again as he worked his cock back inside my ass and fucked my ass slow and deep. Emanuel reached in front of me and held my cock in his hand as we kissed and he continued fucking my ass slow and deep as my cock got hard in his hand. Emanuel started giving me a hand job by jacking me off as he kissed and slow fucked my ass deep until my cock exploded with cum all over the sheets of the bed as Emanuel was fucking my ass and kissing me until I was finished cumming. Emanuel rolled me onto my stomach and fucked me hard and deep as he held my hands tightly until he came deep inside my ass as I used my ass muscles to milk all of the cum out of his cock. After Emanuel finished cumming deep inside my ass he laid on my back and held me while he kept his cock inside my ass after cumming and we continued kissing as my head was turned on its side towards him until we both drifted off to sleep.
The following morning, I woke up to Emanuel fingerfucking me as he was sucking my cock after he had lubricated my ass to be fucked until I came in his mouth as he swallowed it before he rolled me onto my stomach and started grinding his cock on my ass until his cock was hard. Emanuel pulled my ass up so I was on all fours while I was on my knees, and he worked his cock deep into my ass and fucked me hard and deep in bed while he was on his knees. I was feeling so good that I moaned loud and told him loudly, “I love being your slutty little gay bottom bitch for you to fuck like the little gay whore I am. Keep your cock inside my ass and keep fucking me like the little gay whore I am. I can feel your cock is about to explode in my ass as much as it is throbbing deep inside my ass. Keep your cock inside my ass after you cum, I want you to fuck me like you are trying to get my faggot ass pregnant Emanuel. Keep fucking me and fuck my ass harder.”
Emanuel came deep inside my ass, and I leaned up to kiss Emanuel as he was cumming inside my ass as he held me while we were both on our knees as he kissed me until he finished cumming inside my ass. Emanuel and I got up and took a shower together to clean up after I began feeling the cum dripping on my leg from Emanuel's’ semen inside my ass. Emanuel and I made out in the shower kissing and holding each other as we washed each other off. We turned the shower off and got out to dry each other off with the hotel towels and got ourselves dressed in the clothes we had on the night before while smelling the heavy scent of gay cum all over the bed that made the hotel room smell like the room of a gay whore house from the strong smell of gay anal sex.
Emanuel and I gave each other a hug and a kiss before we held hands and left the hotel room together to check out while getting puzzled looks from hotel guests that may have heard us having gay sex with each other through the night and morning. Emanuel said our goodbyes while we held and kissed each other in the hotel parking lot, not caring who was watching before we got into our own cars and left for me to head back to the apartment I was sharing with Nessa and her daughters and that was the last time we ever saw or heard from each other again. It was a great gay sexual experience that helped make up for the past seven men I had gay sex with where the sex I had with them felt awkward to make me wonder if it was worth it. At least this time with Emanuel, it was.
