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 decided to fly 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.
Her 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 while 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 as 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. However, 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 BBW who was beginning to make me feel like I was being sexually deprived from what had almost 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 again. 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, the first six guys I met in the gay chats that were awkward sexually awkward because I did not know what I was getting into strand sexual moments. Two of the men I went to meet at their homes and two of the men came to visit me at my apartment.
One of the men I met at their home that didn’t work out was Nathanial of whom was 5-foot and 8-inches tall bisexual white man that had brown hair and brown eyes, weighed 165 pounds drunk and naked when he met me at the door of his trailer home who gave me a kiss when I met him at the door 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 briefly made out kissing each other before he turned over on his side with his back and ass facing toward me as he grinded his ass against my cock as I held his cock in my hand and kissed on his ear and he passed out as we laid in bed and started snoring as I held him naked. After holding him for ten minutes with him snoring I just got up to put my clothes on and left.
The second one that I met with a guy at his home that did not work out sexually was Michael. I met Michael at his home in a trailer park, and he was living with a roommate that was a 60-year-old Crossdresser that was not attractive. 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 was wearing makeup and a robe as he sat in the living room watching gay sex porn on the television as Michael and I said hello to him as we passed him while we went back to Michael's bedroom. Michael and I made out and kissed as we undressed each other and crawled into bed to continue making love to each other while we were making out in his bed. Michael and I switched side 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 came into the bedroom with a beer and sat down in a chair by the bed to watch us sucking each other’s cocks. I stopped sucking Michael's cock as Michael continued sucking my cock and I asked his cross-dressing roommate, “What are you doing in the bedroom, I can’t remember Michael or I invite you into the room to join or observe us having gay sex with each other.” Michael cross-dressing roommate responded saying, “I did not need to sit in the living room to watch gay porn when I am able to come in my 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 one is able to sit back and watch them having sex with other men.
As I watched the crossdresser masturbating while I began eating at Michael’s asshole to get his ass moist, so it was ready for me to fuck. When I was able to finger Michael's asshole with comfort, I rolled Michael over and slid my cock into his ass while he was laying on his stomach and I fucked his ass deep as we held hands with our fingers interlocked as I kissed him while his head was turned towards me and Michael's crossdressing roommate took his clothes off as Michael and I were making love. The crossdressing roommate sat on the bed and started fondling my ass as I was fucking Michael deep in his guts when the crossdresser said I need to get some of this 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 the crossdresser’s cock was hard, he said, “Since you are fucking my boyfriend and roommate it is my turn to fuck you. Your ass is as beautiful as my boyfriends, and I want to take my part of it since you are fucking my personal gay lover.” The Crossdresser 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 deeply and slowly as Michael and my hand and fingers interlocked as we continued kissing. The feeling of the crossdresser’s cock deep in my guts slow fucking me while kissing my neck made my cock explode deep inside Michael's ass and making him moan as he was feeling me cum filling his ass and Michael began moaning loudly as the crossdresser started fucking my ass hard and deep after I came deep in Michael's ass. Even though I had already cum inside Michael's ass he told me, “Keep your cock inside my ass, this feels so good having your cock deep inside my ass while my roommate is fucking your ass deep and hard and it’s making me start to cum on the bed below me and I’m loving this.” Shortly afterwards I could feel the crossdresser cum deep inside my ass as he moaned with sexual pleasure holding us both tight until he was finished cumming deep inside my ass when the crossdresser got up and sat in the chair by the bed and said to me, “Okay, I’m finished now, so you can go home.” When I looked at him and said, “Are you serious.” Michael looked at me and said, “Unfortunately, yes, he is. My boyfriend and I have been a couple for 5 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 is fucking them while their cock is still deep inside of me. It made it feel like my boyfriend was fucking my while he was fucking you while my ass filled with your cum.
After that I felt like suck a cheap and easy anal whore after I put on my clothes and left to go home and I could feel my underwear getting wet as the cums was dripping out of my ass as I drove.
The first of the men that came and met me at my apartment and have sex with me was Jonathan, who came over and made out with me as we took each other’s clothes off and we took a shower together. After we washed each other off Jonathan gave me a deep blowjob while we were in the shower, I came in his throat, and he swallowed it and gave me a kiss as he dried himself with a towel and got dressed and let the apartment without me ever seeing or hearing from him again afterwards. It made it feel like the only reason he came and gave me a blowjob was to get a shower and the blowjob was nothing more than an exchange for a shower.
The 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 who 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 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 of 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 him as he moaned with joy and pleasure until I finished cumming deep inside his ass. After I came deep inside him Juan gave me a kiss and we washed off Juan turned off the shower, and he held me and gave me a deep and passionate kiss as he took hold of my cock and stroked it as we kissed until it was hard when he got down and kissed the head of my cock and stood back up holding me and my cock close and gave me a deep passionate kiss before he looked into my eyes with a horny and passionate look as he said, “Ok Honey, I’m ready for you to go with me in your bed and fuck the shit out of my ass while I’m on my stomach and cum deep in my ass with your cock staying deep inside my man pussy until your finished cumming, then I want you to roll me over onto my back and fuck me the same way. I can feel your cum still inside my ass after you fucked my ass in the shower and 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 Honey.”
I went to bed with Juan and when he laid on his stomach, I stuck my cock deep into his ass that 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. When I told him I was 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 and do not pull your cock out to roll me over until you finish cumming in my ass Honey. I am loving it.” I followed Juan’s request and stayed inside his ass for five minutes after I finished cumming as we kissed and 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 as I leaned forward holding his shoulders and looked into my face and said with a demanding look on his face, “I want you to fuck me so hard that I will be walking with a wobble for days with me dripping your cum all day when you are done fucking my ass. I love your cock deep in my ass more than my boyfriends. Your cock feels so good in my man pussy.” Suddenly 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 what he meant by, “Why did you say my cock feels better in your ass than your boyfriends?” 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, “Shouldn’t you take a shower and clean yourself off before you leave?” 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 full of your cum, I really enjoyed I making love with you as wonderful as your cock felt inside my ass. When I brought up my boyfriend it was because I decided to cheat on him by letting you fuck me after I caught him fucking another man in our bed as I watched them fucking while I stood quietly in the hallway watching without my boyfriend ever 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 guy in our bed. When my boyfriend finds my underwear filled with your cum stains from your cum dripping out of my ass I am going to let him know that I did fuck another man after I saw him fucking another man in our bed and tell him that if I ever catch him cheating on me again I will leave him and find another guy to fuck me permanently as their gay boyfriend and lover instead of his.” I never heard from or saw of saw Juan again after that and it felt a little 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.
Dan was the sixth gay man to hook up with me sexually and the third guy I met for sex at my apartment and having 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 six inches long, cut, and thick. Dan did have a nice ass, and he only liked having men fuck him in his ass and only fucked women’s pussy when having sex with them and that was it. When Dan came over to my apartment he didn’t 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 pull up his pants and left when I finished fucking him. As boring as our gay sexual encounter was, we never got together sexually again.
A month later I met Greg on the gay chat room, and he became the seventh man I met with for a gay sexual encounter and the fourth guy I had sex with at my apartment, and he said he was into kinky gay sex. Greg told me he loved giving men blowjobs and prostate massages to give men an explosive orgasm from the blowjobs he gives. When I asked Greg what his physical stats were, he told me he was a bald gay white man with brown eyes who was 6-feet tall and 175 pounds with an 8-inch cock and was versatile sexually with men.
When Greg came to my apartment, he came in with a small duffle bag. When I asked Greg what was in the bag he 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.
When Greg and I were in the bedroom he asked me, “Can you please take off all your clothes, and to lay comfortably on your back.” When I did so Greg told me, “You look very sexy, I can’t 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 finger you while I am giving you a blowjob?” I told Greg, “I am ok, you can do whatever you want with my ass and my cock while we are having sex together Honey.” 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 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.”
I told Greg he could go ahead 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 and get up onto your knees while the dildo is still in your ass so I can put the other end of it inside my own ass so we can fuck each other with the double ended dildo to give each other anal sexual pleasure at the same time.” When I got onto my hands and knees Greg got onto his knees behind me facing the other way and put the other end up the 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 both moaned with sexual pleasure until we came onto the bed sheets.
After we 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.” 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 to 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.”
As weird as it left me feeling in the awkward way we had man on man gay sex together, we never got together to have sex again afterward.
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. Emanuel was the first Hispanic guy that I ever had who made love to me with romantic man on man gay sex as the first Hispanic man that ever 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 and a 7-inch cut and thick cock that was just as he had described to me when I asked him in the man for man gay chat about his physical stats.
When Emanuel made a room reservation for us he told me that he was going to give me a full body massage that I would never forget and he left me feeling excited when I was left thinking about it all week after he originally discussed his sexual ideas he wanted to share about what he wanted to do with me sexually when we were able to get together. On a Friday night as we were chatting in the man for man gay chat he left to go and check in to our hotel room and got back onto the gay chat to let me know he checked in to the room after he got there and checked into the room. After Emanuel provided me with the name of the hotel and the address and room number I took a shower and got dressed in shorts, a t-shirt, and sandals and 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 already fully naked. When Emanuel opened the door, he 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 5 minutes with the man and woman looking 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 remained in the hallway watching us making out when Emanuel stopped kissing and told the couple, “Get a room of your own, this man is mine 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 and more sexy 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 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 before he sat on my cock to take it in his ass all the way to ride while he moaned and held my chest playing with my nipples until I came deep inside him. 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?”
I told Emanuel, “I truly enjoyed it Hone, my cock felt so good inside your ass as you rode my cock deep into your ass until I came inside your 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 meme while you were naked as they watched.”
Emanuel told me, “You are sexier than the guy that woman was with who were watching us making love in the doorway like a couple of perverts when I saw the two of them making out in the hallway. 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 guy, she is with was sucking on her nipples as I was walking to our hotel room. So honestly, I would not care if she or the guy she is with has a problem watching two guys making out after seeing them making out in the hallway. For me, it would not matter if they were to see us making love with each other, at least I ended up with a better and more sexy 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 while slow fucking me for nearly 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 of my ass. After Emanuel came deep inside of me and still had his cock inside of my ass he asked me, “Did you enjoy the deep tissue massage of your guts with my cock in your ass Honey?”
I turned my head and said, “Honey, I loved every minute and every inch of it.” I then wiggled my ass with his cock inside of me and said, "I am ready for more if you want to fuck me again because my ass is yours to pillage." My ass was really feeling good with his cock deep inside of me and I was enjoying every moment of 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 Honey.” Emmanuel fucked me slow and deep as he held me close for 10 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 with my head turned for as he held me until he rolled me over and we made out for another half an hour before we both 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.
After I finished taking a shower, I put my clothes on, and Emanuel and I gave each other a hug and a kiss before I left the hotel room 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 sex with that the sex I had with them felt so awkward to make me wonder if it was worth it. At least this time with Emanuel, it was.
