Caught in a Gay Personal and Sexual Relationship
After I turned thirty-three, I found myself reconsidering the direction of my personal and sexual relationships. My connection with my African American BBW partner, who was thirty-seven, continued to stagnate; we rarely had sex, and when we did, it was to satisfy her own desires during those brief moments when her daughters weren’t around. This lack of intimacy made me realize how much I missed having a genuine, fulfilling relationship with someone—one that offered both emotional and physical closeness.
Feeling increasingly dissatisfied at home, I started exploring the possibility of meeting men to pursue a lasting personal and sexual relationship, hoping to find the connection and permanence I craved. At the same time, I continued making efforts to meet women, particularly those who were beautiful African American BBWs regardless of age, as I was drawn to their confidence and allure. Through these experiences, I began to understand that my strongest sexual attraction was toward African American individuals, more so than Caucasian or Hispanic people. This realization guided my search for both meaningful companionship and intimacy, whether with a man or a woman.
After a string of disappointing attempts to find meaningful connection—both online and off—I decided to try something different. One night, feeling especially restless, I logged into a gay chat room, hoping to find someone who might understand the complexities of my situation. It didn’t take long before I started chatting with an African American man named Alan who was 43 years old. There was an immediate sense of ease in our conversation, the kind that felt rare and genuine.
As we talked, it became clear that both of us were navigating similar struggles. He shared how his relationship with his long-term Hispanic girlfriend that is a big and beautiful curvy woman with enormous tits and a thick and round ass like my African American girlfriend had grown distant, lacking the sexual intimacy and emotional closeness he craved. I found myself opening about my own frustrations, the stagnant connection with my partner and the emptiness that came from feeling more like a roommate than a lover. We bonded over the mutual dissatisfaction in our heterosexual relationships, realizing that neither of us felt truly seen or fulfilled personally or sexually.
The more we confided in each other, the more our conversations shifted from frustration to understanding. We talked about the loneliness that comes from hiding parts of ourselves and the yearning for a relationship where we could be wholly authentic. Our late-night chats became a safe space to process our feelings, share our hopes, and admit our fears. This mutual support laid the foundation for a deeper connection, as we both recognized the comfort in finding someone who understood our struggles from the inside.
Eventually, our conversations turned toward what we were truly seeking in future relationships. We were both honest about our attraction to men—specifically, to partners from diverse backgrounds. For him, the idea of a committed interracial relationship represented a chance to embrace his full identity without compromise. I admitted that my strongest attractions had always been toward African American men, drawn by their confidence and warmth. We discussed what it would mean to find a partner who not only shared our desires but also valued intimacy, trust, and long-term commitment.
Reflecting on these exchanges, I realized how transformative it was to share my true self with someone who understood. Our connection, though still new, gave me hope that genuine companionship and intimacy were within reach. Both of us left those conversations feeling less alone and more determined to continue our search, not just for fleeting encounters, but for relationships built on mutual respect, attraction, and the possibility of lasting love. These experiences became an important chapter in my ongoing journey toward authentic connection and self-acceptance.
After a few weeks of chatting with Alan online and in the man-for-man gay chat room, we both decided to exchange pictures. We started with ordinary photos—those candid moments captured by our friends or family—and gradually moved to nude pictures, showing both our front and backsides. There was a mutual appreciation for what we saw; we each found the other's photos attractive and reassuring, deepening our sense of connection.
After a few weeks of chatting with Alan online and the man for man gay chat room we both decided to send each other pictures of ourselves that were ordinary pictures that we're taking of us by our friends and family as well as nude pictures of ourselves showing our front sides and our backsides as we were naked both of us seemed to find the pictures that each of us sent to each other to be very attractive he understood that I was a white man with a tan completion, 6-feet tall weighing 165 pounds with a medium build having brown hair and hazel eyes with the sexy butt I'll let him know that my cock was 7 inches long, cut thick and I was into oral and anal sex with men both giving and receiving as a versatile top that loves to fuck and be fucked by the right man.
Alan told me that he was an African American male who had never been with men sexually before but was curious about exploring a relationship with an attractive gay or bisexual Caucasian male. He wanted to build a gay long-term personal and sexual connection, emphasizing intimacy and mutual attraction. Alan shared that he was a potentially gay African American male that is 5 foot ten inches tall, weighed 220 pounds, with short black hair and brown eyes, and has a 10-inch cock is cut and thick. He made it clear that he was not interested in being fucked by another man but had always been intrigued by the idea of fucking a beautiful Caucasian gay male in their sexy ass to see how much differently it feels fucking a man compared to having vaginal sex with a woman. Alan let me know that he wasn’t into having his cock sucked by a man, but he said he has always loved giving head to men that he had met at truck stops sucking a men’s cock in the bedroom cab of his semi-truck and swallowing their cum.
During one of our late-night chats, Alan mentioned the topic of our work schedules and how they might affect our chances of meeting in person. He explained that he is a full-time long-distance truck driver, which means he's often away for days at a time and does not have much free time. Alan asked me about my own career and when I might be available. I told him I am a full-time college student, so my hours are flexible, especially on weekends when I am most free. I was honest about being careful, since my girlfriend does not know about my bisexuality with preferences to have sexual relations with both men and women and because she does not know I am sexually attracted to men that I enjoy having sex with, I need to keep things sexually discreet. Alan wanted to know if I was comfortable with his complicated schedule, and I reassured him that we could make it work, meeting during daytime hours when privacy was possible, or at his apartment if that felt right. Our conversation made me feel hopeful that, despite the challenges, we could find ways to connect and spend time together.
When I asked Alan when the soonest date and time he would be available to meet with me so we could spend time getting to know each other and potentially make out and make love, I told him that after looking through his pictures, I found him to be very attractive and would love for us to get together as soon as possible. Alan replied that he would be leaving for a long-haul delivery drive tomorrow and would be gone for a week and a half. He mentioned that his girlfriend was working as a nurse at a local hospital, often gone for extended hours on 18-hour shifts, while my own girlfriend had just left for work a couple of hours ago without affection.
Alan offered to meet today, inviting me to his apartment—located at the same complex I used to live in, in building room 204 across from the swimming pool area. He suggested that I could take a shower and change clothes while he did the same, and that I could drive over, since it would only take about half an hour. I told him absolutely, that after showering and getting dressed, I should be able to arrive within an hour. As our conversation ended, we both expressed how we were looking forward to meeting, and Alan even admitted that he thought he was falling in love with me. The anticipation of finally connecting face to face filled me with excitement and hope for what might come next.
When I arrived at Alan’s apartment, I tapped the brass door knocker to let him know I was there. Moments later, Alan opened the door, greeted me with a warm kiss, and smiled as he complimented my casual look—shorts, T-shirt, and sandals. “You look really cute,” he said, his tone playful and genuine. I returned the compliment, telling him he looked incredibly attractive as well in his T-shirt and boxers, which made him grin even wider.
“So, what do you have in mind for us to do?” I asked, feeling the anticipation in the air. Alan leaned in, kissed me again, and suggested, “How about we sit on the couch and hold each other while we watch something on TV? There is not much on except soap operas, but that is fine with me if it is okay with you”. I hugged him and laughed, replying, “Soap operas are a lot of drama, but that’s okay for me—hopefully we don’t get involved in much drama ourselves.”
Curious about privacy, I asked if his girlfriend might be coming home soon. Alan reassured me, “No, she’s more than likely not going to be home until tomorrow unless there’s an emergency, which I doubt will happen.” With that, we headed to the living room, feeling relaxed and grateful for the quiet time together.
Alan held my hand as we walked together over to the couch and settled in to watch television. He turned on the soap opera, and as we leaned close, Alan wrapped his arm around me, gently rubbing my back and shoulder. The warmth of his touch felt comforting, and when I looked up, he leaned in and kissed me deeply, his tongue exploring mine in an enthusiastic embrace.
"I'm enjoying my time with you more than the soap opera," Alan whispered, smiling softly, "but I do enjoy the intimacy." I kissed him back and agreed, letting him know how I appreciated the closeness, then asked what else he had in mind. Alan kissed me again and suggested, "How would you feel about us going back to the master bedroom so we can lay in bed together and make out? Then we can see where things go from there." His suggestion excited me, and I told him it sounded enjoyable. Alan kissed me once more, then stood up, holding both my hands to help me off the couch. He lifted me into his arms, holding me close and passionately kissing me as I held his face deep tongue kissing Alan as he carried me into the bedroom.
When Alan carried me to the foot of the bed in the master bedroom he laid me into the bed, where I laid and watched him walk to the stereo in the bedroom to turn on soft romantic music that he slowly danced to as he undressed while tossing each piece of clothing he took off into the corner of the bedroom until he was completely naked. Alan came back to bed and crawled into bed next to me to kiss me while we were passionately making out as Alan slowly undressed me and tossed each piece of my clothing by the dresser next to the bed until I was completely naked in bed exchanging passionate deep romantic kisses as we held each other close. Alan began kissing and tonguing a path down my chest until he made it down to the head of my cock that he slowly kissed as he held my cock in his hand as he looked not my eyes and asked me, “Do you truly want us to be a gay couple in a committed gay relationship where neither of us sees and has sexual relations with other men so your beautiful cock and adorable ass will truly belong to me as we become gay boyfriends and eventually gay husbands when we decide to get our own place together and get married? Are you ok with being the woman in our gay relationship because I love sucking cock and swallowing cum, but I don’t get into guys sucking my cock and I want a sexy guy like you to be able to fuck while making love, but I’m not into men fucking me. I want a man to be the woman of the relationship and eventually replace my girlfriend. I know I will give you the best blowjobs you have ever received from men or women before and I will fuck you more passionately than I have fucked my sexy girlfriend. Are you ok with this?”
I suddenly became teary eyes when I gave Alan a deep and enthusiastic kiss and told him, “Absolutely Honey, I am fine with being the woman in our gay relationship. I am sure I will enjoy having you suck my cock if you stop sucking other men off at truck stops. If we are in a committed gay relationship with each other, my cock and my ass are yours. I will happily let you fuck my ass as your girlfriend and eventual wife; you will need to be careful when you are breaking my ass in though. I have never seen a cock as enormous as yours and the biggest cock I have ever had a man fuck me with was 8-inches cut and thick, and that hurt for a while at first, not 10 inches like you have that will definitely have my ass hurting when you start fucking me with your monstrous sized cock.
Alan said, “I understand and I will go easy on you while I am fucking you. My current and past girlfriends would not let me fuck them in the ass because of the size of my cock, so you will be the first man or woman I will have ever fucked in the ass. I will go easy on you and cherish the moment as my first time enjoying anal sex with anyone.” Alan leaned up and gave me a kiss, and he looked into my eyes and told me, “I love you girlfriend and I’m going to enjoy having your cock in my mouth and deep down my throat.”
Alan went down toward my cock and lifted my legs over his shoulders as he held both of my hands as he began deep throating my cock so hard and fast that I began clinching Alan’s hands with a tight grip as Alan made glugging noises as he sucked my cock all the way down to the base. Within minutes I was caught in a moment of sexual extasy as my cock exploded deep down Alan’s throat as I had the biggest sexual orgasm I had ever had with any man or woman before in my life. My cock exploded with the biggest amount of cum I ever felt pumping from my cock while my entire body was quivering and tingling with sexual pleasure to a point that I began getting teary eyes with the amount of sexual pleasure I was experiencing that was beyond any I had ever experienced with any other man or woman before. Alan was right, he gave me the best blowjob I had ever received before, and I loved every second of it.
After I finished cumming down Alan’s throat he rolled me over onto my stomach as he spread my legs and began eating my asshole to moisten it as he stuck his tongue deep into my ass when it was moist. Alan moved on top of me as he slowly worked his cock into my ass as I gripped the pillow tight from the high amount of pain I was feeling as Alan’s cock was stretching my ass more than it had even been before. The 20-inch double headed dildo that Greg used to fuck both of our asses at once years ago was not as thick and monstrous as Alan’s 10-inch cock. Alan eased his cock deep into my ass until it was all the way in as I strongly gripped both of his hands from the pain and pressure, I was feeling deeper in my ass that I had ever felt with any man before. Alan began to slow fuck me while his cock was buried deep in my ass as he kissed me with my head turned. As minutes went by my ass began to adapt and adjust to the feeling of Alan’s massive cock being deep in my ass to where the pain turned into sexual pleasure as my asshole was broken in to fit his cock. Eventually, the tightness of the grip I had on Alan’s hand subsided as our fingers interlocked and I began to moan with sexual pleasure as Alan and I continued to kiss.
Alan told me, “Your ass feels so good, I have never fucked any woman’s pussy that ever felt as good as my cock feels inside of your amazing ass.” Alan gave me a kiss and he told me, “Honey I’m getting ready to cum, do you want me to pull out or to cum inside your ass?”
I told Alan, “Your massive cock feels so good deep inside my ass. I want you to cum deep inside my ass. After you finish cumming I want you to keep your cock deep in my ass and hold me. As hard as it was for you to get your massive cock inside me and breaking my ass in for your cock, I deserve to enjoy the feeling of keeping it inside of me as you hold me and continue making out with me as your girlfriend.”
I could feel Alan’s cock explode deep inside my ass as I used my ass muscles to grip onto his cock to milk all his cum out of his cock until there was no cum left to milk. Alan held me and we continued to kiss as his cock stayed inside my ass for a half an hour when his girlfriend called and told him that she was going to be getting home from work early and letting him know she was going to be home in about an hour.
I went and took a quick shower as Alan stripped the cum soaked sheets off the bed and remade the bed with clean sheets and blankets. After I was finished taking a shower and Alan was done making the bed while putting the cum stained sheets and blankets into the washing machine, he came and gave me a kiss as I was drying myself off with a towel and he got in the shower to clean himself off as I was getting dressed in the clothes I wore coming over. After Alan took a quick shower, he came out and dried himself off with the same towel I used and threw it into the washing machine with the bedding he had already placed into it and quickly got dressed before giving me a kiss goodbye as he walked me to the door of his apartment. As I was about to leave Alan told me to be careful because I might walk by his girlfriend he lives with when I get to the parking lot outside of the apartment because she was on her way home from work.
I agreed with Alan that I would be careful not to give anything away about our gay sexual relationship if I passed her in the parking lot. To my amazement, I crossed paths with Alan’s girlfriend, Melissa, and I recognized her from when I lived at the apartment complex 5 years ago. I met Melissa at a Country Music Bar and she gave me a deep blowjob and we got naked and I fucked her and sucked on her massively large breasts with large nipples in the back seat of her car while we were parked in the empty Country Music Bar parking lot until I came deep inside her pussy while she screamed loudly with sexual pleasure and clutched my back with her finger nails while having a major orgasm. After having sex with Melissa she told me her boyfriend was out of town for his job, and she wanted to get laid since she rarely has sex with him when he is back in town for a few days every 2 weeks because her boyfriend doesn’t seem to have an interest in having sex with her for over a year when they last had sex before I fucked her in her car. Melissa had told me that she was beginning to wonder if her boyfriend was gay because he seems to be friendly with men while not seeming interested in sex with women when she tried watching a porn movie of women having sex with men with him and it did not seem to excite him sexually. Little did I know then her boyfriend was Alan who has turned out to be gay and wanted to have a gay sexually relationship with me without knowing I had fucked his girlfriend in the past.
When Melissa saw me in the apartment parking lot she looked like she was excited to see me when she came to me and gave me a hug and a kiss and she told me, “It’s been a long time since I last saw you when we met at the Country Music Bar and had amazing sex in the parking lot, we might have to do it again if I am ever lucky enough catch you at the bar again. You still look very sexy to me and the last time my boyfriend and I had sex with each other was more than 2 years ago. I still think he might be gay because when we did have sex it did not even feel like he really wanted to because he could not keep an erection when I was sucking his cock to try and get his cock hard enough to fuck me. The last time he fucked me was over 3 years ago when we were both drunk. Melissa asked me for my cell phone number, and she told me that we should talk and get together sometime. I know when we met before you weren’t having any luck getting laid by your girlfriend you were living with so you were having a lack of sex with your girlfriend like I was having with my boyfriend when we were able to get each other out of our sexual ruts with our sexual partners of the opposite sex at the time. If things have not changed with your girlfriend, we might have to do something about it again together sexually”.
I gave Melissa a kiss back and gave her my cell phone number that placed into her cell phone and she also programed her cell phone number into my cell phone and said, “Who knows, if you catch me at the Country Music Bar and you want to catch up, we can see where things go because things have not really improved sexually with my girlfriend I am still living with either.” I headed for my car to leave without drawing any further attention from Alan or his girlfriend Melissa. It felt strange knowing that neither of them has any awareness that I have had sex with both of them and I needed to keep it that way or I may end up losing the possibility of having either of them as a sexual partner to make up for the lack of a sex life that I had at home with my girlfriend.
A few weeks later Melissa began sending me text messages asking how I was doing while Alan was sending me emails while he was on the road as a truck driver. I advised both to keep the communications we were having with each other to themselves so it would not create problems in either relationship as a couple while letting them know that I was not going to share our communications with my girlfriend I was living with either.
After a month of Alan being on the road he sent me an email asking if I could let him know of a day in the coming week where I would be home alone so we could get together to make love to each other. And I sent an email response letting him know that I would be available for us to meet on Friday when my girlfriend and her daughters were going to be away until they get back from school sporting events at their school in the evening. Alan asked for me to come to the door naked wearing nothing but a robe when I come to meet him at the door and welcome him into my house to make sure no one else is home when he comes to my house to ensure our sexual privacy. I agreed to meet him at the door after I take a shower with nothing on under my green silk robe when I come to the door to let him in after he rings the doorbell.
On Friday afternoon Alan was at my front door and rang the doorbell and I answered the door and left him in the house before he reached behind to close and lock the front door after he was in the living room area. Alan held me and gave me a deep and enthusiastic kiss before looking into my eyes as he untied my silk robe and let it fall to the floor as he slid it off my shoulders after opening it to leave me standing in the living room fully naked. Alan held my ass in his hands as he continued to kiss me before asking where the master bedroom was and I held his hand and led him to the bedroom where I crawled into the bed and watched him as he turned on my bedroom stereo with soft romantic music in the background as he undressed and joined me in bed to make out as we were both fully naked. Alan started kissing his way down my chest as he held onto my cock and asked me, “Does your beautiful cock and adorable ass still belong to me?”
I looked down at Alan as he started kissing the head of my cock and told him, “Yes Honey, my cock and ass still belong to you to use any way you wish as we make love to each other. Do you still want to have a long-term gay sexual and personal relationship with me, where our bodies, hearts, and minds belong to each other and no one else?”
Alan told me, “You know it baby, I thought about you the entire time I was out on the road as a long-haul truck driver wishing you were sitting naked in the cab of the rig with me as I was driving. There were times I had to jack off while I was driving because thinking of our last time making love was making me so horny. I could not wait to be home to make love to you so much that I forgot to call my girlfriend to see how she was doing and I will have to figure out what to say when I get to our apartment. I am starting to think that maybe we might need to get an apartment of our own to share as gay lovers when I am back in town so we can spend our entire time together sexually.”
I told Alan, “I would love that, it would provide use with more privacy and personal time in our gay personal and sexual relationship to truly enjoy each other’s company to the fullest.”
Alan said, “Ok Honey, now it’s time for me to start working on this beautiful cock of mine that you are taking care of for me when I’m away.” Alan lifted my legs over his shoulders as he began sucking my cock deep and hard to it’s base and making glug sounds as he sucked my dick hard and fast as he held on to my hips until I had a massive orgasm feeling my whole-body trembling with sexual ecstasy as my cock exploded with cum deep in Alan’s throat as I screamed, “Oh my God”, while I was cumming.
Wen my cock was no longer cumming for Alan to continue swallowing my cum he rolled me over and started eating my asshole sticking his tongue deep until he felt my asshole was moist enough to slid his massive 10-inch cut and thick cock deep inside my ass, slow and easy until it was all the way inside to the base of his cock. Alan kissed me deeply as my head was turned as he held my hands above my head and began fucking my ass deep and hard as I moaned with sexual pleasure until Alan’s cock exploded deep inside my ass as I used my ass muscles to milk all of the cum out of his cock. After Alan finished cumming deep in my ass he held me as he kept his cock deep in my ass for 10 minutes as we continued making out until Alan said he had to take a quick shower and get dressed to head home to his apartment with his girlfriend.
While Alan was taking a shower I changed the cum stained bedding and placed them into the washing machine to wash before going into the shower to join Alan in cleaning off where we made out for a few minutes before drying ourselves off with a shared towel before we both got dressed and I walked him to the front door where we kissed and said our goodbyes as Alan left for his apartment.
A month later Alan sent me an email asking if I had another Friday available for us to get together for a quickie when he gets home. When I said I was available he told me to greet him at the door wearing the same silk robe with nothing else on so we could make love when he gets to my place.
When Friday afternoon rolled around I was sitting and waiting naked in my silk robe when Alan came to the door and quickly lifted me into his arms and carried me to the master bedroom where he set me onto my feet on the floor as he took off my silk robe and quickly undressed as we both got into bed naked and made out as Alan went straight to my cock and lifted my legs over his shoulders and began sucking my cock hard and deep until my cock quickly exploded into his throat as he swallowed my cum. After I was no longer cumming Alan quickly got up and put his clothes on and he went to the bathroom to rinse his mouth before coming back to the bed, where I was laying naked, and gave me a kiss and said, “I’m sorry, I really have to go and get back to my apartment that I’m still sharing with my girlfriend, goodbye, I’ll catch you later next time I’m in town.
Two months later Alan did the same thing to come to my house and give me a quick blowjob and leave. It became a pattern where every 2 months Alan would call and do the same thing to stop by and give me a quick blowjob and leave for the next 10 months. It was a pattern that was beginning to make me become a little suspicious that something was going on with Alan to where he might not be acting faithfully with me or his girlfriend Melissa.
Alan’ s girlfriend Melissa was calling me to complain about Alan not being around to have sex anymore when he was home from driving as a long-haul truck driver until one night when Melissa called me crying and asked me to meet her at her apartment at the apartment complex I used to live at. When I arrived at her apartment Melissa was naked when she greeted me at her apartment door and she gave me a kiss and a hug as she led me to the couch, where she sat next to me and held me. With Melissa being naked and intimate with me I was not sure what to expect.
Melissa told me, “Alan had moved out and got a one-bedroom apartment with a guy he had met at a truck stop that Alan admitted he had been seeing for the past 10 months who has been riding with him on long hauls on the road with him. Alan told me about it after I got home from work and saw that he had moved all of his things out of the apartment and called him to ask him what was going on and he broke up with me. Alan told me that he has been seeing and having sex with you as well for the past year and I figured I could see if that as true or not by having you come to my apartment without giving you directions since I have never had you over to meet me at my apartment before. Seeing that you knew exactly where the apartment was I was able to see Alan was being honest with me when he told me you were having sex with him since the day I saw you in the apartment parking lot for this apartment building Alan and I have been living at for the past 7 years. According to Alan, he was fucking both of us because he said that he was fucking you in the ass and you loved having his massive cock deep inside your ass when I would not let Alan fuck me in my ass. Alan claimed that was the reason he turned gay was because I would not let him fuck me in the ass when he wanted to. I guess in the end we were both his bitches to fuck at will if he wanted to. I suspected Alan was gay and was cheating on me with somebody else, but after we had sex with each other in the past, I did not think it was going to be you he was cheating on me with. Now you can see me naked, knowing we had sex with each other before. I do not have a problem with you being gay or bisexual considering the lack of sex you are having problems with your current girlfriend on. The reason I am sitting her naked is to let you see who you just fucked for a second time when you secretly cheated with my former boyfriend. Thanks to Alan, I know you are just a bitch to be fucked like me so you can just fuck me for real and go or just go and I lever want to ever see you again after this.”
I got up and left Melissa’s apartment and never saw her again while feeling embarrassed for Melissa finding out I was being fucked by her boyfriend as his temporary gay lover since it turned out that Alan was cheating on us both and screwed us both in the end.
