So after a few years break from being on here I have decided I missed you SG ladies. I have also decided to make a valid attempt at posting more on here even tho I don't think many will really care or that I will have many people that will be at the edge of their seats to see what I post next lol.
So I figure this would be as good as any post to start with a lil bit more about me. I recently turned 40 and am single, never married, and no kids. As my username says yes I am a bi dude but it is more with regards to cuckolding. I grew up in a small conservative town so as a young man leaving to college I was very much the closed minded, ultra conservative, uber religious guy. I was very anti homosexuality, anti interracial relationships sort of guy too. I dated around a lil but it wasn't til the first major relationship in college that really turned my life around.
Revised version of this: 4/3/22
The start of my freshman year of college and the wicked twist and turns it took would forever change my outlook on the world, myself, dating, and everything I held myself to as a young adult. I grew up in a small conservative town so as a young man leaving to college, I was very much the closed minded, ultra conservative, super religious guy. I was very anti homosexuality, anti-interracial relationships sort of guy too. I dated around a lil but it wasn't until the first major relationship in college that really turned my life around.
It started out as a normal relationship but soon became the catalyst to a whole new world and lifestyle. Jessica was a sophomore and we hit it off almost instantly midway thru Fall Semester. She was a relatively short girl. We were both about the same height. She was thin but curvy in just the most perfect way with pronounced sexy/cute booty and medium sized breasts with wavy curly brown hair. She exuded both an innocent look yet very sexy look all rolled in together. Jessica and I had been dating for about a month and a half when I got what was a heart dropping call from her one cold December evening.
She said in a very loving yet sorrowful tone “We need to Talk”.
The words anyone hates to hear and dreads what is to come next. She went on further to say can we go out tomorrow for dinner as usual and we can talk. She didn’t want to do it over the phone. Oh great, I thought now to wait in suspense to be broken up with and for what, why, what could have happened? My thoughts raced all night long wondering what could have happened. Things were going so great.
Needless to say, I did not get much sleep the previous night and woke up just as distraught as I had gone to sleep feeling. The day dragged and dragged. Fridays for Jessica and I were busy days as we both had classes and other obligations that kept us from really seeing one another very much on Fridays until early midafternoon. I walk out of the campus center and there she is walking up flashing a smile as she flipped hair and head around and there those blue eyes of hers. She runs up as she catches me in site and gives me a big hug and kiss. Not at all what I was expecting after last night’s call.
She releases and looks back asking "What’s wrong baby? Please relax she says dinner tonight at 6 okay. I have to go, see you later tonight. LOVE YOU!" she yelled as she sauntered off with 2 of her friends.
So 5:45pm rolls around and I walk up to Jessica’s dormitory and walk in and up to her hall. I was a regular presence so I could come and go with respect to what time it was and make my way up to Jessica’s hallway. The suspense was nearly too much as I walked to her dorm room door. I knock and hear Jessica say “Just a second, I'm almost ready”. The door swings open and out pops Jessica looking ever so adorable in some thick winter vest thing and tight long sleeve shirt under with some very form fitting jeans and calf high boots. As we headed off to go to dinner it was as if all was normal nothing out of the usual.
Midway through dinner she says “Okay, so you know I absolutely love and adore you, right?"
"Yes." I say in a somewhat guarded and drawn-out tone.
This is where she expressed some potential issues in the relationship. Now Jessica was a couple years older so one could say she was more experienced and had been around the block more than I had at that time. She was not mean or rude about but was very frank about one simple underlying fact. Even though I was a "grower" I lacked the adequately sized tools to properly do the job she exclaims. As nicely as she could she expressed that when not aroused it was laughably tiny hands down the smallest, she'd ever seen and that even though when aroused I was okay it was just not enough. I unfortunately do have an extremely tiny penis when not aroused it is regularly about 0.5” to 1.5” at best and aroused between 2.75” to 3.25”. She needed more and looking back now I couldn’t really blame her.
Talk about a blow to a guy’s ego and self-esteem. This is where I learn Jessica was very much a size queen. The bigger the better. So as gently as she could, she explained and informed me of what she proposed and some of her history with guys with much larger cocks and the sizes.
Jessica was very certain and clear in the fact that she loved me and that I was the best boyfriend she has had but that she needed more in bed. She then goes on to explain that her best friend Brandy suggested ethical non monogamy. I sat up almost immediately with what revelation. Jessica obviously noticed the anger in my face.
“You told brandy all of this? She knows about my….”
Jessica interrupts me mid-sentence, “Please don’t be angry and, don’t worry she knows everything about me and is my best friend she would never say anything”.
She then goes on to say “See you aren’t even mad or angry about the suggestion of ethical non monogamy”. She was right I totally missed that.
So, I ask her “What in the hell is that?”.
Jessica continued on that she truly did love me and that as a guy my personality my caring nature everything about who I was as a person was everything a girl could want or ask for just that one thing.
So, after some thought and consideration I told Jessica I was not sure about all this. Jessica had explained that we would still be intimate but that when she needed, she would have intimate lovers that fulfilled the need she desired and could not have and that she would always keep me informed and never lie about anything that happens. With my upbringing this was way off the map from what was right and from what I was initially comfortable with. We went on Christmas break and Jessica and I had agreed before actually moving forward that she would give me time over the Holidays to think more so on it and make a final decision. This Christmas break felt like an eternity for me. The constant thought of that conversation clouded my head the entire holiday. So many mixed emotions of fear, uncertainty, insecurity, and doubt. A lot of things I was not accustomed to feeling. What I was dealing with was definitely not conversation to be had at all I was stuck in a whirlwind of torment and torture as what to do.
We came back from the holidays and Jessica and I met up together and greeted one another as usual. Jessica looked at me with a look of desperation eagerly wanting to know what I had decided.
I told her “Okay…. I will give it a shot but I can’t promise you that I can do this.”
I thought, worst that could happen is that doesn't work and we break up. I struggled greatly the first couple weeks. Nothing really happened until a Wednesday rolled around. This was usually a night out, her with the girls and me with the guys. I went with my buddies to the next town over to barhop and she went out with Brandy and Melissa.
I get a call from Jessica saying tonight is the night. My heart sank I had hoped that maybe it was just a dream and this would not actually happen. The reality of it all finally sank in. Talk about a real mood changer. The only thing I could think to do was say ok babe have fun and talk to you tomorrow.
Jessica was rather considerate and intelligent and eased me into it all and didn't just open up full throttle the next day. She had a key to my room and could easily sneak on in. I didn’t have a roommate so it made for some great nights when she would surprise me. I had made it back to my room around 2am and immediately crashed on my bed. Thursdays were typically a slow and easy day for me. So, shortly after crashing on my bed at around 4am Jessica sneaks in and slips in to bed with me.
I woke up the that morning around 8am smelling her hair in my face and thinking wow she’s here maybe last night wasn’t the night. I squeezed, hugged and kissed the back of her neck. She rolled over barely able to open her eyes and when she does, she looks at me and says “Oh my God last night was great baby. Thank you for allowing this”
BAM!! If I wasn’t already completely awake before I was now. She went on to tell me she had ran in to a guy she knew from high school and had always kind of had a thing for. She continued on with her account from the night saying they were drinking and laughing and having a great time catching up and then he kissed her and that was it. That is when she went for it.
I asked her “So… the issue is size? How did you know or how will you know if the guy has the size?”
Jessica responded saying "It was a well-known thing back in high school he was packing."
I continued, "How about others?"
She said “Well I will just check when I am dancing with them and rubbing my ass up on them before I decide”.
So many more questions raced but Jessica just leaned in and kissed me and said “Can we just cuddle and talk about this later babe I just wanna enjoy this time with you right now”.
I could not deny her request I mean it felt so good to lay there with her in my arms knowing that whatever did happen last night she still came back here to me and wanted to be with me. We talked later that day more about the night where she spilled all the details about the night. I was flooded with a mix of emotions jealousy and excitement. Yes, excitement.
The more she told me the more aroused I became at hearing it all. I could not understand it all. How could I feel everything I was feeling? It went without notice of Jessica’s eyes.
She questioned me “Babe? Are you? OMG!? Yes, you are! Babe you are getting all hard! OMG this is great!”
I couldn’t lie or hide it. I mean I was sitting there in boxers and athletic shorts. Jessica said “OMG Brandy said that for sure this would happen. I can’t believe it!” she shouted.
I immediately rushed to her and said "Shh not so damn loud."
Things really began to change at this point. Jessica and I immediately wasted no time with regards to my excited state. I would say was the best sex we had, had together. The amount of passion was undeniable. Well at least I thought so. I mean it was great but it was obvious now how Jessica did need more I could totally see it now. I could now see beyond my own view and feelings afterwards. There was definitely a lot more happening in our relationship than I could even have imagined.
We talked afterwards and I said “We need some rules for this all."
Jessica with a questioning look said “Rules?”
I responded “Yes, rules. No guys we both know or that go to school here with us. I don’t need the bs gossip. Brandy knows but no one else. Finally, just be careful.”
Jessica smiled a great big smile and said “I can totally agree and accept all of that babe”. Just like that it was like I completely gave in to it all as if it I had not even had a single issue with any of it. Jessica then asked if on Saturday night I would go out with her and Brandy and watch her find a new guy. As if there was really an actual choice in the matter. Jessica could that I was in and immediately just said come pick us up around 8 O’clock baby.
Saturday came and as requested I showed up to pick Jessica and Brandy. Once I got to Jessica’s door I knocked and when Brandy opened the door there was Jessica. I was awe struck at what she was wearing. She stood there in these crazy high heels, super tight almost see thru black dress that accented every curve of her body in just the most perfect way. It was a mix of sexy and slutty all at the same time. Brandy awoke me from the trance I was in looking at Jessica with a clearing of her throat and a hard "HELLO!".
I stammered in my response “Uh uh sorry. Hey there, wow you 2 look absolutely amazing!”
Brandy with an evil and devilish look within her smile laughingly said “Yeah, I told her if we are going out to get you some real cock then we need to look extra HAWT! Speaking of cock, I told Jessica I just had to see how bad and tiny yours really is and she said it was ok. So, let’s see it! Like right now!”
I looked at Jessica hoping this was a joke and she just shrugged her shoulders and said “Do it baby.”
I stepped in and the door shut behind me and Brandy taking a chair and setting it in front of me to sit down at eye level with my crotch. I started to undo my belt and Brandy was getting annoyed with how slowly I was going and sits up and says “Listen just take them off or I will do it for you” before sitting back in the chair again.
I begrudgingly hurry to it and just drop my pants and then my boxers immediately after. Brandy blurted out a spontaneous obnoxious "HA!" And immediately slapping her hands over her mouth as she could not contain her laughter. As I hung my head in shame Jessica almost immediately coming to my defense rushed around in front of me standing between Brandy and I, angrily saying to Brandy “You promised not to be mean or rude!! He is my boyfriend and I love him. Don’t you dare!”
Brandy immediately sat up in seriousness and said “I am so so sorry I just wasn’t actually expecting that please I am sorry.”
Jessica said “Ok but you just can’t be like that and hurt him. It does grow, it doesn’t just stay that small.” Jessica turned around and began to kiss my neck and run her fingertips up my inner thigh up to my crotch and back down. She certainly knew how to get me going. Jessica turned away for Brandy to see and said “You see what I mean?”
Brandy with a somewhat shocked and confused look on her face said “Wow ok yeah that is kind of impressive that from that small it gets to that. I mean it is still small but still wow I didn’t expect that.”
I looked at them both and said “Ok are we done now? Is my duty as amusement for the beginning of the night over?”
Jessica simply nodded and said "Yes baby, I am sorry please pull your pants back up."
Once we arrived at the club that the girls loved going to things really just started out like another night out for us. Then as we sat at the bar for a moment both girls perked up and seemed to get all excited. I could tell they had spotted and seen something or someone they liked.
They whispered to one another and then Jessica looked at me and said “Babe stay here and just make sure no one slips anything into our drinks over there ok.”
I turned and watched as they walked away towards this group of guys that had just walked in. I sat there watching and my mind racing with thoughts of am I really doing this? Am I really watching my girlfriend pick up some guy? I don’t know why I bothered questioning myself I knew that yes, I was and it was exciting me. The plan was primarily for Jessica to find herself a guy to leave with and hopefully Brandy as well. As the night went on, I could see them both really enjoying the guys they had targeted and saw Jess working her magic and hips. She initially had started flirting with one but looked as though she had shifted from him to this other guy and I could only guess that she felt the first was packing enough of what she wanted. Brandy didn’t seem to be having the same luck as Jess. Not that Brandy wasn’t attractive or anything she didn’t have remotely the charismatic personality that Jess has. As the night winded down I could see Jess being led out of the club by the second guy and Brandy walked over to me and grabbed me telling me we needed to go now. So, I followed and we got into my car and followed behind Jess and her guy of choice.
Brandy said “So, Jess told him that you and I would come pick her up in a lil while once we know where they’re going.”
I looked back at Brandy with a questioning look.
Brandy said “Yes, she told the guy she has a bf and that you and I would pick her up after.”
I responded “And he had no problem with that or anything???”
“Obviously!” she answered in an annoyed tone.
Once we knew where they had gone Brandy and I went to this 24-hour diner 5 minutes away. It was around 2:30am when we got the call to come and get Jess. As I pulled up, she came walking out and passed out in the back seat almost instantly. When we got back to Jess’ place Brandy got out and suggested I just take Jess back to my place. We got back to my place I woke Jessica up and she only asked for us to go right to bed and just talk in the morning.
I woke up the next morning before Jess as she was rather exhausted. I was making breakfast as she snuck up from behind me rubbing on my crotch and says “Good morning to the best boyfriend ever.”
I turned, we hugged and kissed and I said “Anything for you babe.”
As we sat eating breakfast, she began to explain the night. So when the group of guys walked in there was one guy she thought was HAWT. He could have been Brad Pitt’s brother she went to say. I didn’t really focus on them that much obviously. She went on to say that as they talked and she danced a lil he just was it and wasn’t what she was looking for and that his other friend the one she left with was far more of an aggressive alpha male dominant type and it got her all excited. So that’s where the shift happened and she made her move over to the other guy. She could tell he was packing too cause of the bulge in his pants and when she was dancing with him she could feel just how huge and thick he was as she rubbed her ass on his crotch.
I then asked “Well what happened with Brandy? Why didn’t she leave with anyone?”
Jess said “Let’s just say... she well... she just kind of did a Brandy thing, and kind of turned the boys off”
At the point I didn’t ask any further as I knew she would not say anything more as to what Brandy did or said. Jess went on to say that she told the guy she wanted to get out of there but that her bestie and her boyfriend would need to see where they were going to pick her up later at.
I piped up asking “Well what did he say to that?”
She went on to say that he was initially taken back but said “So your boyfriend knows you are here and we are gonna leave and fuck?” To which she nodded and gestured over to me. That’s when he took her by the hand and led her out the door. Jess went on to say how that’s when things got real serious. Once they got in his car, she went to explain how he undid his pants right then and his monster 9” cock flopped out.
Her jaw dropped and he said “Well….? This is what you are here for so get to work.”
She couldn’t help herself his forceful and aggressiveness and just the beauty of his cock she was entranced and went straight sucking on it like her life depended on it, she went on to explain. “I could barely get my mouth around it, it was so thick. But I did and took every inch down. I felt so slutty but I loved every bit of it baby. I sucked and sucked and then he shoved my head down as he came and Oh My God, he shot the biggest load ever! I couldn’t swallow it all, it like drooled out and down the shaft of his cock. When he let me up, he told me not to forget to lick up the rest that I knew I didn’t want to waste a drop. So, I did as he told me and left nothing behind. Then we go to where we were going and before the door closed, he pulled up my dress and ripped my panties off, spun me around and pushed me against the door and told me he was gonna fuck me hard like the dirty cheating slut I am. I was worried cause of how thick he was but OMG! As soon as he slid it in, I was in absolute heaven. He filled every inch of me babe. All I could do was moan and tell him that yes! I was a dirty cheating slut that loves big cocks. I felt bad initially not making him put a condom on but not like I could have anyone he was too in control. Thank God for Birth Control right babe?” I replied I uh guess so. She continued “He was merciless, I mean he practically bruised my uterus with each thrust. I came twice before he unloaded in me. Once he shot his load, he slapped my ass and simply told me nice fuck maybe we can do this again sometime and that he was going to bed. That’s when I called you guys to pick me up. I felt so slutty as I pulled my dress back down and could feel his cum dribbling down my leg as I walked out to the car. I am still sore right now but damn that was great babe. I can’t thank you enough for all of this, your really are the best boyfriend ever!”
As the weeks went on things seemed to progress with Jessica and her exploits. She didn’t seem to keep it to just James and the guy from the club she had met another 2 different guys. Jessica had expressed not wanting to get too attached to James or any guy because she didn’t want to mix feelings and emotions into it. So, it was weeks and weeks and 2 or 3 guys more before it ever manifested to my watching and or joining in on the action. I don’t know if my watching and joining was Jessica’s idea or another of Brandy’s that she dropped in on Jess.
Watching for the first time was extremely difficult cause I got to see what she looked like really enjoying sex and getting off. Something I had thought I had seen with us until I saw it for real. That is when I really began to understand the difference and actually enjoy seeing her get off and get what she needed and wanted that I couldn’t give her.
Once I began to watch and then eventually join in that is when things really escalated quickly. It took several times of watching and joining before things really went beyond what my mind could expect. Primarily any joining in that I did was mainly fourplay with Jessica as it was more sensual and love making than the rest of the action happening and also Jessica loved me eating her out after her lovers had finished sex with her and a few times no condoms so there was plenty of her lovers’ cum left inside of her. Then, what to me at the time was the worst thing that could happen, did of course happen. Jessica and her extremely well-endowed lover were about to be in the thralls of passion I was kissing her deeply and kissing her neck and breasts and she pushed my head lower and lower to my initial thought was to please her orally and get her going as we had done before as she love my oral skills. However, this time as I was about to begin, she sat up and pushed my head forward away from her and she guided her larger lover’s cock into my mouth. An immediate shock came over me yet without skipping a beat I did what I knew should be done and I started performing oral on him. Still shocked and confused I just kept sucking and gagging as he was at least 8” long and girthy. Jessica with her hand on the back of my head giving the initial push as well starting it all off. I didn’t finish him off that night, I only got him hard for her as she said “Babe please just get him hard for me that’s all you need to do right now.”
Thus, began my sucking her lovers off before and after sex with Jessica. It was a new world I never expected myself to be open to. The next morning after that first time sucking one of her lovers was another revelation. Jessica wakes me up and with some sweet kisses and rubbing her hand and fingers over my crotch. The sensation obviously woke me up from my dead sleep.
Jessica said “Babe, oh my God! Last night was the best ever!”
I answered, “Yes, it was pretty crazy, wasn’t it?”
Jessica was beyond happy and excited. “I can’t believe it, I just never expected you to do it but when I told Brandy how much better you were eating my pussy when there was cum in it she said you would definitely suck cock too! She said if I thought you really enjoyed it that much then to do what I did last night and for sure you would not stop or hesitate to suck his cock.”
Of course, I was not the happiest about that little part. Even though Brandy was her best friend I still was not the most comfortable with her knowing so much of all this about Jessica and I.
Jessica could see the annoyance in my face and said “Ok ok, I know what you’re thinking and I know you don’t like me always sharing everything with Brandy, but look how great things are now and it is thanks to her advice. I actually was gonna suggest that tonight we have her over to hangout. I think you and I should celebrate and as a present to you for doing all this and it going so great, I want to have her join us in a threesome.”
I shook my head in shock. “Say wha….? Wait, so you are into girls too?" I asked.
Jessica responded simply with “No not really. I have kissed girls just for fun out at bars but that’s it. I just want to give you something I know most guys want as a thank you for all this.”
As crazy as it may sound, I told Jessica “Sweetie you are all that I need and could want. I don’t need anything more or anyone else.”
Jessica smiled and said “Brandy said you would say that. I kind of thought so too but thought you at least deserved the offer. I mean you really are the best boyfriend ever.”
I would love to say that Jessica and I lived happily ever after but, as life would have it leaving college and having separate career goals and desires in life as far as what we wanted just didn't work out. We both left college and went on our separate ways. Jessica and I kept in touch for a few years after just formalities really of catching up and seeing how one another is doing. I believe she is now married with children living the happily married life. We lost touch after her engagement. I didn’t know it then and I don’t think Jessica did either but ethical monogamy sure but what we had back then was more along the lines of a full-blown cuckold relationship.
I hope this blog post was an enjoyable read. I am not a writer by any means but I did my best to tell a short story and keep it brief. I hope to see your comments and will gladly respond to as many as I can and answer any questions if any.
