My Unlikely Cucking
May 11, 2023 // By:analsex // No Comment
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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 for college, I was very much the closed-minded, ultra-conservative, super religious guy. I was a very anti-homosexuality, anti-interracial relationships sort of guy too. I dated around a little but it wasn’t until the first major relationship in college that turned my life around.It started 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 and a 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 wanna 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 me, 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 her hair and head around and there were those blue eyes of hers. She runs up as she catches me in the 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 two of her friends.So 5:45 pm 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 concerning 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 love Ümraniye Escort 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 of 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 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 exclaimed. 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 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 nonmonogamy. I sat up almost immediately with that revelation. Jessica obviously noticed the anger in my face.I began to say, “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 nonmonogamy.” She was right I totally missed that.So, I ask her, “What in the hell is that?”.Jessica continued 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 except 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. That 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 Ümraniye Escort Bayan with was not a conversation to be had at all with anyone. I was stuck in a whirlwind of torment and torture as to 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 the worst that could happen is that doesn’t work and we break up. I struggled greatly the first couple of weeks. Nothing 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 2 am 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 4 am Jessica sneaks in and slips into bed with me.I woke up that morning around 8 am smelling her hair on 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.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 run into a guy she knew from high school and had always kind of had a thing for. She continued 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 Escort Ümraniye 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? Oh My God!? Yes, you are! Babe, you are getting all hard! Oh My God, this is great!”I couldn’t lie or hide it. I mean I was sitting there in boxers and athletic shorts.Jessica said, “Oh my God 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 began to change at this point. Jessica and I immediately wasted no time concerning my excited state. I would say it 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 completely see it now. I could now see beyond my view and feelings afterward. There was a lot more happening in our relationship than I could ever have imagined.We talked afterward 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 bullshit 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 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 an actual choice in the matter. Jessica could sense that I was in and immediately just told me to come to pick them up around 8 O’clock. Saturday came and as requested I showed up to pick up 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, a super tight almost see-through 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 two 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 it 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 took a chair and set 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.Brandy 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.
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