Solace for His Breaup

Shout-out to an awesome writer Tomass and his "Becoming His Girl"-story which was posted here almost 20 years ago. I was greatly inspired by that story and all the credit of the original idea goes to him.

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I was devastated. My girlfriend Wendy had just told me that she thought we should be seeing other people. Or even bluntly that she wanted to see other men. This completely shook me off the balance and in a haze I returned to my apartment. All I wanted was to be alone with my pain but my new roommate Dwight was there. He didn't know me that well yet but he could easily see that something was bothering me. I told him everything and even shed a tear on my lost. I felt so miserable. I was little surprised how well Dwight was able to comfort me. He even gave me a big bear hug. I did not see that coming since being this six foot three pro athlete type of a guy my first impression of him had been more of a tough guy.

He got me settled down and even promised to talk to my girlfriend about this whole issue. Maybe there was some way to salvage the relationship. I considered this a little of a long shot since Wendy and Dwight had seen each other only briefly couple of times but I was willing to grab any change of getting her back and Dwight ensured me that he really knows how to talk to women.

Next day he really did go and see her in this local coffee shop. I was eager to hear the news about how it went and when Dwight returned I immediately shoot him with a bundle of questions. He told me there were some good news and bad news. I decided to get the bad news first and he told me that Wendy still wanted to see other people and would not budge from her position. The good news on the other hand, and Dwight was smiling broadly when he told me this, was that she had agreed that the first person she would go to a date with would be Dwight himself.

I must say I was not expecting this to be the good news. Dwight was physically just about everything I was not. Tall alpha type of a guy with broad shoulders and manly but symmetric face. And thus in my opinion the absolute nightmare date for my Wendy. I blurted this all out to Dwight hysterically. He explained that I did not understand his idea. Since Wendy anyway wanted to date someone wouldn't it be better it was someone I knew and who could tell me how did it go. Maybe he could even make it a bad date and try to make Wendy see what a polite and nice guy I was. I still was not completely sure about this plan but there really was nothing else to do.

However at the day of their date it was Dwight who came to me with some concerns. He said that the matter was little delicate and wanted to talk about it in his room. He was in his boxer shorts and was selecting some clothes he would be wearing for the date with my girlfriend. Even though we did have quite relaxed atmosphere at our apartment and I had seen him half naked before now that there was this date with Wendy coming up I was not able to miss the fact that Dwight had and incredible body. The muscles were prominent and to my embarrassment I caught myself even glancing at his crotch which in my opinion looked really intimidating. I thought I could see the outlines of his cock and it definitely was completely different from mine. My cock did not even create a clear bulge to my underwear and was most often just pointing to some weird direction a little bit. His was bending downwards looking like a python trying to break out free from his stretched underpants. So it is safe to say I had serious doubts about this whole date thing.

But anyway Dwight proceeded to his topic. He told me that he hadn't had a date in couple of weeks since he had been so busy and his "friend with benefits" had been out of town so he was unfortunately feeling quite horny. And since Wendy was very attractive young woman he was starting to worry. What if things would get out of hands? What if he was not able to resist Wendy? This of course was my worst fear. But I was glad he had the decency to talk about it and thanked him for his honesty. I didn't have a clue on how to solve this problem but Dwight on the other hand told me that he has an idea if I am willing to keep an open mind. I told him that I would do anything if there was a solution to this problem.

But when Dwight suggested that we would watch porn together and I would give him a hand job I bursted out laughing. I thought he was pulling my leg. But then I saw in Dwight's face that he was dead serious. He even went further on and coped his balls and explained that those babies were just too full of cum and some release would be needed just to be safe. And now that I realized he was serious about it I stumbled in my words but told him that I do not think I was able to do it and that I was not gay or even bi-curious. He said I was talking nonsense and that I should consider it like a massage. Nothing gay about massages, right? I still considered it to be clearly gay but he added that in the end it would very well be the question about is it going to be me or Wendy stroking his cock tonight and that it would be completely up to me.

The thought of Wendy touching someone else's manhood sting inside of me so badly that with some doubts I complied. Dwight seemed happy or even eager and put some pornhub flick on. Then he without further ado removed his shorts and this big lump of meat came to my view. I must have stared since he grinned and commented "Impressive isn't it?". I was out of my words but quite soon we were sitting at his bed. Watching the porn. Dwight leaned back and took a comfortable position and I could see that his cock had started to grow. What are you waiting for asked he and made a significant look to me and then to his own genitalia.

The porn was about some short haired brunette housewife kissing with this black porn star in a kitchen. During the kissing her hands trailed to the actor's trousers and dug out a humongous hard cock. I must say the scene was very hot and caught in the moment I also moved my hand and took a tentative hold on Dwight's cock. And if it had looked big it felt even bigger in my hand. It was hard to imagine but his cock was over twice the size of mine. Both length and girth. And how heavy it felt. I was feeling some melancholic jealousy realizing that I could never compete with this sort of cock if that was what the girls appreciated.

I stroked his dick up and down and it was getting harder but Dwight was not completely satisfied with my efforts. So he started to give me instruction on how I should use both hands and also fondle his balls. As you may have guessed his balls were big and heavy as well. He wasn't lying when he told me that his balls felt awfully full. Because they sure did. I tried to be as clinical as possible with my stroking but have you ever tried to stroke your buddy's cock and balls with two hands while he is lying in his bed? I kind of had to some extent crouch over him from the side resulting in this position where his cock was pointing directly to my face. I did watch the porn but since Dwight did not see my face from his point of view I took some liberties in checking his cock thoroughly. The mushroom head of his cock was flexing bigger and I marveled at it's smoothness. And the size of the whole thing was also really something to wonder.

I guess I was doing better job since he started slowly undulating his hips. Kind of fucking my hand. And I also could see and even smell that some amount of precum was starting to wet the tip of his cock. I looked the porn and the milfy brunette had dropped to her knees and was now lovingly sucking the pornstud's member. I compared the cock in the video to Dwight's cock and they looked quite the same. It seemed impossible to fit such a huge tool to one's mouth but the brunette was doing it ever so skillfully. As if Dwight would be reading my mind he whispered with deep and horny voice that what if Wendy would offer him a blowjob instead of a hand job. Seeing this perfect blowjob on the screen he probably would not be able to resist such offer if he haven't gotten one himself in few weeks.

I saw where he was going with this. And the same reasoning applied with the blowjob than with the handjob. I truly believed at that moment that it would be I or Wendy doing this tonight. And I closed my eyes and opened my mouth and with a little upwards thrust from his hips Dwight's cock found it's target and was penetrating past my lips. "Watch the teeth" he grimaced and I somehow had to unhinge my jaw to make room for the intruder. I was completely clueless on how to do it but started to move my lips up and down on the head of his shaft. He moaned and apparently he was pleased with my efforts. I tried to cover as much as possible with my lips and tongue since he had already warned me about letting my teeth to hit his flesh.

Quite soon my neck and upper back was becoming really tired since I was crouching towards him from the side. When I told he about this he just maneuvered me to the lower end of the bed so that I was facing him between his legs. So now this was becoming a serious blowjob and not just fooling around. I couldn't even see the straight porn anymore so I was having very mixed emotions having his member in my mouth and watching his upper body from an angle I have not ever seen before. He had these curly black pubic hair that reached all the way to his navel and I thought that girls must find those very erotic.

He shifted his thighs on the both side of my head and I was now literally very tightly between his legs. If this wasn't enough he also placed his hand firmly on the top of my head and really started to guide my efforts. Cup the balls with you hands he hissed with a low voice and I timidly complied. I used one hand for each testicle and he murmured approvingly. His cock and especially the bulbous head was really flexing inside my mouth and I could taste his precum flowing with every suction I made. It tasted salty. Every time I moved upwards making this vacuum with my mouth his cock swelled to new proportions and each time a little more precum oozed out from the tip.

So I figured out he was going to cum quite soon. I certainly did not want him to cum in my mouth so I started to withdraw in order to jerk him off but he would not have any of that. His hand on my head grabbed my hair and his grip was like iron. I stopped doing much but he was clearly on the edge and was pushing his cock in my mouth and pulling my head down. I gagged and tried to speak to him about the fact that I did not wish him to cum inside but since my mouth was pinned so tightly around his veiny and large penis I just made these obscene unintelligent sounds.

He on the other hand started to blabber with eyes closed. "That's right Wendy. Make your man happy. Take it all bitch. Your mouth is the best. Don't stop." I was aghast. He was clearly imagining himself doing this with my girlfriend. And now that he had made the comments even I had a vision of him and Wendy like this. How would her small mouth accommodate such a monster of cock. How her pretty auburn hair would look in his tight grip. Would her eyes pop out when he would fill her mouth. I felt like I was betraying myself but I also noticed that my own dick was hard as rock.

His whole body arched as he forced his cock too deep in my mouth. And then he started to shoot his semen in. It started with this powerful several seconds stream of cum and then subdued to the normal spurt after spurt which completely flooded my mouth. I both swallowed but also unintentionally let some pour out from the corners of my mouth. Some ended up even in my nose as I was almost drowning to his cum. There was so much of it. In my mind I pleaded for it to stop but it did not feel like it. It was like some weird stream of porridge filling my moth and eventually my tummy.

And finally it was over and he relaxed. In a somewhat similar manner like just before his actual orgasm his cock continued to leak cum. His grip on my hair was no longer as demanding but it was still firm enough to let me know that I was not supposed to leave his cock yet. So I gently made some slow and deliberate sucking motions as his cock was getting softer. And eventually he somewhat dozed off and I let the cock slip out of my mouth. It slapped towards his belly still huge and swollen. I stared it at moment and deep down admitted to myself that that has just been the most intense sexual act of my life. I also stared at his balls and felt ashamed that we had just tried to empty those big sacks in order to make Dwight more docile for his date with Wendy.

Later that evening when Dwight returned I was eager to hear how did the date go. But he promised to tell me about tomorrow and just went to bed. And when tomorrow came he slept long and when he woke up he had to hurry to some basketball training he had at that day. I tried to do some studying but it was really hard to concentrate. When Dwight returned from his training he could clearly see that I was eager to know but he still just hit the showers.

When he returned in his bathrobe all cleaned up I could no longer hold myself but cornered him in his room and started pestering himself about Wendy. Hi just told me that everything was good and that my preemptive efforts last night had not been fruitless but on the contrary he had been most pleased. I blushed strongly about his selection of words and he had this shitfaced grin when he was looking at my embarrassment. He sat on the edge of his bed and opened his robe and legs. His cock came to my view and I could not believe that I had had that thing in my mouth just yesterday.

Then he matter of factly said that he was going to go out with Wendy again tonight and signaled with a look and a nod towards his cock that he expected me to repeat my performance from the day before. I was terrified but he reminded me about the situation by saying that I really should not take a change of sending him with full balls to Wendy. And like before I agreed by falling down in front of him and tried to take his cock to my hands. "No hands" he stated firmly with low and commanding voice. I hindered but with some lingering moments closed my eyes and proceeded to his cock with my mouth. I was in all fours in front of him and there was no handjob foreplay or the porn like yesterday so for a brief moment I was thinking that this at least was really gay of me. But then I thought about Wendy and how Dwight had said that last night my efforts did not go in vain so I continued.

His cock grew in my mouth but quite soon I felt him reach over me and with both of his big paws he grabbed my ass cheeks and started to manhandle those through my pants. It did not feel that bad so I let him continue even though I simultaneously was thinking that this was all wrong. His cock was soon very hard and big again and like in some sort of trance he commanded me to loose my clothes. With a mouth full of cock I stared at him in disbelief. He sternly said that I did not want to make him repeat himself so I stripped naked in front of him. Hi pushed me back to the position and unceremoniously inserted his cock to my mouth. I don't know where did he find a bottle of lube but suddenly he was reaching over my back pouring some into my ass crack.

I whimpered as his fingers probed my rectum but all my objections were muffled by his cock in my mouth. Then he rose and pulled me up from my hair just enough to push me to his bed face down to the matrix. And when I landed there he followed immediately close behind. His big torso pinned me down and in horror I felt his cock between my ass cheeks. And then between my legs violently pushing against my balls and dick and the bed. "Please no" I whimpered but he was mounting me with purpose. He was biting my neck and then ear and I never forget his voice as he whispered in an out of breath voice "You have been asking for this Wendy and now your going to get it."

So he was again in his zone imagining me as Wendy. I tried to struggle away but him being five inches taller and significantly heavier than I it was a lost cause. He just pinned his arms around my shoulders and stopped me from running away. His lower body followed also but this time his cock did not go between my legs but hit right to the spot on my well lubed anal opening. I yelped even though I soon learned that that was not even his dick going in yet but it just somehow pushed my asshole deeper between my cheeks as the blunt head was denied entry by my tight virgin hole. But it was like some undeniable battering ram which could not be kept out for long.

"Little Wendy. Are you a virgin? Let the big bad wolf in. Let's make some love. Let's make babies." He was whispering these things that did not make sense to my ear I guess mostly to excite himself. All the time his demanding cock was urging my asshole to surrender. I thought of his cock and remembered that even though the girth was intimidating all along the shaft the mushroom head of it was probably the fattest part. So in my inexperienced opinion this would be the most unsuitable cock shape for anal sex. However Dwight seemed to disagree as he was happily humming and relentlessly proceeding forward where no one had gone before.

As my anal ring was opening so was the pain increasing. Still the head was not in but the pressure was just violent. "Little Wendy there's a party in your asshole and my cock was definitely invited. Why don't you let me in? But go ahead and resist. It will not make a difference. It excites me even more when you virgin butt makes up a fight. Soon Wendy your hole will be caressing every inch of my cock ever so sweetly. Oh fuck your tight". Dwight was in no hurry and was enjoying every second of it.

But I was not. I was desperate to make the pain go away. In some false hope I was thinking that maybe I should try to push it out with my butthole. But apparently this is just what helps it in further. So in slipped the porn size cockhead and I yelped in agony. "Please no. Take it out. It hurts. You are too big. Please stop." Nothing helped. Dwight just continued. "Little tight but Wendy you'r doing just fine. You have no idea how wonderful this feel." The first inch and a half were in and rest would soon follow. I had kept my legs closed but they didn't stop the attack from behind. Dwight wanted even better access and he spread my legs wider apart with his own powerful legs. I wasn't going anywhere so he shifted his arms from my shoulders and took a hold on both of my loins. Pushing his own pelvis forward and pulling mine backwards he penetrated deeper. My pleads for mercy had subdued into more of a wordless whimpering.

So there I was. Pinned to the bed by this hunk. His hot lips on my neck and his vulgar grunting in my ear. Legs spread awide and ass pulled up. With every thrust his cock was invading new territory inside of me. My asshole was throbbing in pain but I guess even that just increased his pleasure. He continued to be very vocal and thanked me, Wendy, for the best date ever. And that he would be glad to be a steady couple as long as he would have free access to my plump tushy. His pushing had been demanding from the beginning but I could also feel that he was picking up the pace. I guess some of my whimpers sounded a lot like moaning.

When I thought the worst would be over he rose and pulled me to all fours without completely leaving my ass. "Arch your back bitch" he just ordered and to make sure that I did he pulled my head up from my hair and with the other hand gave a firm slap on my other ass cheek. When he was satisfied with my position he started to saw in and out with gusto. He altered short pushes while being almost fully inside but also similar short pushes where the rim of my asshole was milking the girthy knob of his cock. But finally the main event was the lengthy full thrusts where he went in and out with the whole might of his big cock and truly owned my ass.