Becoming Melissa's Cuckold Pt.10 free porn video

I wasn’t happy to see Tayshaun. I didn’t like the way he treated or spoke to me, and I was also worried that Melissa was spending too much time with him. I accepted her sleeping with other men, but I felt like Melissa and Tayshaun were getting too close, doing things like going shopping, grabbing dinner or catching a movie. At the very least, those were the kinds of things that I wanted reserved for me. As crazy as it might sound, I would have rather that Melissa had gone upstairs with Jessica and those 3 other guys than for her to spend another night with Tayshaun.

Melissa brought Tayshaun up to the deck, he seemed to already know some of the guests but she introduced him to a few others. I stood there jealous and brooding watching them for nearly an hour. In addition to everything else, I was mad that Melissa didn’t look at me once the whole time.

The shlubby guy hit my shoulder and pointed to a light flickering on and off up on the second floor of the house. “Can you give me a hand?”

“With what?”

“The flickering light. My wife and Demarcus were in there, the flickering light means that they’re done. Others are going to use that room, it’s my job to change the bed sheets and clean up the room. I could use a hand flipping the mattress over.”

No part of me wanted any part of doing that, but it did give me a reason to get away from watching Melissa fawn all over Tayshaun.

“Ok, I’m not cleaning anything but I will help you flip the mattress.”

The shlub seemed to know where he was going. He walked me past the deck and the back entrance to the house – I guess that was for women and bulls only – and took me to a side door. We opened the door, stepped inside and were immediately greeted by the sounds of fucking. Even from the ground floor, various moans, grunts, screams, slaps and other sex noises could be heard coming from the second floor bedrooms.

“I guess not everyone is finished,” joked shlubby guy.

There was a staircase at the back of the house that was near the doors that lead to the deck, but we went to the front of the house and found another set of stairs there.

“This way is a little longer, but trust me,” the shlub said with a knowing smile.

As we climbed the stairs the unmistakeable sounds of fucking became louder and louder.

“My wife’s room is at the back of the house, but we’ll have to walk by these other rooms to get there. Don’t stare, but sneak a peek!” His reason for taking the front stairs became obvious.

Just a few feet down the hallway on our right was an open door. Before arriving at it, I heard soft moaning sounds. I slowed my pace as I walked past the door, turning my head towards the room as I walked by. Inside, Jessica was on the edge of a bed in the doggy position. She had a guy standing behind her working his cock in and out of her pussy and another was on his knees in front of her while she sucked his enormous cock. The third guy who she’d brought upstairs with her was sitting in a chair catching his breath, covered in sweat. He’d already had his way with Jessica.

A few feet further down the hall on the opposite side of the corridor we walked past another open door. Casually peering in, I saw Phillip standing by the foot of a bed while a topless Diana took his cock in her mouth. Phillip saw me, made eye contact and nodded ‘hello’ as he reached for the door and closed it as we walked by.

The shlub stopped at a closet and grabbed a set of sheets that had been folded and stacked there along with several other sets, 10 or more in total. Clean sheets in hand, we rounded a corner that would lead us to the back bedroom but were met by the shulb’s wife Elaine and her lover Demarcus. Elain was still naked. Demarcus wore only a towel around his waist. Elaine was really cute, the shlub was definitely punching over this weight with her – not unlike I was with Melissa.

“Aww, thanks honey!” the much shorter Elaine reached up to kiss her husband. I could only imagine what had been in her mouth, and now his. “Everyone’s probably naked by now right? No point in getting dressed. We’re going to skinny dip.”

“Have fun dear,” he said to his wife before turning towards Demarcus, “and thank you for taking care of Elaine. It’s been a stressful week and she really needed that.”

“The pleasure was all mine,” Demarcus said with a deep voice and a Caribbean accent of some sort.

We entered the back bedroom and while I wasn’t sure what to expect it wasn’t the mess that I thought it might be. The smell of sex and sweat definitely hung in the air, but other than the messed up bedsheets the room didn’t really require much cleaning. I watched as the shlub pulled off the damp and sweaty sheets off the mattress, then helped him flipping it over. The shlub put the fresh sheets on the bed then did a quick survey of the room – flattened the carpet where it corner had rolled up, fluffed the pillows and emptied a trash can that was beside the bed. Reaching in, he pulled out a condom – one big enough that I’m sure I could have fit my arm into. The shulb pointed to the massive load inside.

“Look at that, he fucked the shit out of her!” He was proud of his wife.

By the time we made it downstairs and out to the back yard, the party had picked up a gear – I guess prompted by Elaine’s insistence on skinny dipping. All of the women were topless, including Melissa and a few of them were totally naked …not that any of them were wearing swimsuits that covered much in the first place.

Melissa and Tayshaun were still a part of the main group, but they’d separated themselves a bit. Melissa had had a few drinks by this point and she was looking at Tayshaun in a way where I knew the inevitable was going to happen that night.

The shlub and I made our way to the back half of the yard where ‘our kind’ was permitted to be. Before I could feel too sorry for myself, I found something to be grateful for – I wasn’t Mikey. Kassandra and Charles, both naked returned from inside. Walking at Kassandra’s side, on all fours like a dog was Mikey. To further emphasize his position, he was collared and she had him on a leash. His humiliation didn’t end there though. She walked up to the deck – the first of us who’d been allowed on the deck – and everyone stood around laughing at him.

“Bark puppy!” Kassandra commanded.

Mikey attempted to bark but only a muffled sound came from his mouth. He looked like he might be choking.

“I said bark puppy!”

Again, Mikey tried without much success – at least not to Kassandra’s satisfaction.

“What’s the matter puppy? Is something in your mouth?”

Mikey shook his head ‘yes’.

“Let’s see then” and with that Mikey opened his mouth as Kassandra reached inside, pulling out a used and still full condom.

“Aww, puppy…when I told you to eat it I didn’t mean the whole condom, just the delicious load inside!”

We all knew what was coming.

Kassandra lifted the condom above Mikey as he tilted his head back in anticipation.

“Open wide!”

Kassandra turned the condom upside down and used her fingers to squeeze and push Charles’ cum out and down on Mikey’s waiting tongue.

“Good boy, now swallow.”

Mikey hesitated and looked like he was gagging and might throw up.

“Don’t you dare spit that out. Swallow it.” Kassandra watched as Mikey struggled to follow her commands.

“Mummy worked hard for that load. Her poor little pussy took a pounding from a big black cock so that you could have that. If a single drop of it leaves your mouth, you’re going to suck Charles’ cock so he can give you another load to swallow.”

Mikey was still gaggling and struggling to swallow, but clearly took Kassandra’s threat seriously. He finally gained his composure and in one motion braced himself and swallowed hard.

“Open up, let me see…is it all gone?” Kassandra inspected his mouth and appeared to be content. “Good boy, now run along and join the other fucktards.” Still in dog mode, Mikey crawled his way back to our section of the party, dragging his leash behind.

As weirded out I was over what Kassandra just made Mikey do, I found everyone’s reaction to it equally strange – they all treated it as if nothing special had happened, like it was no big deal. The women on the deck looked at Mikey with an expression of awe while looking at Kassandra with admiration. The bulls did their best to not react, but they couldn’t hide their contempt for Mikey. The guys that I was with gave him a look of empathy, perhaps because in one way or another they’d been in his shoes before.

I also found it strange that the threat that Mikey faced was to suck Charles’s cock. Maybe that was an idle threat, but I was surprised that Charles didn’t react to that. I don’t mean to stereotype, but Charles was Jamaican and at that time anyway Jamaican guys weren’t exactly known for having enlightened views when it came to homosexuality. So much more happened that night that I’d forgotten about this until weeks later I remembered and asked Melissa if Charles was bi. She told me he wasn’t, but he’d been to jail and the black prison gangs used to punish white guys by making them give blow jobs. To Charles, it was more about punishment and humiliation that anything sexual for him. I hoped Melissa never hooked up with him, and luckily she didn’t.

Back to the night of the party with the show that Kassandra and Mikey put on over, the party returned to its former state, albeit it a little louder now as more and more of it was fuelled by alcohol. I should have been in haven with about a dozen naked or half naked women running around, playing in the pool and shaking their tits just for the reaction but I couldn’t take my eyes off of Melissa…not her exposed tits, but the fact that she and Tayshaun were increasingly close in a way that I didn’t like. I was getting upset, not because I knew that he was going to fuck her but because I was afraid that she might love him.

They began making out up on the deck and after a few moments Melissa looked over at me, the first time she’d acknowledged me since Tayshaun arrived. She waved at me and pointed to the bottom of the deck stairs, motioning for me to join her. I made my way to the bottom of the stairs where she met me, Tayshaun hung back.

“You doing ok?” she asked.

“Yeah, I guess so….”

“I meant your penis. You’ve seen a lot of things tonight, is your little guy hurting?”

I’d been so distracted by everything and trying take it all in that my dick never really got beyond the near constant frustrated state that I was used to being in. But if Melissa was offering sympathy, I wasn’t going to look a gift horse in the mouth.

“Yeah, it hurts. Do you think you could let me out?”

“No, not now. We’re about to go have our fun. I’ll tell you what though, if you behave – no attitude, no whining, no sulking – something special might come your way…the advice that Kassandra and Diana gave me earlier this week. I’ve decided to go through with it. Trust me, that’s good news for you. All you have to do is behave yourself, ok?”

“You can’t tell me now?”

“No, you’re going to earn it by being nice tonight.”

“Ok.”

With that, Melissa motioned for Tayshaun to come join us and the three of us gathered beside the deck. Without saying a word, Melissa led us around to the side of the house using the same door that the shulb husband brought me to earlier. Once inside, instead of going upstairs Melissa led us downstairs to what looked like an entertainment room. It was set up with a giant tv, a pool table, some old pinball machines and a bar. Towards the back of the room there was a couch facing a bed.

“Why don’t you get Tayshaun and I some drinks?” Melissa said to me as she pointed to the bar. The two of them continued to the back of the room where the bed was waiting for them.

I fumbled around behind the bar, not really sure what to bring them but I found a beer for Tayshaun and a glass of wine for Melissa. The two of them were now on the bed, Tayshaun sitting on the edge with Melissa on his lap as his hands wandered her body. I’d heard Melissa have sex plenty of times, but if I was expected to stay and watch what was about to happen it would be my first time seeing her have sex. I hurried up in bringing them their drinks, hopefully giving them something else to focus on would delay the inevitable.

By the time that I got to them, Melissa had clearly forgotten about the drinks. She and Tayshaun were locked in a long series of kisses, he held her in place as she wrapped her arms around him. I just stood there beside them with a drink in each hand waiting for either of them to notice me.

Without even looking at me, between kisses Melissa muttered that I should put the drinks on the table “for later”. I followed her instructions, putting a drink on each of the bed’s two side tables. By this time Melissa had made her way down to her knees and was undoing Tayshaun’s shorts. I really wasn’t sure what I should be doing – did Melissa want me to watch this? Did she expect me to leave? I stood there confused, or maybe mesmerized really not sure what I should do. It was beyond awkward.

As Tayshaun lifted himself enough off the bed to remove his shorts, Melissa looked at me for the first time.

“Take off your clothes. If we’re naked, you’re naked.”

I’ve already described a few instances where I’ve looked back on things and see them as defining moments and this was yet another one. Even at the time I knew that the decision that I was about to make would change things for me, one way or the other. I did not want to get naked with them. I’d just seen Mikey get humiliated and wanted no part of that. There was no way that I could stand there watching my girlfriend get fucked while I was locked in chastity and not feel like a loser like the other guys I’d seen outside and spent half the night convincing myself that I was nothing like. I also knew from Melissa endlessly talking about Tayshaun’s cock that he was much bigger than me…I was already self-conscious enough that I didn’t need to see any direct comparisons. I had all of these things running through my head, certain that this would be the time that I put my foot down and put an end to all of this…but I didn’t. Just like always, I did as I was told and I took my clothes off.

Melissa could tell that I was hesitating and the look on her face when I gave in said everything. If she had any doubts, she knew in that moment that she had me and whatever she had planned for us, I was going to go along with it.

“Come over here,” Melissa said pointing beside her. My knees were shaking, but I made my way over to her.

“Don’t stand above me like you’re a real man, get down here”

I lowered myself to kneel beside her. I was so nervous I wanted to throw up. Without saying a word, Melissa leaned in to me and gave me a long kiss. I didn’t want that to end, but she pulled herself away from me.

“I need you to see this so you understand.”

Before I could make sense of what she meant, she reached over to Tayshaun and pulled his boxer shorts down, revealing his massive cock. Melissa grabbed it by the base with one hand. If she’d grabbed it with both hands they still wouldn’t have covered the length of his cock.

I’d avoided looking at Tayshaun up until that point, but sensing him looking down at me we made eye contact for the first time. He was loving this. Where I was nervous, sick, anxious and confused he was totally in his element with a giant smile on his face, almost laughing at my predicament while he enjoyed his.

Melissa stroked his cock a few times then leaned in and wrapped her lips around the black monster. She struggled to open her mouth wide enough to get it in. Of all the things to think about in the moment, I’d recently seen a nature video where a snake dislodged its own jaw to swallow something larger than its mouth. The way was straining to fit Tayshaun’s massive cock in her mouth, the snake video was all I could think of. She did her best with it, then turned to me opening her mouth to kiss me again. I wish that I could say that I turned away, left and put the whole episode behind me but I didn’t. I leaned in and kissed her. When broke off her kiss she had a huge smile on her face.

Her hand continued to work the length of his cock stroking it.

“This is what I need Grey, not…” she didn’t finish her sentence, instead she let her eyes drop down to my locked up penis.

Tayshaun wasn’t interested in whatever was happening between Melissa and I. He gave me a slight push, knocking me off balance and told me to go sit on the couch. He’d had enough of me. Melissa immediately resumed sucking his cock.

From where I sat, I could only see Melissa from behind as she bobbed up and down guided by Tayshaun’s huge hand on the top of her head.

It had been over a week since I’d been let out of my chastity and all of that frustration along with everything that I’d seen so far this night combined with what seemed like a live-action porno in front of me became too much to bare. My penis strained against its cage in the worst way imaginable. Remembering how good it felt to have Melissa run her tongue across my balls made watching her give Tayshaun a full and proper blow job all the more painful.

Melissa sucked and slurped on his cock for what seemed like forever but was probably only a few minutes. I could tell by some of the noises coming from her that he was forcing his cock down her throat almost choking her with each thrust. Wanting more, Tayshaun stood up - his cock still in Melissa’s mouth - he lend over and picked her up off the floor lifting her into the air and playfully threw her down on to the bed where she landed with her legs spread apart. She reached for the string-tie of her bikini bottom and undid it, letting it fall down one of her legs but not quite falling off completely. Her bikini dangled around her ankle just like the key to my chastity did.

Melissa’s eyes were locked on Tayshaun. I think that she’d forgotten that I was even there. He moved between her legs, positioned himself and I could tell that he was moving his cock up to Melissa’s pussy. He must have been teasing her with it because in a rare change of roles I actually heard Melissa beg.

“Please…please give it to me. I need it.”

“You want my cock?”

“Yesssssss….please….I’ve waited all week, I need it sooooo badly!”

Satisfied, I could tell that Tayshaun had pushed his way into Melissa by the loud moan that she made. I watched from behind as Tayshaun adjusted and re-adjusted himself, moving his hips in a way that made me realize that he was pushing hard to fit his cock into my girlfriend’s pussy. For Melissa’s part she just laid there with her legs spread, bracing herself with her hands on Tayshaun’s shoulders moving in synch with him as she took in his big black cock.

It took a while, but after a few seconds of the two of them moving to accommodate each other Tayshaun seemed to be all the way inside of Melissa. She was no longer pleading with him but the look in her eyes as she looked up at him did the begging for her. Tayshaun paused for a second, then began to work his cock in and out of Melissa. Slowly at first giving Melissa a chance to adapt but he steadily increased his rhythm alternating between long full strokes with quicker short ones. Melissa just resigned herself to his control, laid back and let him do his thing.

While seeing all of this was difficult for me – both emotionally and because I was locked up – what struck me the most in the moment was seeing a submissive side to Melissa. With me she’d always been very dominant and in control of everything. With Tayshaun she was much more at his mercy, he was taking from her what he wanted and she was letting him have it. I think it was then that I realized what Melissa meant by being a real man. In my head it was all about dick size, but it was much more than that. Even if I had a larger penis, I don’t think that I had it in me to take control of a woman like Tayshaun did. I was realizing that it wasn’t in my nature to act with confidence, to be strong and manly. It wasn’t just Tayshaun’s cock that Melissa needed. It was his strength and power – his ability to be a man and make her feel like a woman. Seeing this all play out in front of me made me realize I could never do for her what Tayshaun was. When she told me that I needed to see this to understand, I think this is what she meant.

Of course Melissa and Tayshaun were oblivious to the breakthrough in understanding that I was having. They were fucking hard. By this point Tayshaun had got Melissa up on her knees and positioned himself behind her giving it to her doggy-style. Now facing me, I think Melissa was reminded that I was actually there. She made eye contact with me and I think at first looked a little worried but I smiled letting her know that I was ok and she immediately slipped back in to pounding that Tayshaun was giving her.

“His cock feels sooo good Grey….it’s so big!” Tayshaun was fucking her so hard that she struggled to get the words out of mouth. She’d lost control of everything, even her ability to speak.

It would take me a long time to fully come to terms with what I’d just learned about myself, but there in that room I just accepted what was happening as much as Melissa was. Instead of being upset and angry I was happy for Melissa. I got it. She was getting something that she needed, and it wasn’t something that I’d ever be able to give to her. I wasn’t that kind of a man and never would be. I’d like to say that I became fully enlightened at the time, but it wasn’t like that. I was still jealous and insecure – worried that Melissa would leave me for Tayshaun. But I was able to bury all of those feelings while I was in the room with them.

Tayshaun fucked Melissa for several more minutes as I watched. When he was ready to cum, he pulled out, flipped Melissa on her back and sprayed a massive load across her stomach. He looked proud of himself.

Melissa laid there for a bit before tilting her head back towards me.

“Babe, can you grab me a towel?”

Earlier I’d seen a pile of towels stacked on the bar and knew what she wanted. When I returned with the towel, Tayshaun had already gotten up and was half dressed. He leaned down to give Melissa a kiss before announcing his departure.

“I’ll let you two sort your shit out. I’ll be in the pool.”

With just the two of us in the room, Melissa cleaned herself up but remained naked in the bed.

“So…” she began but I cut her off.

“I get it Melissa.”

“What?” she seemed confused.

“All of it. I get it now.”

“You’re ok?”

“Yeah, oddly enough I am.”

“Come here.” Her tone was more tender than it was commanding. I crawled into bed with her, trying to ignore the pool of sweat that they’d formed on the bed sheets. We laid together as I held her in my arms.

“You’re really ok with what just happened?”

I had to be honest with her. “Sort of. I mean, I wish things were different but watching you and Tayshaun kind of made me realize a few things.”

“Well holy shit! Dianne said this would happen and I totally didn’t believe her.”

“What did she say exactly?”

“She said that she knew your ‘type’ and if you went along with the smaller steps you’d accept the bigger steps as well. She thought it would take a while, but I guess not.”

“No more bigger steps ok? I’m still trying to wrap my head around this but I think I can deal with it, but no more ok? I might have accepted who I am tonight, but I’ve also learned who I’m not. As much as I’m not Tayshaun, I’m also not Mikey.”

“I can respect that.”

We laid together for a few moments holding each other and it was the closest that we’d ever been with each other. The fact that Tayshaun left so soon after having sex with Melissa also made me think maybe he wasn’t a threat to our relationship. It was all physical, there was no tenderness. I wanted to be with Melissa. He just wanted to fuck her.

Melissa twisted around in bed. I couldn’t tell what she was doing at first but after disappearing under the covers for a second she popped back up and placed my chastity key on my chest.

“Let yourself out.”

I was aching and didn’t need to be told twice. I got that thing off of me faster than I ever had before. Without even asking, I started stroking myself before Melissa stopped me.

“No.”

For a moment my heart sank. Then I realized what she had in mind. Melissa pulled the top sheet away from us and lowered herself down to my dick.

“Don’t be nervous,” she said and she took me in her hand. It was hard not to cum from her first touch. The next put me over the edge. Melissa leaned in and licked the length of my dick from bottom to top before giving the head a kiss. As soon as her lips made contact with my sensitive head, I exploded in orgasm. Embarrassed, I immediately started apologizing.

“I’m sorry, I’m sorry! It’s just been so long and I’ve been so frustrated and everything that I’ve seen here tonight…” I was rambling.

“It’s ok, it’s good to get the first one out of the way. You’ll last longer on your second one.”

Second one? That sounded good!

I was too young and too horny to lose my erection after cuming, plus Melissa continued to hold me in her hand giving me long soft strokes. She pointed to the mess that I’d made. “Some things might have changed tonight, but not everything. You know the deal. Eat up.”

Melissa watched as I used my fingers to scoop up the load that I’d just shot. The approving look on her face as she watched me eat my cum made it worth doing.

“It’s so fucking sexy that you do that for me.”

With that she pulled my dick back and without warning she took it in her mouth. If I hadn’t just came, I would have the second my dick felt the warm, wet hold of a woman’s mouth for the first time in my life. She gave me a second to adjust, then began swirling her tongue around the head of my dick and started sucking it.

I couldn’t believe what was happening or how good it felt. I’d waited my whole life for this moment, and not only was it happening but it was happening with one of the most beautiful women that I’d ever seen in my life.

I guess not surprisingly after just having Tayshaun’s cock in her mouth Melissa wasn’t have any problems with mine. Being smaller and an easier fit for her mouth, she was able to do more with it and although I’d just come a few minutes earlier I was getting ready to blow again. I wasn’t sure what to do, if I should let Melissa know or just come in her mouth.

“Don’t come in my mouth” she said apparently reading my mind. “Let me know when you’re going to come.”

She’d barely finished speaking when I had to warn her.

“I’m gonna cum!”

Melissa pulled her mouth away from me and stopped stroking.

“Don’t come.”

I couldn’t bare it and reached for my dick to give myself the few strokes that it would take to make me shoot again. Melissa stopped me.

“Grey, look at me. Don’t come. Not yet.”

It was absolute torture, but Melissa held my hands by my side and prevented me from touching myself and my dick twitched and pulsed but didn’t come. “Trust me Grey.”

Melissa waited for a few minutes before touching me again. Stroking me very lightly at first, then alternated between strokes and licks.

“Are you ready?”

“Yes! Please let me cum this time!”

“I will” Melissa smiled as she raised herself up, placing one leg on either side of me placing her pussy right above my dick.

OMG she was going to fuck me!

“Are you ready?”

“Yes! Please Melissa!”

It didn’t bother me that she was just with Tayshaun. In the moment it was the last thing on my mind. I was the last virgin among my friends and that was about to come to an end.

Melissa held my dick as she positioned herself on top of me, slowly and gently working just the tip into her warm, wet fold before finding the right angle lowed herself down on to me. I’d never felt anything better before or since in my life. She sat on my with my length fully inside of her.

“You ok?”

“Yes.”

“I’m gonna go slow.”

She raised herself up, I was nervous that I might pop out of her but she knew what she was doing and knew exactly how far she could go before lowering herself back down on to me. I didn’t last more than a few seconds before blowing my load into her. Melissa tried to cover her laugh up with a smile and a giggle. She stayed on me allowing me to feel the post orgasm bliss of being in side of her before pulling herself away and laying back down beside me.

“No more virginity.”

“Thank you Melissa. Thank you so much. That was incredible!”

“I told you that if you behaved yourself that something special would come your way.”

I took Melissa in my arms with the intention of holding her as I tried to make sense of everything that just happened, but she had slightly other plans.

“Did you forget?”

“Forget what?” I had no idea what she was talking about, so I guess I had forgotten.

“You know the deal…if you cum, you eat it.”

“But….it’s…”

“Trust me, it will come out. You’d better get down there now though.”

I really wasn’t sure about this, but I wasn’t going to ruin the moment – a moment that I’d remember for the rest of my life. I brought myself down to Melissa’s pussy, getting a close view of it. I’d seen her several times before but this was the first time I’d seen her after she’d gotten fucked. She was far more open and stretched out than I’d ever seen. I knew that wasn’t from me, in fact I wondered if she’d even felt me when I was inside of her. It was a stark reminder of everything that had happened – it was easy to forget in my post virginity euphoria.

Just as Melissa had said, some of my cum had begun to leak out of her. I licked the insides of her thighs and around her mound before dipping my tongue into her pussy lapping up what I could of my own cum. After a minute or so of licking and sucking Melissa seemed satisfied, tapping me on the shoulder giving me the ‘ok’ to come back up.

As I did, she held out my chastity device in front of my face. “Better get this back on too.”

“Do I have to?”

“Of course you do! A few things changed tonight but some things definitely didn’t and chastity is one of them.”

We spent the next hour or so in bed talking, mostly Melissa peppering me with questions about the night, how it felt to lose my virginity, what it was like to see her with Tayshaun etc. When we finally rejoined the party it had died down considerably. People were either inside doing their own thing or had left. Tayshaun was nowhere to be seen and Melissa didn’t seem to care. That was good.

We hung out for a bit before deciding to head back to the city. The two hour flew by. Melissa slept most of the way and I was lost in my thoughts the whole way. So much had happened that night, it was going to take me a long time to wrap my head around everything.

One thing was clear, the trajectory of my life and changed, at least in terms of certain lifestyle choices. I gained an understanding of what Melissa wanted and needed from men like Tayshaun and accepted that I couldn’t provide that for her. After losing my virginity to her, there was no way that I was going to break up with her. I guess by default that also meant that I was willing to accept my role as her cuckold.

The following day was far less awkward than I thought that it would have been. For the most part, it was a normal day. It was the weekend so we slept in, but eventually we got up, had a late breakfast – which I served her in bed – then got ready for the day ahead of us.

The time did come when we had to talk about what had happened the night before and we went over everything together. I bit of time didn’t change anything for me. I still thought that Melissa could have her thing with Tayshaun, and I was less bothered by it having accepted the things that I had in the wake of what happened.

One thing stuck in my mind that I didn’t to figure out though.

“Last night you said that you’d decided to go through with some advice that Kassandra and Dianne had given you. What was that about?”

“They both thought that I should have sex with you.”

“Really?” I was surprised to hear that, especially coming from Kassandra.

“Yup. I didn’t really plan on fucking you to be honest, like probably ever. I kinda liked things the way that they were. I didn’t know where things were going between us, but I was pretty sure that it wasn’t ever going to be there. They made me realize that it had to.”

That was a little upsetting to hear that. I’d thought about all of the things that I’d done to make her happy. I figured that eventually she’d value that and see how much I loved her and that would lead to a normal relationship. Apparently she had different plans.

“Why did they say that you had to?”

“Well, know that you what it’s like to be with me we can use that to push your boundaries. Like, before when you were in chastity you didn’t know what you were missing other than your hand. Now that you’ve had some pussy I think being denied will mean a lot more to you. Now you’re really going to know what you’re missing. I can work with that.”

This wasn’t sounding good at all.

“We’re still going to have sex, right? I mean like regularly, like a normal couple?”

“Umm…well…maybe? I guess it depends on what you mean. We’ll have sex again, sure. Regularly? I don’t think so. And we’ll never be a normal couple.”

“I’m really confused Melissa, I thought last night was a turning point for us? I told you that I’m ok with Tayshaun, I accept that he can give you something that I can’t but I still want to be able to give you what I can.”

“Yeah…but it’s not really about what you’re able to give to me. It’s about what I want from you and what makes you special to me. I can get boring sex – no offense – from a lot of guys. Men like Tayshaun take care of me sexually. I don’t need that from you. What I like about you is your willingness to sacrifice for me…wearing chastity, eating cum. Other guys don’t do that for me, you do. That’s what I need from you. Not sex.”

“So where do we go from here?”

“Nothing changes really. The only difference is that we’re in this lifestyle now – for good. You’re my cuckold, that’s it. You asked about sex, well what happened last night – that’s sex for us now. I get what I want from whoever I want and you get a little reward whenever I decide that you’ve earned it by behaving.”

That conversation set the tone for the next eight months or so of our relationship. Sex became a reward for me when Melissa was especially pleased with something that I did for her. Finding a new lover for her became great way for me to get in her good graces. She’d task me with meeting someone new for her, get to know him, let him know about our lifestyle and introducing him to her. If she approved, my reward would be to have sex with her – always after she’d been with her new man. In the entire time that I was with Melissa, not once did I have sex with her unless she’d just been with someone else first.

Its weird to say that such an unusual lifestyle became routine, but it really did. For the most part Melissa did as she pleased, and I did whatever I could to please her. The promise of having sex with her was all the motivation that I needed.

In the end, our relationship ended in the strangest of ways. We had a problem with our landlord and had to move out of our apartment on really short notice. We weren’t able to find a new place in time, so she moved in with Tayshaun and I moved back in with my parents while we did our apartment hunting. About a month went by without us finding a new place, but I’d lined up a bunch of apartments for us to go see one weekend. I called her at Tayshaun’s house to let her know about the viewing appointments that I’d booked and he told me that Melissa was gone. She’d gotten a job offer modelling in New York – something that had always been a dream of hers - and packed up and left without even saying good bye.

Twenty years went by before I ever spoke to her again. During that time I’d occasionally hear bits of pieces about her through our common friends. At one point she joined a band that got some buzz in New York and were a flash in the pan sensation for a year or so. Many years later, I awkwardly ran into Tayshaun on the subway once. He remembered me, but had gotten my name wrong calling me Gary. I was that insignificant to him. He hadn’t heard from Melissa since she left. I spent so much time worrying that Melissa would leave me for him, but she left us both.

A while back, I originally started publishing these stories on another website. Someone read one of the early chapters there, recognized my rather unique name and remembered that their friend Melissa once dated a guy named Grey. Melissa got in touch with me through that site. She was ok with me telling my story, but asked that I change a few names to protect her privacy. We spoke on and off for a while, but we’re both much different people now than we were when we younger and really had nothing in common any more. As I’ve continued to write this series, I’ve sent each chapter to Melissa as a courtesy before publishing them here. At first she’d offer a few comments. For the last couple (Chapters 8 & 9) she didn’t reply at all. I didn’t bother sending her this chapter.

Our relationship was relatively short in the grand scheme of things but it was and remains the most formative relationship of my life. It made me who I am and helped defined my private life. I’ve had several ‘vanilla’ relationships, and tried to make them work but I’m never able to truly find my comfort level in them. Melissa made me her cuckold, and being a cuckold is still how I most strongly identify as. In my two longest relationships after Melissa, I was cuckolded in both of them. But those are stories for another day.

A lot of people have asked me if this story is true. If it’s not clear by now, yes – it’s true, or at least a semi-fictionalized version of the truth. All of the events happened as described to the best of my memory. For the sake of brevity, the overall time line of the story was compressed. While these things happened, they didn’t happen one after another in quick succession and some artistic licence was used to form a narrative that made sense. Beyond that, this is a true story.

Writing this story has been a long process and I’d like to thank everyone who left a comment, sent me a message or otherwise offered support and encouragement. Thanks!