Cuckold Cleanup Stories: Your Buddy Gives You Valentine’s Day Advice for Your Girlfriend

I found it surprising that my girlfriend, Amy, and my friend, James, were so bold and comfortable talking about sex. James was telling her about the kind of underwear he liked to see his girls in and suggested a pair she should put on for me someday. I knew that James’s favorite thing to do during sex was to slide his big cock into a chick’s tight pussy while she’s still wearing her panties. He insisted I try it out someday because the feeling of silk grinding against your big dick as it goes in and out of a girl’s pussy is a feeling that couldn’t be described. He also claimed that the contact of panties against his balls made him cum harder than usual, and he loved to leave a mess and stain the girl’s expensive lingerie, just to leave his mark. I knew that he always made his girls wear pink because there was something symbolic about a man leaving cum stains on feminine underwear. James was quite the alpha male.

“It’s how you mark your territory, bro,” James joked. Funny enough, James wasn’t that passionate about his underwear. In any locker room we were ever in, I never saw him anything other than navy blue Tommy John boxer briefs.

The dialogue between my girl and my buddy somehow evolved into a discussion about places they had sexual encounters inside of. James said he always wanted to get head in a movie theater, and I told him how awesome that was, making my girlfriend chuckle, saying she’s never done that for anyone before. I told James that it wasn’t with her, as her comment made me look like I was lying. My girlfriend, sensing I was trying to make myself look manly in front of them both, asked me what my “move” was to get a blowjob in a movie theater. I told a story about pulling my cock out during a make-out session, pulling up the armrest between the girl and me, grabbing the back of her head and pushing her face towards my crotch. I boasted about how the girl would then do what came naturally, trying to sound cool, but neither James nor my girlfriend was buying it. They looked at each other and laughed at me. I suddenly felt like a third wheel hanging out with my girlfriend and my friend.

Eventually, James had to leave, and I showed him out. He asked for my girlfriend’s number, and without hesitation, I gave it to him, since I had assumed Amy was now his friend too. He winked at me and left, and when I told Amy I gave James her number, she smiled in a very mischievous way.

“Well that’s convenient,” she blushed. “I was just about to ask you for James’s number.”

After Telling Him How to Get a Girl to Suck Dick in a Movie Theater, Your Buddy Invited Your Girlfriend to the Movies

Later that night, as I was reading in bed, Amy was applying some cream on her freshly shaven and smooth legs when she received a text. It was from James. She began texting with an ear-to-ear smile on her face, and I leaned over enough to ‘eavesdrop’ on their texted conversation.

“Wanna go to a movie tomorrow?” The text read.

“Sure. Finish work at 6. Husband has to work late tho.” Amy replied.

“Wasn’t askin’ him.” He replied, making her giggle.

“What u wanna see?” she texted back.

“Don’t care” he replied. “I just wanna try his lame-ass move on u.”


James sent me a text later that read: “dude, your movie-move worked like a charm. Thanks, buddy”. I had assumed James picked up some girl after hanging out with my girlfriend and asked him to tell me all about it next time we met.

I encouraged my girlfriend to buy the kind of panties James was telling me about, as I wanted to try his move on Amy, but she wasn’t interested in wearing sexy underwear for me. It didn’t come up again until I saw a Victoria’s Secret bag in our closet. Looking inside, I saw pink panties and instantly got hard wondering when she would wear them for me. Days passed though, and I assumed she would be wearing them for Valentine’s Day, which was around the corner. The only snag was, I was working that night, so any romance would come in the early morning the next day.

I didn’t bring up the panties because I assumed Amy wanted to surprise me. When Valentine’s Day came up, it was business as usual between my girlfriend and me. Before I left for work, I asked what she had planned for the evening. She told me a friend was coming over. I was happy she wasn’t going to spend the romantic day alone, at least until I came home. Before I left, she had stepped out of the shower, and I got hard watching her put on the Victoria’s Secret panties out of the bag. I was glad my guess was correct – that she was saving them for a special day. She was giddy when she kissed me goodbye. Man, I couldn’t wait to get home and have her ‘surprise’ me with her sexy underwear. I was so going to use James’s move on her when I returned.

I tried to get in touch with James about what I had waiting for me when I came home, but his cell was off.

Cuckold Cleanup on Valentine's Day
For more pics of Kyle Dean and Stephanie Amato see “Hot Guys Fuck”.

Your Buddy Left a Gift For You Inside Your Girlfriend’s Pussy on Valentine’s Day

When I got home that morning, Amy was fast asleep on her side of the bed. The blanket on the other side of the bed was opened and worn in. I was rock hard when I crawled into bed with my girlfriend, but my dick was throbbing. I lifted the blanket up slowly, so not to wake Amy up, and saw that she was, indeed, wearing the pink panties. I ran my finger against it and swallowed hard when I realized they were wet and sticky with the same clear liquid that was dripping down my pillow. I noticed that when I saw Laryssa put those panties on earlier, they hugged her skin. Now the panties were stretched out, mostly to one side. My girlfriend was wearing wet panties. Why would she do that? It was like she was too exhausted to change them before falling asleep, but what could she have been doing in bed that would fatigue her?

Amy awoke at that very moment and smiled at me, a little groggy.

“Mmmm…Happy Valentines’ Day, sweetie,” She said, kissing me on the cheek. She smelled like she had an active night. Her hair was a little messy, like it had been pulled from behind.

“I wore these just for you” she teased, grabbing my hand and putting in on her panties. I started to pull my underwear down, but she stopped me and said she wanted to do something different, she wanted me to eat her out.

“James said it was something you would enjoy,” she said with a wink. I crawled under the covers and took in the view before me. My girlfriend’s pussy looked like the scene of the crime. It was still beautiful, but wet. Her pussy looked like it had been loosened up very recently with something thicker than her vibrator. Amy pulled the cover away from my head and started recording me eating her out with her cell. This was a first – we never even entertained the idea of making a sex tape. This Valentine’s day was surely going to be different. I was happy to see my girlfriend try to mix things up a little in the bedroom.

As I started to lap up my girlfriend’s pussy, she moved her cell closer to my face. I could see the screen when her grip faltered as she squirmed from tongue’s activity. I could see that she wasn’t just recording footage, but uploading it to James’s cell. Amy’s phone suddenly went off, and an incoming message came in, a response from James.

“Breakfast of champions, lol” his message read.

As I lapped away at my girlfriend’s rather salty-tasting pussy, a something caught my eye from my peripheral vision. It was a pair of boxer briefs bunched up between the sheets. I grabbed them to toss them on the floor, assuming static cling attached them to our bedsheets before noticing that they were blue boxer briefs. Tommy John boxer briefs. I then looked up at Amy, who was still holding up her phone at me. Her eyes met mine, and she smiled before typing something on her phone and hitting ‘send.’

I didn’t have to read the message to know what it said and who it was sent to. With Amy’s eyes locked on mine, this was a pivotal turning point in our relationship. I had two choices. Jump into the washroom and douse my mouth with mouthwash, or keep lapping.

Amy looked at me and smiled again mischievously. It was like she knew what I was going to do. Or should I say, what I wasn’t going to do.

I Ate My Buddy's Cum Out of My Girlfriend's Pussy on Valentine's Day
For more pics in this series see “Bi Empire Pictures“.