A Threesome Between Friends

When his dick stopped throbbing I was a little relieved. I had accomplished my goal of swallowing everything he had, but my knees were starting to get a little sore. I looked up to see still had that huge smile on his face. I tried to smile too, at least as best as I could with a humongous dick in my mouth. He started to go limp and slipped out of my mouth.

As I was about to get up his dick leaked one final drop of cum. I licked it off, making sure I finished the job.

"Damn! You really like my cum, huh?" Trent said.

"I guess so," I said.

"Did you enjoy my husband's cock?" Jessica asked me.

I turned around to face her. My dick was completely had and had slipped out of my thong.

"Nevermind," she said, "I can see that you did."

"Yeah, it was nice," I said. "Was it good for you?" I asked Trent.

"Oh yeah, you can blow me anytime!" He said.

"Well save it in your memory bank, because that was the one and only time," I said.

"Never say never," he said.

"Ok, you two had your fun. My pussy is soaked and I can see my best friend is ready to fuck it!" She said.

Trent said, "You two can get started. I need a drink of water and then I'll join you in bed. It won't take me too long to get ready to tap that ass!"

It took me a second to realize he was referring to my ass, but when my hole throbbed around the plug I was wearing, I got a little excited.

Trent left the room and I gave Jess a suggestive look. She nodded giving me the green light. I put my hand behind her head and pulled her into a deep kiss. My tongue entered her mouth and we were making out like teenagers again. It didn't matter that I was still wearing the underwear she got fucked in on her wedding night. All that mattered was that we were finally together, at least for one night, and I was going to enjoy every second of it.

We continued to kiss as I walked her backwards towards her bed. When we reached the foot of the bed she sat down and broke the kiss for a second to lie back. I was on top of her in an instant and my tongue was in her mouth again. My hard dick was still sticking out of the side of my thong and I reached down to take my panties off.

Jess broke the kiss again and said, "No, leave them on!"

This time she pulled my head down to hers and initiated the kiss. My hands got to work and I was massaging her breasts and her nipples. She was letting out muffled yelps as she was enjoying the sensations.

She looked at me again and said, "I'm so wet for you. I've been waiting for this my whole life!"

"Me too!" I said.

"Then what are you waiting for! Fuck your best friend!" She said.

I reached down to position myself and entered her slowly. We both moaned as we had reached the moment of truth. Before going any further I gave her a look again to ask for permission.

"Yes!" She replied. "Come on! Fuck me! I need your cock!"

"Whoa," I thought to myself. I had never heard those words from a woman before and I never expected to hear them from my best friend.

I didn't waste any more time and I plunged all the way inside her in one smooth stroke.

"Oh My God!" She screamed. "You're so big!"

I figured she was just playing along since Trent was much bigger than me. It didn't mean that I couldn't play along too.

"You like that, huh?" I asked. "You like the way I fill your tight little pussy?"

"Oh yeah, you feel amazing. Now shut up and fuck me!" She said.

The time for talk was over. I pulled back leaving just my tip inside of her and a thrusted in hard. She yelped and I caught her mouth to start kissing her again while I fucked her.

I wanted this to last so after a few deep thrusts I slowed down. I don't know how long we were going at it, but I felt some pressure on the mattress. I was too focused on fucking and kissing that I didn't look back. Of course it was Trent.

A few seconds later I felt both of his hands on my butt cheeks. He pulled down my thong and as he started to spread my cheeks I froze. I knew he was going to fuck me at some point tonight, but was he going to do it at the same time I was fucking his wife?

Trent said, "Just relax and keep pleasing my wife. Pretend I'm not even here."

That was easy for him to say. I've never had anyone touch my ass like that before and certainly not during sex. Jess and Trent must have discussed this at some point because she scooted up a bit. Instinctively I moved with her and now I was fucking her with my back bent and my ass sticking up higher. I guess he was going to fuck me now.

I felt him grab the butt plug that had been lodged inside of me for over an hour now and pull it out. I tried to relax like he said and braced myself. He spread my cheeks even wider and instead of his dick entering me, I was surprised to feel his tongue. He wasn't going to fuck me, he was eating my ass.

This was another totally new sensation. We had talked about sex and blowjobs, but this never came up. I'm guessing Jess put him up to this, because I couldn't see him volunteering for it. I didn't care either way. His tongue felt wonderful and I was relaxed enough that I picked up my pace. Jessica groaned in delight as she was getting close to another orgasm.

"Oooh yeah, soooo gooood!" She said. "I'm so close. Come on! Do it!"

I thought she was talking to me and I started fucking her harder. It turns out she wasn't talking to me and Trent stopped licking my hole. I felt something hard rest against my entrance and figured this was it. I braced myself as a large object entered me. It was definitely bigger than the plug I had in earlier. It wasn't moving so I wasn't positive what it was. Trent's hands left my cheeks and he slid up next to us.

"How do you like that? That is a dildo that's a replica of my cock! I had it made for Jess for when I go away on business. Now that you know you can take my cock you don't have to be worried about it!" He said.

Jessica said to Trent, "That's great Baby, but we're kinda in the middle of something here!"

"By all means, enjoy yourselves. I'm ready to tap that ass as soon as you're done! I'm all boned up for you!" He said.

Hearing those words made my dick throb. I started to jackhammer her and she was going wild. A few thrusts later she screamed out.

"I'm cummmmming!" She yelled.

Her orgasm made her pussy squeeze my dick. I couldn't hold out any longer and I unloaded inside of her. Not wanting it to end I continued with short thrusts as we made out. Finally my dick went limp enough that it slipped out of her. I kept kissing her as I lied on top of her.

"That was hot watching you two cum together!" Trent said. "Now it's my turn! Are you ready?"

"I guess sooooo," I was interrupted as he quickly pulled me onto my knees and pulled his penis replica from my ass.

Jess scooted up and was now sitting against the headboard.

She looked into my eyes and said, "Just relax and enjoy yourself. If something doesn't feel right, just tell him. If something feels amazing, definitely tell him!"

I saw her look past me and nodded. This was the signal for Trent to start fucking me. I must have made a face, because she grabbed my face and started kissing me. I melted into her kiss as his huge dick pressed against me. Between the plug and the dildo I was loose enough for him to pop inside. I yelped into Jessica's mouth and she just kept kissing me.

Trent stopped and asked, "Okay?"

Jess let go so I could respond, "Slowly please," I said.

He listened and entered me slowly. Surprisingly it didn't hurt as much as I thought it would. He was definitely stretching my asshole, but I was staring into my best friend's eyes and taking it. There must be a reason guys like anal sex and I was about to find out.

Trent continued to push into me and he hit a spot that gave me chills up and down my body. I moaned in pleasure.

"I knew you'd like this!" She said.

"What was that?" I asked.

"That's your special spot, honey. Trent is going to pay special attention to it and you're gonna cum harder than you ever have before!" She said.

"Mmmmm" I moaned again.

"Is that what you want?" He asked me.

"Yes please," I replied.

"Deal, but first I'm gonna pound the hell out of you!" He said.

In an instant he thrust his huge cock all the way inside of me and I felt his balls bump against mine. Then he pulled back to his tip and thrust into me all the way just like I had done to his wife. It was certainly different being on the other end of it.

His hands were on my hips and he was drilling me doggy style. Each time he would go in and out he would press my spot ever so slightly. I couldn't tell if he was doing it on purpose to tease me, or if he didn't have any control over it. I was doing my best to be an active partner thrusting my hips back at him, but he was fucking me like an animal and I loved it so much that I decided to just relax and take it. I never considered anal sex and now I'm so glad I agreed to it.

I could feel his pace slowing and he must have been getting tired. That seemed to be better for me, because the slower pumps were triggering my spot. I had been semi hard the entire time he was fucking me, but all of a sudden my dick sprang up and I felt like I was going to explode. I picked up a hand to touch it, and Jessica slapped it away.

"No, no, no, cum from his dick, not from your hand!" She said.

"Yeah, let me take you there!" He said, "Are you close? Because I am!"

"I think so," I replied, "My dick feels like it's gonna blow, but there's something missing"

"Hold on," he said.

He pulled back and thrust in hard and stopped about halfway. Then he pressed against my magical spot and I yelped.

"Yes, yes, right there. Fuck me right there!" I implored.

He listened and started to hit me in the same spot with short but forceful jabs. My tingles were back and my whole body was covered in goosebumps. I looked up at Jessica and she had a huge smile on her face.

A few more pumps and I screamed out, "Oh My God! I'm cumming!"

My body shook and my dick turned into a fire hose, blasting all over their sheets. My ass clenched around his dick and I started to fuck him back as I came. The pressure was too much for him and exploded inside me.

"Here it is! Take my load you little bitch! I'm gonna fill you up so much!" He screamed.

He continued to fuck me hard through his orgasm. I could definitely feel him cumming. It was a warm sensation with constant spurts. I assumed he wouldn't have as much in the tank after how much he came from the blowjob, but that wasn't the case.

When he finally slipped out of me I rolled over on to the bed, right in the wet spot I had made. I didn't mind though, it was a fitting end to a night of firsts. Trent rolled over next to me and Jessica cuddled next to me.

I looked at Trent and said, "Little bitch, huh?"

"Sorry about that. I guess I got caught up in the moment," he said.

"That's fine, as long as you don't ever call my best friend that!" I said.

"Of course not!" He said.

Jessica continued to snuggle next to me and said, "This was nice, right?"

"It was wonderful!" I said.

"Would you like to sleep in here with us tonight?" She asked.

"Sure, if you want me to," I said, "But can I make a few requests."

"Of course," she said.

"First I'd like to take these stockings off, they're kinda hot," I said.

"Of course, but you have to sleep in your bra and panties," she said.

"My bra and panties? Are they mine now?" I said, laughing.

"Sure, you should keep a memento from tonight," she said.

"I was joking, but we can talk about that later," I said.

"What else?" She asked.

"Can I help you change the sheets?" I asked.

"Of course, that's actually a good idea," she said. "Is that it?"

"Last thing, can I go clean up quickly? Your husband shot so much cum in me I don't want to be leaking all night," I said.

"I'll take this one," Trent said, "Sure you can go clean up, but as for your ass, we think it would be pretty hot if you wear the butt plug to bed and keep my gift inside of you overnight."

"We?" I asked, "You both want me to sleep with your sperm swimming around inside me?"

"Yeah, you know, seal the deal!" Jess said, laughing.

"Very funny!" I said, sarcastically.

"I thought so," she said, still laughing.

"Fine, bra, panties, and plug, but I get to take off this wig and makeup. Deal?" I said.

"Deal. I'll go get the sheets and you do whatever you need to do in the bathroom," she said.

Trent leaned over and picked up the smaller butt plug.

"And don't forget your plug. Do you need help putting it in?" He asked, winking.

I grabbed it from him and said, "I think I can handle it."

As I walked to the bathroom I could feel my ass starting to leak already. I closed the doors and wanting to keep my promise I walked towards the tub. I put my foot on the ledge and slid the butt plug inside my asshole. It went in easily and my hole gobbled it up, tightening around the wider tip at the end.

I looked in the mirror and after all the kissing, blowing and fucking, I still looked a bit feminine. It was fun to do this one time tonight, but I don't think I'd find myself dressed up as a girl again. I unclipped my stockings from the garter belt and got a brief chill as I slid the nylon off my legs.

I sat at Jessica's makeup table and found some makeup removal wipes. I took off my wig and wiped my face as best as I could. I walked back to the full length mirror and now I looked like a guy in a bra and panties.

Back in the bedroom Jessica was waiting for me. She was wearing a short black nightie that showed off her breasts and barely covered the black boyshorts she was wearing. I helped her change the sheets. Trent walked in a few minutes later and we all got in bed with me in between them. We were all pretty exhausted and fell asleep pretty quickly.

THE NEXT DAY

I woke up the next morning and it took me a minute to realize where I was. There was an unusual feeling on my shoulders and in between my butt cheeks. I was also being spooned and there was something hard pressed against me.

As I opened my eyes and saw my bra strap, last night's events came back to me. I was still in a bra and panties, and the person spooning me must be Trent. He had morning wood and it was pressed against me. I tried to move away from him, but he grabbed me tighter.

"Come on, we had such a great time with your best friend last night, but I didn't get to fool around with you," he said.

"Um Trent, it's me, not Jessica," I said.

"Oops, I'm so used to waking up next to her. I felt your ass rubbing up against my dick all night and was dreaming of her," he said.

"Well it's still me," I said.

I felt him turn for a second and he said, "Jess isn't here and I've got this raging hardon that you gave me."

"I'm not responsible for what happens in my sleep!" I said.

"Come on, didn't last night feel good?" He asked.

"Yeah, but it doesn't mean I want to do it again. Plus we both agreed were not into dudes. With no wig and no makeup I'm just a guy in lingerie right now," I said.

"I'm ok with it if you are," he said, "I need to take care of this erection or I'm gonna be miserable all day."

"You want me to blow you so you'll feel better," I asked.

"Actually, do you still have the plug in?" He asked.

"Yeah," I said.

"So you're all stretched out and lubed for me," he said.

"What?" I said shocked.

He grabbed my chin and kissed me. I had blown him and let him fuck me, but this was the first time we kissed. I'm not gonna lie, he was a great kisser. I melted into the kiss before I remembered I was kissing a guy.

"Dude, what the hell?" I asked.

"You didn't like it?" He asked.

"Yes, I mean no, I don't know," I said.

He reached down to the front of my thong and felt that I was hard.

"Your dick certainly liked it," he said.

"It's just morning wood, like yours," I said.

"So you need to cum too, let me make you cum like last night. It will be helping both of us out," he said.

"I don't know," I said.

He rolled me onto my back and got on top of me, kissing me again. We made out for a little bit before he stopped.

"This is nice and all, but it still doesn't feel right," he said.

He reached over into the nightstand and pulled out a tube of Jessica's lipstick.

"Here, put this on. It will make you feel girly and I love kissing bright red lips!" He said.

"Fine, but this is the last time," I said.

"I promise. Just lie back and let me do all the work. I'll make you feel so good again," he said.

I was defeated, but also a little excited to feel an anally induced orgasm again. I opened the lipstick and did my best to apply it.

He stopped me and said, "Perfect."

He pecked my newly painted lips and reached down to pull off my thong. I spread my legs as he got in between them. He pulled out my plug and I gasped at the sudden feeling of emptiness. He lifted up my hips and put a pillow under my back. He scooted up towards my face and started to kiss me. As we kissed he entered me slowly until his pelvis pressed against mine.

Between getting fucked last night and wearing the plug all night I wasn't uncomfortable at all. His dick felt really good and was just going to lie back and enjoy it. We kissed and he fucked me ever so gently. It was different from last night, just gradually in and out as we moaned into each other's mouths.

I was getting those shivers again and I knew I was close. Trent must have been close too because he picked up the pace. We were both startled as the door opened and Jessica walked in.

"I can't believe you're fucking without me!" Jessica screamed.

Before I could answer my body convulsed.

"Holy shit! I'm cumming!" I screamed as he gave me a massive orgasm.

As I coated both of our stomachs with my semen, my ass grasped his big cock and squeezed him to the point of no return.

"Me too! Your ass is amazing!" He said as he came inside me again.

Trent gave me one last peck on my lips and rolled off me. We were both breathing heavily.

"I thought we agreed last night would be it, but I guess you two couldn't help yourselves!" She said in a stern voice.

We knew she wasn't really mad, but we played along.

"I'm sorry Jess. I didn't mean to fuck your husband without you here," I said, "It kinda just happened."

"Yeah Jess," Trent said, "I'm sorry I fucked your best friend again. That ass was just so tight and inviting!"

"From the look of my best friend's bright red lips and the sounds you two were making, I guess you want to keep playing," she said.

"I'm game if you two are, but let's agree that today is it, at least for this trip, I don't know how much more my tight little butt can take!" I said.

"Oh don't worry, BFF of mine, since my husband took it upon himself to fuck my best friend again without my permission, I'm in charge for the rest of the day. Your cute little butt is safe for the rest of this trip," she said with a smirk on her face.

"What does that mean?!" Trent said, surprisingly.

"It means that you get to wear the lingerie this time. You're gonna suck my BFF to complete hardness and then he's gonna fuck me in the ass while I ride your cock!" She said.

"But Jess...!" He complained.

"No butts! Except mine! You took my best friend's anal virginity, so now he's gonna take mine! I've always been curious how double penetration feels, so we can actually have our threesome with both of you inside of me at the same time!" She said.

"But why the lingerie?" He asked.

"I had so much fun dressing him up and it seems you should dress the part for your first blowjob. Maybe you'll even get worked up enough that you'll beg him to take your ass too!" She said.

"Fine, I'll let you dress me up, but nothing is going in my ass! I'm not into dudes!" He said.

"Yeah, that's what I said, remember. Then you made me cum harder than I've ever had, twice!" I said.