A Threesome Between Friends

Author's Note: I was watching an old Seinfeld episode and it gave me this idea (with a sexy twist of course!) I'm trying to do something a little different here. It's hard to come up with new ideas since I'm not really into forced stuff or magical transformations. There aren't any life changing moments, just some lingerie and tons of sex between friends. Hope this story gets you there!

(Normal conditions apply, there is no risk of unwanted pregnancy or illness and our heroes are always ready to perform!)

A THREESOME BETWEEN FRIENDS

"There's something we'd like to ask you," Jessica said.

"Okay..." I replied curiously.

She hesitated and Trent said, "Just tell him, we're all friends here."

"I believe the term is Menage-a-Trois," Jessica said.

My jaw dropped and I said, "A threesome? With me? You guys want to have a threesome with me?"

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Jessica and I have been best friends since we were kids. Her family moved in next door when we were four years old. We went to school together and hung out all the time. She was a total hottie and I wasn't too shabby either.

During our senior year of high school we drank a little too much on her couch and we kissed for the first time. I went for a boob squeeze and she kissed me again as I felt her up. We made out for a bit until she broke the kiss and said she was tired. I went home with blue balls. I was totally in love with her, but I also didn't want to ruin our lifelong friendship.

When I woke up the next day I was curious what would happen. I decided that I wasn't going to say anything and let her bring it up. To my disappointment she didn't say anything. She texted me that she was ready to go to school and I drove her like I always did. I am definitely not a shy guy, but this was different. I couldn't open myself up to being hurt, and I didn't want to lose her. If she wanted to forget last night, I would have to forget it too.

We ended up going to separate colleges and she met the new love of her life, Trent. I was happy for her and was even a groomsman at their wedding. Once they got settled and bought a house they invited me to visit. Trent was a nice enough guy and he treated Jessica really well, which was the most important thing.

They had a nice home and a nice guest room so I wouldn't have to spend money on a hotel. We had just gotten back to the house after a nice meal. We had two bottles of wine between the three of us and Jessica had just popped a third. Halfway through the bottle I watched Jessica take a deep breath.

"There's something we'd like to ask you," Jessica said.

"Okay..." I replied curiously.

She hesitated and Trent said, "Just tell him, we're all friends here."

"I believe the term is Menage-a-Trois," Jessica said.

My jaw dropped and I said, "A threesome? With me? You guys want to have a threesome with me?"

"Yeah, if you're into it of course," He said and rubbed my thigh.

I jumped at his touch and said, "Ummm."

Jessica started to rub my other thigh and said, "Come on, I know you've been dying to fuck me!"

"Whoa!" I said.

"Remember that night we made out and I let you get to second base?" She asked.

"Of course, it was one of the best nights of my life," I said.

"So how come you basically ignored me the next day?" She asked.

"I was waiting for you to say something. I thought maybe you weren't interested," I said.

"You're the guy, you were supposed to make the move," she said, "I was totally in love with you!"

"And I was in love with you too," I said.

"Looks like your miscommunication worked out in my favor!" Trent said, laughing.

"Well, what do you think?" She asked me.

"What exactly are you talking about?" I asked.

"Like I said, a Menage, a Three-way, do we have to spell it out for you?" She asked, giggling.

I almost forgot their hands were on my thighs until their rubbing increased.

I said, "But I'm not into dudes." It came out in a high pitched voice like I was going through puberty.

"Aww you don't have to be nervous," she said.

"Yeah, I'm not into dudes either," he said.

Getting my normal voice back I said, "So what the fuck are you talking about?"

"Trent has been bugging me about a threesome since we got together. There's no way I will let him fuck another girl and being with one doesn't interest me either. I finally caved and said we could have one as our first anniversary present as long as if it was with you," she said.

"But we both just said we weren't into dudes," I said to him.

"Jess is a whiz with makeup," he said.

"You want me to dress up for you? As a girl?" I asked.

Jessica's hand moved towards my crotch and could feel that I was hard.

"Oooh, looks like somebody is into the idea," she said.

"I don't know, it's probably just a combination of the alcohol and that you've been rubbing my legs," I said.

"Come on, think of how hot it will be. You'll finally get to fuck me and I'll give you one of my amazing blowjobs," she said.

"But then I would have to..." I hesitated.

"Yeah, if Trent is letting you fulfill your fantasy and be with his wife, wouldn't it make sense that you repay the favor?" She asked.

"I've never done anything like that before. You really want me to blow you and then let you fuck me in the ass?" I asked Trent.

"I can think of nothing hotter than being with my smoking hot wife and her best friend," he said.

"And I'll make you hot too! I've always wanted a girl best friend. Come on, it'll be one night and I guarantee you'll have the time of your life!" She said.

"Guaranteed?" I asked.

"How can it not be? You'll finally get to be inside my tight little pussy and Trent's big dick is gonna feel amazing in your ass. You're gonna cum so many times tonight!" She said.

"And I'm looking forward to watching my wife get fucked, because that means I can finally fuck a hot chick in the ass! Your BFF is kinky, but she won't give up the butt," he said.

"That's not happening. You're way too big for my cute little ass. You fill my pussy up just right! That's good enough for me!" She said.

"Jeeze Jess, I've never heard you talk like this," I said, "And wait, if he won't fit in your butt, what makes you think he'll fit in mine?"

"Don't worry, we'll get you nice and ready," he said, "And I'll add a cherry on top, if at any point you don't like it, I'll stop. Deal?"

I hesitated and looked Jessica in the eyes. She gave me a suggestive look and licked her lips. I was torn. I really wanted to be with her even if it was only for one night, but I was petrified about letting Trent fuck me. I never even thought about being with a guy. He did say he would stop though.

I caved, "Deal!"

"Awesome, I'm so excited!" She said.

"Me too!" He said.

"Me three!" I said, playing along.

Jessica grabbed my hand, "Come on cutie, let's go get you ready!"

She led me into her bedroom. My eyes immediately went to their King Size bed and started to think about what would be happening on there in a little while.

"Excited?" She asked me.

"I think so," I said, reluctantly.

She looked down to see my hardon showing through my pants.

"Your dick certainly thinks so!" She said. "I think I need to take care of that first!"

"What about Trent?" I asked, nervously.

"Don't worry, you can blow him later," she said, giggling.

"That's not what I meant..." I began to say.

As I was talking she had pulled down my zipper and pulled down my pants and boxers. My rock hard dick sprang out and was staring right at my best friend. I was standing at the foot of her bed and she dropped to her knees, basically swallowing my cock.

"Ahhhh," I moaned.

As she took me all the way in her mouth she looked up at me and winked. I had a huge smile on my face. One of the hottest girls I had ever seen, who happened to be my best friend, was giving me a blowjob.

I had my share of blowjobs, but five seconds in, I could already tell Jessica's was going to be the best one ever. She had just the correct amount of suction and the way she was using her tongue felt awesome.

I had a feeling I wasn't going to last long, so I tried to relax myself to delay my orgasm. Jessica had other ideas. She started to bob her head and reached down to cradle my balls. Then I felt her hand move lower and go in between my butt cheeks. I was so into her blowjob that I didn't realize what was going on.

I jumped when she shoved her finger up my ass. My reaction didn't faze her and she continued to suck me as she played with my hole. Her finger was the first thing that had been up there, but wouldn't be the last after tonight.

A second finger followed and I could feel myself start to loosen up. My whole body was covered in goosebumps and I was about to explode. This all happened so fast and I wanted to do the right think and let her know when I was gonna cum, just in case she didn't want me to shoot in her mouth.

"Jess, I....." I said.

As I spoke she yanked her fingers out of my ass. I was so surprised that I couldn't continue to tell her what was about to happen.

I heard some rustling and I could tell she was reaching for something as she took me really deep in her mouth. Quickly her hand was in between my cheeks again and I felt something larger than a finger against my asshole. She pressed the object inside me hard and that me over the edge.

"I'm cummmmmmming!" I screamed as I exploded in her mouth.

She continued to suck me through my orgasm and my asshole was squeezing the foreign object she had put inside of me. It was definitely the best orgasm I've ever had.

When I finished shooting, she stood up and kissed me. She had swallowed my entire load, but I could still taste a little bit of myself.

She broke the kiss and asked, "How was that?"

"Fucking awesome!" I said, "But what did you put in me?"

"Guess," she said.

"Probably some type of butt plug or vibrator," I said.

"Ding, ding, ding," she said, "We told you we'd get you ready for Trent's dick. The plug isn't nearly as big, but it will get you started. I'll give you a larger one before the main event."

I was speechless.

"You're still ok with this, right?" She asked.

"Yeah, I mean after than amazing blowjob, how could I not be," I said.

"Cool, now strip the rest of your clothes off, I need to make you hairless," she said.

"You're gonna shave my whole body?" I asked.

"Yeah, hot chicks don't have any hair below their eyebrows," she said.

"I guess you're right," I said.

I took off the rest of my clothes and I followed her into her bathroom. I stood in front of the mirror as she looked me up and down.

"Somebody is a bit overdressed," I said, suggestively.

"I guess I am," she said, "Is there something you'd like me to do?"

"I was thinking I should see what I'm working with, you know for later," I said, smiling.

"You want me to take off my clothes now?" She asked, already knowing the answer.

"Yes, please," I said.

"Why didn't you just ask?" She said as she stripped down to her bra and panties.

She was wearing a matching Black Bra and Thong with her D cups threatening to spill out. If it's possible, she was even hotter than I remember. I looked her up and down as my dick started to stir again.

"Damn Girl!" I said loudly.

"You like?" She asked.

"You are the most beautiful woman I have ever seen!" I said as I walked towards her.

I wrapped my arms around her and she thought I was going in for a hug. She started to hug me back as she realized what I was really doing. I had taken a hold of her bra clasp and was unhooking it. We released each other's grip and her bra full to the floor, exposing her magnificent breasts. My hands went right for them and I felt her nipples harden.

She yelped and said, "Whoa, take it easy tiger!"

"I'm just making up for lost time! If you remember last time I got to touch them it was through your shirt and bra. I've always regretted not feeling them for real," I said.

"I guess its ok," she said as she moaned.

I continued to play with her tits as I slowly walked her towards her bathtub. As we reached the tub I let go of her left breast and took her nipple in my mouth. She gasped in pleasure as I sucked one nipple and rubbed the other. I switched to the other one for a bit and then began to kiss down her body.

When I reached the waistband of her panties I kissed her crotch through the material before pulling her thong down to her ankles.

"Sit down," I said.

"What?" She asked.

"Sit down please," I said.

She sat on the edge of her tub and I dropped to my knees. I spread her knees and lowered my head. Her scent was intoxicating. She had a beautiful pussy that was completely shaved.

As I inched closer she said, "Wait, what about Trent?"

"He gets to play with you all the time. It's my turn to pleasure your, what did you call it? Oh yeah, tight little pussy!" I said.

I kissed her right in the middle and she was already wet.

"Looks like you're enjoying this already!" I said.

"Mmmmm," she moaned as I started to go down on her.

I was always told I gave great head and my BFF was about to find out. I started by kissing her around the edges and teasing her. I was intentionally neglecting her clit and I could tell she was aching to be touched there. I licked her up and down for a little while and started to tease her with my fingers. I kept one just at the outside and applied a little pressure, but didn't go inside her.

I stopped for a second and asked, "Feeling good?"

"Yeah," she answered out of breath, "But can you please stop messing with me? I need to cum so badly!"

"Oh, that's what you want?" I said, teasing her. "All you had to do was ask!"

I lowered my head and gave her clit a long lick as I pressed a finger inside of her.

"YES!" She screamed. "Oh Yes! Right there!"

I continued working her clit and fingering her. She didn't last much longer after that. I felt her whole body start to tremble and she exploded all over my face with a loud scream. There's no way Trent didn't hear her, and part of me hoped he did.

I stood up and she kissed me deeply, tasting her juices from my face.

"Thank you! That was wonderful!" She said.

She looked down to see I was hard again.

"Looks like you enjoyed that too! But let's get you nice and smooth and dressed so we can invite Trent to join us.

She left the bathroom for a second and came back wearing a tiny pink silk robe. Her beautiful breasts and pussy were exposed and I assumed she hadn't tied shut on purpose.

She reached into her drawer and pulled out a can of shaving cream and a pink razor. I won't bore you with the details, but ten minutes later I was completely smooth. Next she applied some makeup and gave me a blonde wig.

Jessica led me to her walk in closet that was big enough to have a dressing area. On the table was a pile of white satin and lace.

"Is that for me?" I asked.

"Yeah, it's the lingerie I wore on my wedding night. I figured a virgin should have her first time in it," she said.

"You're the boss," I said.

Soon I was wearing a white bra, thong, garter belt and stockings. The material felt wonderful on my newly hairless body. I wondered why girls didn't wear stuff like this all the time.

The only blemish in my look was my raging hardon in my panties. I was already turned on knowing I was about to fuck Jessica for the first time, and wearing her bridal lingerie set me over the top.

She noticed lump in my thong and said, "Looks like someone is excited!"

"More than you know!" I said.

She slipped her robe off her shoulders and took my hand. She wouldn't be needing clothes for what was about to happen tonight, and I was only dressed the way I was to play the part.

She opened the doors to the bedroom and Trent was standing at the foot of the bed. He was completely naked with his massive dick sticking straight out. His hands were on his hips like he was Superman.

"Holy shit!" I said, noticing the size of his dick.

"Nice, right," Jessica said, knowing exactly what I was reacting to, "Your BFF did well for herself, huh?"

"Well I've really only seen mine, and his is definitely bigger!" I said.

Trent said, "Since it sounds like you two got started without me, why don't you come over here and get yourself acquainted with it!"

I gave Jess a look almost as if to ask her permission.

"It's ok," she said, "He won't bite."

"Yeah, just relax and take your time. Jess really did make you into a hottie! Just follow your instincts and act like her best girlfriend would," he said.

"And after you swallow his load, you get to fuck me!" Jess said excitedly.

I took a deep breath and said, "Okay."

I started to walk towards Trent. He was only a few feet away, but it seemed like it took forever to reach him. He was taller than me, so when I was finally standing in front of him, I had to look up to see his eyes. He had a huge smile on his face. As a reflex I smiled back with my bright red lipstick coated lips and for some reason winked at him. He put his hand on the top of my head and I took the hint and dropped to my knees.

My mind started to spin and a bunch of thoughts ran through my head. For the first time in my life I was face to face with a dick. Not just any dick, a massive one that would soon be in my mouth and later be in my ass. I was wearing my best friend's bridal lingerie, and I was about to have the time of my life.

I put my hands on Trent's thighs and a drop of precum leaked out from the tip of his dick. I stuck out my tongue and licked it off without thinking about it.

"Just like that," I heard Jess say from behind me.

Her words were encouraging enough so I opened my mouth and took his tip inside. I wasn't brave enough to take more yet, so I sucked on his head for a bit and swirled my tongue around it. This seemed to be working because he was moaning.

"Mmmm, so good!" He said. "Why don't you try to take some more?"

I listened and took a few more inches into my mouth. He really was huge and my lips were stretched as far as they could go. I continued to use my tongue as I worked on the next section of his dick and he continued to moan.

"There you go!" Jess said, "Now take as much as you can and suck my husband's cock!"

I started to take more of him and he put his hand on the back of my head. The combination of me swallowing his dick and his pressure on my head finally got to be too much. I had taken him as far as I could and I let out my own groan. Fortunately he realized what my sound meant and he let go.

I proceeded to give him the best blowjob I could. I was bobbing my head fast and essentially jerking him off with my mouth. My tongue was doing it's best to keep up too. I could tell he was enjoying it and Jess kept shouting words of encouragement. She would tell me later that she had been fingering herself the whole time I was blowing her husband and had an orgasm at the same time he did.

I had no idea how long I was on my knees giving my first blowjob, but I did know when it was about to end. Trent's dick swelled and my mouth was as stretched as it could be.

"I'm cummmming!" He screamed.

I wasn't exactly sure what to do, so I stopped bobbing my head and sucked him like a lollipop. Jess had mentioned swallowing his load, and to tell the truth I was kind of curious what it would be like.

His first shot blasted across my tongue. It tasted a little salty like everyone says, but it was a little sweet too. I gulped it down as he continued to fire in my mouth. He was giving me a huge load, definitely more than I have ever cum. I tried my best to keep him deep so it would be easier to swallow it all. It was almost like a challenge and I didn't want to let them down.