Pranked

I sat in the living room of my apartment, watching television. My phone rang, and I answered the call.

“Hi, Mike, it’s Greg,” my friend said.

“Hey, Greg. What’s up?” I replied.

“Not much. What’s going on with you?”

“I finished working, and I’m watching the news.”

I worked from home as a help desk tech for an MSP. When I graduated college, I applied and was hired. After six months of training, I started taking calls and helping clients with computer problems. The work was easy, and I could choose my hours, provided I handled several tickets daily.

“Do you have plans for tonight? A few friends are getting together at my place tonight. Are you up to a party?”

“I don’t have plans. What time?” I said.

“We’re getting together at seven. I have a refrigerator full of beer and will order pizza. See you later,” Greg said.

“Sounds good. See you soon.”

I hung up, tossed the phone on the couch, and headed to my bedroom. After removing my clothing, I showered. While standing in the spray, I thought about the get-together. I hadn’t seen my friends for a few weeks.

****

Greg and I became friends in high school. We met while trying out for the swim team. Both of us made the team and began hanging around together. A few other members became friends, and we formed a small group.

After high school, many of the group went to college out of state or joined the service. Greg, Mark, and I stayed home, attending a local school. When we turned twenty-one, we started going to bars to have a few drinks and meet girls. If one of us got lucky, we’d share the details of our conquest with each other.

The three of us were practical jokers and had fun pranking each other. One night I was at our local watering hole, talking with a girl I met there. While sitting at a table, talking with the chick, Greg came over and put his arm around my shoulders.

“What’s this? Are you cheating on me, sweetie?” Greg said. He kissed my cheek, causing me to jerk away.

I jumped out of my chair and said, “What the hell, asshole!”

Greg put his arm around my waist. “Oh, baby, I know how much you love my ass.”

The girl left, telling me she wasn’t into bi guys. Greg laughed and said, “How’s it going?”

“It was great until you showed up. I think I had a chance with the chick,” I said.

Mark came to the table with three beers, handing Greg and me one. “You don’t want anything to do with that girl.”

“How do you know?” I said.

“I took her out three times. She wanted to eat at expensive restaurants and never put out. Greg saved you a bunch of money,” Mark said.

I laughed. “You could have told me instead of going gay.”

Another time, Greg had hooked up with a girl at the bar. He took her to his car to make out while Mark and I devised a plan. We waited for a half hour, then got a bright flashlight from my car. We went to the parking lot, found Greg, and shined the light in the window. He had the girl’s shirt off and was feeling her breasts while she played with his cock. When the girl saw the light, she screamed and covered her chest. Mark and I banged on the car’s roof and left.

Greg returned to the bar later, gave us the finger, and ordered a drink. Mark and I laughed, telling him it was a joke.

“It’s okay. After I told her you two were assholes and I knew you, she calmed down and blew me. I’m taking her out again tomorrow night,” Greg said.

While we didn’t play practical jokes on one another often, we did when the opportunity arose.

During our senior year of college, we all met girls and formed relationships. Greg dated Kim. Mark went with Sarah, and I dated Gail. The six of us occasionally went out as a group, but we usually dated our girls alone.

When we graduated, Greg became an accountant and worked for a large firm. Mark didn’t like college and became a carpenter in his junior year. I went to work for the MSP and moved into an apartment.

Gail and I spent our nights at my place when we could. She and I enjoyed many hours of sex, often sleeping together. One night, after several hours of intense sex, we cuddled in bed. She asked me if I was seeing anyone else, and I assured her I wasn’t. When I asked her the same question, Gail said she hadn’t dated anyone since we got together.

I was considering asking her to move in with me, but things changed. Greg, Mark, and I went to the Starlight, a bar we hadn’t visited. When we walked in, I saw Gail sitting with another man.

I stopped my friends, asking them to stay hidden from her and her friend. As we watched, we saw Gail kissing the guy and rubbing his crotch while he had his hand under her skirt. Rather than making a scene, I walked out of the bar.

“That’s fucked up,” Greg said as we walked to the car.

Mark nodded. “Hell, yes, it is. Did you know Gail was cheating on you?”

“I didn’t have a clue. It’s a good thing I didn’t ask her to move in with me. I thought we were serious, but I guess not.”

“You should go back and confront her,” Greg said.

I shook my head. “What good would it do?”

“It would let Gail you know,” Mark said.

“Don’t worry. I intend to let the cheating bitch know.”

We went to another bar. Mark and Greg cut me off when I tried to drown my sorrows in booze. They took me home, made sure I got into my apartment, then left.

Gail came to my place two days later. When she walked in, it was all I could do to not lash out at her. We hugged and kissed as usual, then I offered her a drink. She sat on the couch, and I sat beside her. We chatted briefly about our day, sharing what we had done. After a few minutes, she put her arm around me, and we kissed.

I felt my stomach churn when I thought about Gail kissing the guy in the bar. It was all I could do to continue making out with her, but I soldiered on. As we kissed, I put my hand under her shirt and caressed her breasts. When I reached for the snap on her jeans, she helped me.

I unfastened her pants, then opened my shorts and exposed my cock. She stroked me, causing my dick to swell. I placed my hand on her head and guided her face to my crotch. Gail knelt on the couch, took my cock in her mouth, and sucked me while I put my hands in her pants and rubbed her pussy.

When we began having sex, Gail told me she didn’t mind sucking my cock, but didn’t like come in her mouth. I honored her request and always stopped when I felt my orgasm building, and we’d fuck. As she bobbed her head and sucked me, I decided to give her my cum.

I felt my cock swell, knew I was close, unloaded my cum into her mouth. Gail gagged and coughed, causing my spend to run out of her mouth. She jerked away, looked at me.

“Are you trying to make me sick?” Gail said.

“No, I’m not trying to make you sick, Gail. I wondered if you let other guys come in you mouth.”

Gail wiped her mouth. “What are you talking about?

“You told me you weren’t seeing anyone else.”

“I’m not.”

“Then who was the guy you made out with at the Starlight the other night? Greg, Mark, and I went there, and we saw you kissing a guy while he fingered you, and you rubbed his crotch.”

I watched the color drain from Gail’s face. She began babbling while pulling her shirt over her breasts.

“I can explain, Mike,” Gail said as she started crying. “He is a guy I work with, and things got out of hand when he took me for a drink.”

“Stop lying to me, Gail. I don’t believe you. You lied to me, and we’re finished. You can date anyone you want now.” I stood and fixed my shorts. “Just get the hell out of here and never contact me again.”

“I’m sorry, Mike. Please give me another chance. I’ll do whatever you ask to make it up to you.”

“Anything?”

“Yes. I’ll let you come in my mouth or fuck my ass if you want.”

“Well, if you’ll do anything. Leave!”

When Gail tried to hug me, I showed her the door. She pleaded with me, but I wouldn’t relent. After she left, I poured a drink and sat on the couch. It hurt, but I didn’t want a relationship with someone who would lie to me. While I was fond of Gail, I wasn’t in love with her. I would have understood if she had been honest and told me she dated others. I could have made a decision whether or not I wanted to continue.

I told them what I did the next time I got together with Greg and Mark. They laughed, telling me I was cruel.

It had been six months since I booted Gail, and I was ready to move on. Getting together with my friends was what I needed, even though I’d be a fifth wheel.

****

I chuckled as I finished my shower. It had been a while since I’d thought about Gail. I dried, shaved, and dressed for the evening. Since I knew we’d drink, and Greg wouldn’t let anyone drive if they did, I tossed a clean change of underwear and toiletries into a small bag.

I saw Mark and Kim’s cars in the driveway when I arrived at Greg’s house. I went to the door, knocked, and waited for someone to answer. Kim opened the door, letting me in. She led me to the family room, where I greeted Greg, Mark, and Sarah. A moment later, I heard the doorbell. Kim excused herself, left the room, and returned with a girl I didn’t know.

“Mike, I’d like you to meet my friend, Kelly. Kelly, this is Mike,” Kim said.

I extended my hand and shook hers. “Hi, Kelly. I’m pleased to meet you.”

Kelly smiled. “Likewise.”

I released Kelly’s hand and looked at her. She was tall, thin, and cute in her own way, with her shoulder-length hair pulled into a ponytail. We sat on the chairs and couches in the family room while Greg offered us drinks. Mark and I asked for a beer, and the girls asked for mixed drinks.

We visited with each other for a half hour, then the pizzas arrived. Greg gave us paper plates, and we ate. Greg put a move on, and we watched it while drinking. As the night wore on, Sarah and Mark started kissing. A few minutes later, Kim sat on Greg’s lap, and they made out.

Kelly looked at me, smiled, then moved to the couch, sitting beside me. She moved her head close to mine and whispered.

“I hate feeling left out. Don’t you?” Kelly said.

I nodded. Kelly leaned closer, put her hand on my cheek, and turned my head to hers. She pressed her mouth to mine, kissing me. When I felt her tongue against my lips, I parted them and accepted it. As we kissed, I ran my hand over her back, feeling her bra strap. She kept her mouth against mine and moved onto my lap.

Pulling her head back, Kelly said, “Too fast?”

“Not for me,” I replied.

“Good.” Kelly kissed me.

Kelly wasn’t the first girl I’d kissed or had sex with the first time we’d met. After what happened with Gail, I was ready for fun. The longer we made out, the more passionate we became. We stabbed our tongues together, and I continued rubbing her back. When I placed my other hand on her chest, she moaned.

Flexing my fingers, I massaged her small breast. She leaned against my hand, sucked my tongue, then we broke our kiss. When Kelly reached for her drink, we took a break. She moved off my legs, sitting beside me and straightening her skirt. I found it strange that Kelly wore a skirt and top when the other girls wore shorts. Glancing at her legs, I saw she also wore stockings or pantyhose.

Kelly noticed me and smiled. “I came straight from work. That’s why I’m dressed as I am.”

“I think you look great, Kelly. I like seeing a girl dressed as you are.” I sipped my beer. “I’m pushing things, aren’t I?”

Kelly shook her head. “No, not at all. It’s been a long time since I’ve been with a man who is so gentle and handsome. Don’t get me wrong, I don’t date many men.” She put her hand on my arm. “Kim told me about your ex-girlfriend. She said you might be ready to move on.”

I wondered how much Kelly knew. Glancing at the others, I saw they were busy making out and not paying attention to us.

“I am, Kelly.”

Kelly held her glass. “I’d like another drink.”

I went to the kitchen to make Kelly a drink and get a beer. When I returned, she stood, took her drink, and smiled.

“Thank you. Let’s find somewhere more private,” Kelly said.

I followed Kelly to one of the guest rooms, went in, and she closed the door. After sipping our drinks, she took mine and placed it on the nightstand with her glass. She wrapped her arms around me, and we kissed.

Kelly moved me to the bed and sat, pulling me next to her. We came together, kissing and running our hands over each other as she fell back. I followed and lay on my side beside her. As we kissed, I returned my hand to her chest and caressed her breast. She moaned when I slipped my hand under her top and felt her bare flesh.

I located the hasp of her front closure bra, unhooked it, and covered her breast. She squirmed as I toyed with her firm nipple.

Kelly broke our kiss. “They’re not very big.”

I cupped her small breast. “I think they’re perfect.”

We resumed kissing. I rubbed her breasts, moving between them. After working her top over her breasts, I kissed them. Kelly held my head, moaning as I flicked my tongue over her tiny nipples.

While I kissed her breasts, I moved my hand over Kelly’s side and to her hip. Rubbing her butt, I pulled her closer. She squirmed against me, running her fingers through my hair. When I started pulling her skirt up, she stopped me and sat up.

“Mike, we have to stop. I’m sorry.”

“What’s the matter? Did I do something wrong?”

Kelly shook her head. “No. You haven’t done anything wrong. Everything feels so right.”

“I think so. So, why did you stop me?”

Kelly pulled her top over her breasts and took my hands in hers. “This is hard, but I feel you deserve an explanation. Mike, your friends asked me to prank you. They told me you guys often did it to each other. Greg and Mike are playing a practical joke on you.”

“What? They asked you to make out with me and then stop cold?”

Kelly shook her head. “No. I was supposed to go further but can’t do it to you. You seem like a nice guy, and I can’t be that cruel. If I hadn’t stopped you, you would have discovered my secret, and it may have really pissed you off. I don’t want to cause trouble for you and your friends.

“When Greg and Mark told me what they wanted me to do, I agreed because they said you’d understand. I’m afraid you won’t. We should forget it and stop.”

“If that’s what you want. I would never ask someone to do something they didn’t want.”

Kelly nodded, then smiled. “It isn’t that I don’t want to, Mike. As I said, I’m afraid of causing problems. Things may be different under other circumstances, but it is what it is.”

I sat up, grabbed my beer, and drank it. Placing the can on the nightstand, I smiled.

“Will you tell me your secret?” I asked.

“Only if you can promise not to get mad at your friends or me.”

“I promise.”

Kelly took a drink of her cocktail. She looked at me and said, “Mike, not everything in life is as it appears.” Kelly shook her head. “I’m sorry, I can’t.”

“Can’t or won’t?”

“Are you sure?” I nodded. “Remember, you promised not to get mad. I want you to know I’ve really enjoyed the last few hours. I like kissing you and feeling you touch me.”

“I have enjoyed it too, Kelly.”

Kelly moved until she stood near me while I sat on the bed waiting. She took a deep breath, bit her lower lip, and closed her eyes. Running her hand down her legs, Kelly grabbed the hem of her skirt, slowly raising it. When she’d gathered her skirt at her waist, she opened her eyes and stared at me.

I lowered my gaze, stopping when I saw the bludge in her pantyhose. It took a moment for me to realize Kelly had male genitalia. I stared, took a breath, looked up, and saw tears run from her eyes. Kelly’s body shook as she waited for me to respond.

My mind raced as I remembered an incident from seven years ago. Mark, Greg, and I were eighteen and virgins. After a swim meet, we were alone in the shower and goofing around. We started playing grab-ass, and before we finished, we touched each other’s cocks. We never took it further, but I’ve wondered since then.

Before I said anything, I put my hands on her thighs and pulled her closer. I moved a hand to her inner thigh, ran it higher, and rubbed her cock and balls. Kelly gasped when I touched her.

Looking into Kelly’s eyes, I smiled. “I have to say that’s the biggest clit I’ve ever seen on a woman.”

“You’re not mad?” Kelly’s voice quivered.

I pulled Kelly onto the bed, kissed her, and rubbed her crotch. “Now, where were we?”

Chuckling, Kelly undid my belt, unbuttoned my pants, lowered my zipper, and extracted my cock. She wrapped her hand around my shaft, stroking me. I worked her pantyhose and panties down and fondled her dick.

As we rubbed each other’s cocks, we kissed. I broke out kiss and removed Kelly’s clothes while she removed mine. When we were naked, we looked at one another’s bodies. Kneeling beside me, Kelly leaned over and covered my cock with her mouth. She bobbed her head, taking me deep, then sat back.

“Yours is bigger than mine,” Kelly said, then chuckled.

I wrapped my fingers around her five-inch cock and stroked it. After a few minutes, Kelly took my cock into her mouth again. My thoughts were a blur as I relished the feeling of Kelly sucking my cock. While I had thought about having sex with a man, I never acted on it. Now I was lying with a woman with a cock, wondering what to do.

Running my hand over her body, I felt her softness. I covered her breast, massaging the small firm mound. As I played mental ping pong, I realized Kelly wasn’t a man. She was a woman with a dick. I didn’t know why she chose to be transexual or if it mattered. Feeling her caress my balls with my cock in her warm sucking mouth turned me on as much as I’d ever been. I ignored how we came to be where we were and made my decision.

I tugged at her until she lay on her side, pulled her close, and covered her dick with my mouth. Kelly moaned around my cock as I sucked hers and moved my hand on her breasts to remind me she was a woman. A woman with a cock, but a woman nonetheless.

The fact it didn’t bother me at all was surprising. For some unknown reason, having Kelly’s cock in my mouth seemed natural.

Kelly and I continued until I felt her come and shoot her cum into my mouth. I followed, filling her mouth with my semen. After recovering, I flipped around and kissed her. We wallowed on the bed, rubbing our naked bodies together.

“I must tell you I never expected what we did together. The plan was for me to reveal myself, then go out and have a laugh. Mike, I’m not laughing.” Kelly ran her hand over my chest. “Why did you do it?”

“Because I enjoy having sex with a sexy woman.”

“Even a woman with a penis?”

“Sure, as long as she isn’t bigger than me.”

Kelly chuckled and caressed my semi-hard cock. “I don’t think that’s a problem for you. You have the biggest cock I’ve seen.”

“Have you seen many?”

“No. You’re the third man I’ve been with.” Kelly chuckled. “You’re the first man to give me head. The other two wanted me to take care of them but wouldn’t touch me. I only went out with them once. I didn’t want to be with anyone who treated me as a freak.”

“Can I ask why you decided to become a transexual?”

“Sure. When I was younger, I never felt comfortable as a boy. I used to dress in my sister’s clothing and wonder what it would be like to be a girl. It wasn’t about sex but rather how I felt. When I turned eighteen, I moved away and began hormone therapy. After three years, I was a woman with a penis.”

“Have you considered surgery?”

“I thought about it but couldn’t afford it if I decided to have my penis removed. The only thing I had done was remove my Adam’s apple. I may have my boobs enlarged one day.”

Running my hand over her chest, I shook my head. “Your boobs are perfect the way they are.”

“Thanks, I’m glad you like my tiny tits. I guess we should dress and face the music.”

I put my hand on Kelly’s head. “I have a better idea.” I kissed her.

Kelly and I made out and touched each other. I played with her breasts and genitals while she stroked my cock. After a half hour, I moved between her legs and covered her cock with my mouth. Unlike our first encounter, I took my time and made love to her dick instead of just blowing her. As her cock swelled in my mouth, I realized there was nothing offputting about it. It was strange looking at a woman with her cock in my mouth.

I removed my mouth and took her small testicles in my mouth, rubbing them with my tongue. Kelly placed her hand on my head and moaned when I licked the length of her cock. Before moving up and kissing her, I swallowed semen for the second time. I wasn’t sure where things would go for Kelly and me, but if I had my way, it wouldn’t be the last time I sucked her cock and ate her cum.

Kelly and I kissed for a few minutes, then she moved lower and sucked my cock and balls. It took a while for me to come, but it didn’t deter Kelly. When she finished, we cuddled, kissed, and fell asleep in each other’s arms.

When I woke in the morning, Kelly’s head rested on my chest. I rubbed her back, moved lower, and felt her firm ass. She sighed and wiggled against me, then opened her eyes. We smiled at each other, then kissed.

“Good morning, sexy,” I said.

Kelly nodded. “Good morning. I didn’t expect to find you here this morning.”

I furrowed my brow. “Why?”

“I don’t know. I figured you’d sober up, realize what we did, and bolt.”

“Nope. I wasn’t so drunk that I didn’t know what we did together. Kelly, believe me when I say I enjoyed every moment. If you’re wondering, I’m not gay. I’ve never done anything serious with a man.” Kelly laughed when I told her what Mark, Greg, and I did in the locker room.

“So, what will you do when you see the others? Everyone except you knew about me.”

I kissed Kelly, rubbed her breasts, and said, “I’m going to thank them. I don’t know what they expected, but I’m sure it isn’t what happened.”

“Wow! You’re amazing, Mike. I have to thank you too. You’re the first man who made love to me. The first time we did it was fun, but the second time was special. I can’t explain how you made me feel.”

“Next time, I’ll try to up my game.”

“Are you saying you want to go out with me?”

“Of course. That is if you want to.”

“Oh, Mike, I’d love to go out with you.” Kelly hugged and kissed me.

“We should shower and get coffee. If nothing else, I have to take a leak.”

I got out of bed, took Kelly’s hand, and pulled her to her feet. When I headed for the door, she stopped me. “Don’t you think we should dress?”

“Why? We’re going across the hall and would have to undress.”

“I’m not sure I’m ready for anyone to see me, Mike.”

I put my hand between Kelly’s legs and massaged her genitals. “Why not? If you’ve got it, flaunt it.”

“What am I going to do with you?” Kelly said.

“You can wash my back.”

Kelly and I laughed as we left the room and went to the bathroom. I stood in front of the toilet, took a piss, and flushed. Kelly blushed when she sat on the toilet.

“I’m used to sitting because I use the ladies’ room.”

“That makes sense.”

Kelly and I showered, taking time to run our soapy hands over each other. When I washed her cock, she chuckled.

“This is the first time I showered with a guy since high school,” Kelly said.

“I don’t know about you, but I enjoyed it.”

Kelly nodded. “You have no idea how much I’ve enjoyed everything, Mike.”

We wrapped ourselves in towels, returned to the bedroom, and kissed. I excused myself, telling Kelly I was getting my bag. She nodded and asked me to get hers.

Kelly and I dressed, straightened the bedroom, and headed to the kitchen. When we entered, the rest of the group sat at the table, drinking coffee. No one said anything while I fixed two coffees and gave one to Kelly.

We shared uneasy glances with our friends when Kelly and I sat at the table. I grinned, and looked at Mark, then Greg.

“Thanks, guys.”

Greg nodded. “Are we okay?”

“I don’t know about the rest of you, but Kelly and I are great,” I said.

Mark shook his head. “We sat in the family room waiting for you to come in and rip us a new one.”

I put my hand on Kelly’s head, kissed her, and said, “Nope.”

After we ate breakfast, Kelly and I left. She followed me to my apartment, and we spent the weekend getting to know one another. By the time she left on Sunday night, we’d agreed to date. Kelly and I got together with our friends and enjoyed our time together. No one ever spoke of the night Greg and Mark tried to prank me for a few weeks. One night while the three of us sat in a bar, I told them some details of the night, but not everything.

A month after we met, I took her anal virginity. We were in bed, kissing and touching each other. When I pressed a finger against her anus, she wiggled. I continued touching her as she moaned.

“Are you going to fuck my ass?” Kelly asked.

“I’d love to if you’re good with it.”

“I don’t know if I am or not. I’ve never been fucked.” Kelly kissed me and stroked my cock. “I want to try.”

“We should wait until we have lube. I don’t want to hurt you, Kelly.”

Chuckling, Kelly climbed out of bed, grabbed her purse, and removed a bottle of lube. She crawled beside me and handed me the bottle.

“Here.”

“You planned it?” I said.

“I hoped you’d want to. I’ve fingered my ass and used a dildo, but I want a real cock.” She stroked me. “You’re bigger than my dildo, but I still want you.”

I kissed Kelly, put her legs on my shoulders, and smiled. Using my finger, I rubbed her anus, coating it with the slick lube. When I slipped my finger into her, she moaned and pushed back. After fingering her for a moment, I added a second digit, opening her.

“I’m ready, baby. I want your cock in my ass. Let me roll over,” Kelly said.

I shook my head, moved closer, and rubbed my cock against her anus. “I want to watch your beautiful face when we make love.”

Gripping my cock, I pressed the head against her slick asshole. When it slid in, Kelly’s eyes went wide, and she smiled. Rocking my hips, I pushed more of my shaft into her rectum.

When our bodies met, I paused. “Are you okay, Kelly?”

“It feels amazing, Mike. You can move.”

I withdrew my cock about halfway, then pressed in again. Kelly gripped my arms as I sped up, fucking her ass. After a few minutes, I supported myself with one arm and stroked her cock. She moaned, telling me to move faster.

While I screwed her, Kelly moaned and chanted. I felt my climax building, shoved into her bowels, and came. As my cum shot into her rectum, she came, spraying her stomach with semen. When I started to remove my cock from her ass, she stopped me, telling me to leave it in her. We remained connected until my dick softened and fell out.

“Wow! That was wonderful, Mike. I hope you enjoyed it because I want to do it again.”

I kissed Kelly. “You’ll have to give me time to recover, baby.”

When I asked if she wanted to fuck me, she shook her head. Kelly had no desire to fuck me or anyone else.

Kelly and I showered, taking turns washing each other. We talked about our first venture into anal sex, agreeing we both enjoyed it. While we ran our soapy hands over one another, we professed our love.

Three months later, Kelly moved in with me. We’ve been together for almost four years. Mark married Sarah, and Greg married Kim. Kelly and I stood up for both couples. When Kim became pregnant, Kelly and I talked about adopting a child. We haven’t done it yet, but who knows, maybe someday.

Greg, Mark and I never pranked each other again. We had more important things in our lives than practical jokes. I remember the first night with Kelly, realizing the joke was on my friends.