My girlfriend Lena and I were always into crazy, wild and spontaneous things. Always trying to one-up each other, we would create elaborate practical jokes on each other and always have a good laugh about it. It has been one of the strengths of our relationship… but sometimes the joke can go too far and take on a completely new meaning. That happened recently.
Now, Lena and I were not very shy about our sexuality. Both of us had experienced how the other half lived, but after we became a couple that seemed to taper off for both of us. It was, however, the occasional topic of conversation and every once in a while was the focus of a private joke between us.
We had been invited and were planning to attend a Halloween party with some friends of ours. The costume party allowed us to go big when it came to our characters. We had attended parties like this in the past; dressing as superheroes, cops, doctors and nurses… we didn’t find a costume we didn’t like. So, as we were thinking of what to portray this time around, Lena came up with the idea that we change identity. She would go as a man and me as a woman but also dressed in costume. I loved the idea especially since there was always prize money for the best costume.
So we took to the internet and started looking for costumes. We didn’t want to go as a pair so we decided she would go as a pilot and I would go as a slutty pirate or red riding hood. We also decided to take this to another level. We wanted to be as realistic as possible, but there was no real way to measure that. Lena decided that the first one of us who was able to get a ride home from someone of the same sex would win.
I wasn’t too sure about this. I mean her leaving with a woman dressed as a male pilot is one thing, but me dressed as a woman leaving with a man is something different. We agreed all we had to do was introduce our “new” friends to each other and the bet would be won, so I went along.
We ordered our costumes and after they came in, we both noticed they needed to be altered and adjusted. Lena’s needed a little more realistic padding in the chest and arms and she needed to sport a package down below. Her blond hair was short already so she decided to cut it a little shorter color it and style it like a military pilot would and the dark sunglasses hid those beautiful blue eyes of hers.
My costume, on the other hand, was tougher. Once it was on we both realized that I still didn’t look convincing, but Lena knew what to do. She grabbed a corset from the closet and cinched it around my waist. She adjusted the long skirt so they covered my legs – leaving the long slit up the front to show off my long legs.
She used her breast forms from another costume she had and put them in the bustier I already had on. So from the neck down, I looked more like a woman, but above the neck was a different story. I had to shave my beard and she came up with the idea to add hair extensions. I was closer but not quite there yet.
Lena said, “Don’t worry. I’ll figure this out.”
I wasn’t worried about it as we had pranked each other in the past; so, losing the bet was not a huge deal for me. On the day of the party, we started getting into costume. She, of course, was ready in a flash. I, on the other hand, was still struggling. Lena was fair and helped me get ready. She helped me with a pair of tan tights and then a black thong over the top. The matching padded bustier was next, then came the skirt and top. She then took the corset and cinched it around me accentuating my hips and bust.
“Remember, I do need to breathe,” I said as she pulled it tighter and tighter.
She had to help me with the boots since I could barely bend over. She then added the hair extensions and spent time on my make-up. When she was done I stood in the full-length mirror and was amazed at the transformation.
While I stood there admiring Lena’s handy work, she walked down to the car from our apartment.
As she walked down the stairs in full costume, one of our neighbors from a distance yelled out “Hey Mike.”
I couldn’t believe it – I lost the bet already. Lena just gave the neighbor a token wave and came back up to the apartment.
“Here ya go,” I said handing her the ten-dollar bill.
“Oh no, that doesn’t count,” She replied, “and you are not getting out of this one.”
“I think I am being set up here,” I said.
“You might be, but we’ll see at the party won’t we,” She said laughing.
We arrived at the party and we only knew the host so we were not concerned about being discovered. We mingled separately and I noticed Lena hitting the bar and talking to some of the ladies. I followed her to the bar and got a drink of my own and decided to talk to her instead of trying to win the bet. The bet was no longer the issue.
“Okay you win,” I said, “I don’t think I can go through with this.”
“Sure you can.” Lena replied, “Walk around a little bit.”
So I walked to a secluded corner of the house and stood there like a wallflower. Lena on the other hand really got into character. She started dancing with some of the ladies at the party. I was just waiting for her to bring one over so the bet would be over. No such luck. I needed another drink, so I went back up to the bar hoping to get closer to Lena so I could get her attention.
Then a voice from behind me asked, “Would you like to dance?”
I turned around to see a man dressed like a construction worker facing me. I didn’t know what to say. Before I could say anything, Lena walked over to the bar.
“Hey, Red. Are you doing okay?” She asked.
“Yeah, sure,” I replied
Lena looked over to the guy and introduced “himself”.
“Hey, I’m Mike,” Lena said
“Charlie.” The construction worker said as the two shook hands.
Then Lena looked at me grabbed her drink and said, “Red, come on you can’t just stand around the bar all night.”
I just looked at her with a stare that could eat through lead. Lena just smiled and walked away.
Charlie stepped closer and asked, “Your boyfriend?”
I don’t know why said it, I just looked at him and said, “No.”
Charlie’s facial expressions changed dramatically. He leaned over and ordered another drink and started to chat with me. We talked about a number of things. Where we were from, what we did for a living, what we did when we were not working… you know small talk. As he talked I appeared pre-occupied. I kept looking around for Lena who I now couldn’t find.
Charlie recognized it and said, “You don’t really want to be here, do you.”
“How could you tell?” I said smiling.
“It’s not too difficult to notice, but I know what you mean. I am only doing this because a friend conned me into it.” Charlie said.
“Same here,” I replied.
“Do you want to get out of here?” Charlie asked.
I wasn’t sure what to do. I kept looking for Lena, but couldn’t spot her in the crowd.
“I need to tell Mike,” I said – trying to find the right excuse to keep from leaving.
“It’s okay I am sure he’ll be fine,” Charlie said.
There was a part of me that wanted to just walk away. Another part of me was pissed that Lena just left me there. So I decided to go along with Charlie. If nothing else I would get a ride home and maybe win the bet in the process.
“Sure, okay,” I said.
I took his hand and we walked out together. We got into his car and headed to the apartment. The entire way he was looking at my legs, which were peeking out of the skirt and kept commenting on how pretty I was. When we arrived, I noticed the car wasn’t parked in our normal spot and figured Lena was still at the party. I texted her several times, to let her know I was heading home and how pissed I was she left me there alone but got no response.
Charlie walked me to the door and while I was looking for the keys in my purse, he said, “I had a really nice time.”
“Me too,” I replied still digging for the keys.
“Would you like to get together sometime for dinner?” he asked.
I was shocked. I looked up at him and he had this innocent look that just made me feel sorry for him.
“I don’t know, maybe,” I said
I had no intention of going out with Charlie, but I felt so bad for him. He was so pathetic. All he talked about losing his girlfriend to another woman and he was obviously lonely.
When I couldn’t find my keys, I went looking for the spare key in the plant next to the door. All I found was a note. “Sorry, lost my key had to take this one. – Lena,” I was furious. I knew I would have to go in through the patio, which was no easy task in costume.
“Let me do it,” Charlie suggested.
“No, it’s okay I can wait for my roommate,” I replied.
“It’s okay.” He said as he leaped over the fence enclosing the patio and walked in the sliding glass door. He opened the front door and said, “There we go. No harm done.”
I was so very grateful to him. I walked in and threw my purse on the chair and said, “Thank you so much. I really appreciate it.”
“No big deal,” he said. “Well, you are home safe and sound. I better get going.”
I felt so bad that he went to all the trouble… I couldn’t help myself. I stopped him and asked, “You don’t have to go yet, would you like to stay for a drink?”
“Sure,” he said as he shut the front door.
He sat down on the couch and I got a couple of beers from the fridge and sat next to him. I am not sure what it was, but I was really drawn to Charlie. He was quiet and shy and so sweet. I didn’t want him to get the wrong idea but at the same time, I didn’t want to shock him when he found out the truth. My hope was that Lena would come home and we would all have a nice laugh about the whole thing.
We continued to talk and drink for about an hour. I could tell he was way too drunk to drive so I figured he could just sleep on the couch. I would stay up so Lena would not be shocked by seeing him when she got home.
As we talked, he continued to move closer to me. Each time he moved closer I found a way to adjust and distance myself. I could tell he was getting tired when he dropped his head into my lap. I played along stroking his hair as he started to fall asleep. I got up carefully allowing him to remain sleeping on the couch. I went to the closet and grabbed a blanket and laid it over him carefully.
I then went to the bedroom and sat on the bed. I was so exhausted I just wanted to go to bed, but I was waiting for Lena to get home and I couldn’t get out of the corset I was wearing. So I just sat in bed for a little while and eventually dozed off. A little while later, I felt the bed move and thinking it was Lena and forgetting about Charlie, I didn’t react. The next thing I felt was a strong hand on my thigh. This was clearly not Lena.
“Can I join you?” Charlie whispered.
Still a little drunk and not quite clear of my surroundings, I didn’t respond and Charlie took that as a “yes”. He continued to caress my thigh and worked his hand up to my butt. I didn’t say anything initially, I was worried that he would reach between my legs and find a surprise. When he tried I immediately pulled away.
“What are you doing?” I asked.
“You didn’t say stop,” Charlie said.
“I’m sorry. I didn’t mean to lead you on.” I replied.
He started to pull himself off the bed and you could tell he was fully erect and I felt sorry for him since he was expecting more. He went back to the living room where he began putting his shirt back on and was preparing to leave. I looked at the clock and realized Lena wasn’t home and was not returning my phone calls. Now I was pissed and thought she should pay for this.
I walked out to the living room still fully dressed and caught Charlie at the door. I grabbed the back of his head and kissed him on the lips.
“What was that for?” he said.
“I feel bad and don’t want you to leave without having anything to show for it,” I replied.
I slid my hands down his shirt and began to unbutton his pants. He was trying to undress me and I stopped him.
“Nope… this is for you, not for me.” I said.
I continue to pull his pants and underwear down exposing his rock hard cock. I hesitated but filled with emotion I just couldn’t stop. So I licked my hand, took a grip of his cock and began to stroke it. He kept grabbing my head and I kept moving his hands to his sides. Then in one quick motion while gripping his cock I wrapped my lips around it and began stroking him with my tongue. Gently sucking him.
He quivered quite a bit but I just held him firmly. Pressing his crotch to my mouth as I slid his cock in and out of my mouth over and over again. It wasn’t long before he jerked quickly and before I knew it he shot his white-hot load into my mouth. I jerked back leaving the cum in my mouth and he continued shooting it onto my face. I had already tasted his cum and out of reaction for the taste, I left my mouth open hoping to catch more.
He took a hold of his cock and continued to stroke it squeezing out what was left and allowing me to extend my tongue for another taste. I finished him off and rubbed the cum from my face with his cock and licked him clean. When we were done, I got up from the crouched position, gave him a quick kiss and opened the door. He quickly pulled up his pants and headed out.
“You are amazing,” he said.
“You are not too bad yourself,” I replied.
“Can we get together again?” he asked.
“I’m not sure, but I will let you know,” I said as I guided him through the front door.
After closing the door, I rested my forehead against it thinking, “what did I just do?”
From behind me, I heard a familiar voice. “I guess you won the bet you whore,” Lena said.
I turned around to see Lena in the kitchen and she had come home found Charlie and me in bed together and decided to watch from a distance.
“I figured he just didn’t understand and was going to take advantage of how drunk you were.” she said, “but when you decided to give him a blow job, then I knew you were just as into it as he was.”
She walked up to me and put the ten-dollar bill in my bustier slapped me in the face and walked to the bedroom. I followed her in and tried to explain, but she wasn’t having any of it.
“Look you can be mad and you can leave if you want, but you left me there alone. Where were you when I needed you.” I asked.
She welled up and didn’t say anything, but with one look at her face… I knew.
“Who was he?” I asked.
She didn’t respond – just continued looking at me.
“She?” I asked
She nodded quickly wiping the tears away. She explained that she met a girl at the party and the two went to the back and ducked away to her place. By the time she had returned, I had already left with Charlie. She saw her phone but didn’t know how to tell me she had really hooked up with somebody.
“And you had the nerve to be angry with me?” I angrily asked as I threw the money at her.
“I never thought you would go through with it,” she replied.” To be honest, I didn’t think I would either… it just happened.”
We both stood silent for a moment. Then I sat down on the bed next to her.
“So what do we do now?” I asked.
“I am really sorry Mike,” she replied.
“Me too,” I said.
“I guess we just can’t forget about something like this can we.” She said.
“No, I guess not.” I replied, “but it doesn’t mean we can’t use it to our advantage.”
Lena put her arms around me and kissed me quickly then pulled away and walked me into the bathroom where she wiped away the makeup and got me out of the restricting costume. After we showered together, we went to bed where she treated me to the best blowjob I ever received… or gave. The next morning, she woke up in my arms and I gently rolled her over and let her sleep while I got up to make a cup of coffee. A few minutes later, she walked out to the kitchen in a t-shirt.
“I’m sorry, I didn’t want to wake you,” I said.
“It’s okay, I didn’t sleep that much anyway.” She replied.
“Because of last night?” I asked.
“Yeah a little,” she said.
We sat down and talked about what happened. We were still very upset at each other for the “mistakes” we made; but I also think we brought it on ourselves and in the process, we were willing to put it behind us. So much so, that we were willing to have a little fun with it.
“Want to try something different?” she asked.
“Sure why not?” I said.
“What if we got back into costume and went out?” she suggested.
“I don’t think that would work, we might stick out going to the club dressed as a pilot and pirate,” I replied.
“Not the same costume, but the same idea.” She said.
She had the idea that I would walk into a bar and she would come in an pick me up. I loved the idea but wasn’t sure how I would be able to pull that off. It is one thing to be in costume, another to try and pass as a woman. Lena wasn’t worried though; she knew exactly what to do.
So I went along with it especially considering the possible outcome at the end of the night. So we planned out date for the upcoming weekend and Lena was going to help me with my makeup and hair before she headed out, giving me full access to her closet and anything I wanted to pick out. Since we were the same size, anything I picked out was going to look great… at least I hoped it would.
That Saturday afternoon, Lena helped me get ready by fixing my hair and makeup and I helped her pick out something that would look nice, but a bit rugged and manly for her. She left wearing a pair of loose blue jeans and a dark blue dress shirt and my brown sports coat to cover her chest. She was very believable but looked more like a man with a feminine side. We decided to meet at a local hotel restaurant and planned to stay at the hotel overnight, so Lena packed a bag for us and took it with her.
After she left for the hotel, I made a b-line for her closet. I knew exactly what I wanted to wear; I was just hoping I could find it in the cluttered and packed closet. It took me a while, but I found what I was looking for.
I started with a pair of tan crotchless pantyhose to cover my legs and a black thong. I then found her waist girdle that she wore very few times and then moved back to my legs. I slid on a garter belt and some black stockings to further cover my legs. I grabbed her black lace, padded bra and after adjusting the straps a bit, I grabbed the blue dress she wore only once but looked stunning in. I hoped it would look good on me too, but not so well that it would draw attention to me… I was, of course, walking into a busy restaurant.
I put on a necklace Lena had laying around and wore her watch and a couple of rings, then needed to make sure I was comfortable, so I tried to find a pair of shoes Lena had that would fit… and after 20 minutes with no luck, I was frustrated enough to call the whole thing off, but Lena thought of everything and had left me a box on the kitchen table that she knew I would need; a pair of four-inch heels that were my size and easy to walk in.
I practiced a bit before leaving, then packed a small purse and sprayed on her favorite perfume and headed to the restaurant. When I arrived, I was still a little hesitant, but not enough for me to stay in the car. I jumped out and headed inside.
“Can I help you?” the hostess said.
“I am looking for my boyfriend.” I said as I looked around, “Oh there he is.”
I walked over to the end of the bar where I found Lena enjoying what appeared to be her third or fourth cocktail.
“I thought you would never get here.” She said.
“It took a little longer trying to find something to wear,” I replied.
“Well, you look great.” She said. She then leaned in closer and whispered, “That dress looks better on you than me.”
We both laughed about it as I ordered a drink. We stayed at the bar for a few minutes, where I was propositioned a couple of times.
After it had settled down a bit, Lena leaned in and said, “I can’t believe you.”
“What?” I asked.
“I come with you to a bar and no one tries to pick me up, but you…. I’m jealous.” She said.
“Shut up,” I said.
We were about to be shown to our table for dinner when there was a sudden hand on my back.
“I thought that was you,” Charlie said.
I was stunned.
“What are you doing here?” I asked.
“Meeting the two of you?” he said.
I looked over at Lena who had a sarcastic grin on her face. It was clear she had something else in mind for the evening. I became so nervous, I was tempted to leave the restaurant, but Lena and Charlie calmed me down as we moved to a table in the back of the restaurant.
“You look fantastic by the way,” Charlie said.
“Thanks,” I replied as I looked at Lena very angrily.
“Michelle thought it would just be the two of us for dinner, but I thought it would be nice to have a new friend along,” Lena explained.
“Michelle, huh…” Charlie said as he leaned over to me and whispered, “It’s okay, Lena explained it all to me.”
“She did? It would have been nice if she had shared that with me too.” I replied.
We continued through dinner where we all drank way too much. So much so that we were getting a little out of hand and were almost forced to leave the restaurant. After dinner and probably three bottles of wine, we left the restaurant. I was in the process of saying goodbye to Charlie when Lena interrupted us at the elevator.
“What are you waiting for, come on.” She said.
I looked at Charlie and then back at Lena confused.
“We better not argue with her,” Charlie said as he put his hand on my back and guided me to the elevator.
The three of us headed to the room, which Lena prearranged. The room was very nice and big. It was bigger than I expected. Lena took me to the bathroom, leaving Charlie in the bedroom alone.
“Lena, what are you doing?” I asked.
“I thought about the other night and I wanted to get a taste of what you enjoyed.” She said as she started to change clothes, “And what better way than to enjoy it with you.”
She quickly kissed me as she dropped out of the man clothes exposing the beautiful new lingerie she bought earlier in the day.
“Don’t worry about it, let’s just have some fun.” She said.
When she said that I was instantly turned on. I had never been part of a threesome before and my vision did not involve more than one stiff cock. She and I walked out to see Charlie standing in front of the window rubbing his cock through his slacks.
“Oh, are we neglecting you?” Lena said childishly.
She walked up to him kissed him passionately on the lips and immediately started to unbutton his pants. As she did she signaled me to stand behind him. As I did I started to massage his shoulders and back while Lena pulled down his pants.
Once his pants were down around his ankles, she went right to work. She took in every inch of his cock. As she did he began to fall back against my chest and my arms instantly wrapped around him. We managed to get him seated on the bed where Lena pulled his pants off and took me by the hand and positioned me behind her. She then bent over and continued to give Charlie a fantastic blowjob while I crouched down behind Lena and began to lick her pussy from behind.
As she began to moan, I could see Charlie’s legs start to rise. The oral pleasure was getting intense for both of them, so I decided to take it up another notch as I moved from her pussy to her ass. Penetrating her with my tongue at first then wetting my fingers and finger fucking her until she began to scream.
After several minutes of the oral pleasure, they were receiving it was my turn. Lena was already nice and wet, so she stood Charlie up and moved me to the bed. Lena never moved as she went down on me and pushed Charlie’s hard cock inside her from behind.
As Lena struggled to get words out of her mouth that was already full she mumbled, “OH FUCK THIS IS GREAT. I LOVE GETTING IT FROM BOTH ENDS.”
Charlie and I never said anything, but we just seemed to stare at each other as if we didn’t really need Lena.
“Come here Charlie,” Lena said.
She moved Charlie on top of the bed and moved close to my face – close enough for me to enjoy the rock hard cock Lena prepared for me.
“Oh yeah, baby, that’s it… you know what I like,” Charlie said as I pushed my tongue up against his cock as he slid it in and out of my mouth.
As I orally pleasured Charlie, Lena continued to take care of me. That went on for a few minutes when Charlie was ready, but Lena wasn’t done giving instructions. She pulled Charlie’s cock away from my mouth, which was not easy as I didn’t want to let go. She pulled my legs up in the air and pressed my knees up against my chest she then switched places with Charlie, straddling my face as he and his wet, rock hard cock was ready to fill my nice ripe hole.
As I began to lick Lena again, Charlie pushed his cock inside me. I couldn’t believe the feeling. I now knew why Lena enjoyed it so much.
“mmmMMMMM… YYYYEEAAAHHH…” I screamed.
“Give it to her baby,” Lena said.
“YEAH… YEAH… YEAH…” I shouted as he pounded me faster and faster.
“Do you like her virgin pussy?” Lena asked Charlie.
“Oh yeah… uh… uh… uh… I love that tight hole.” He replied.
“OH GOD…OH GOD… FUCK… YYYYEEAAHH…” I screamed with pleasure.
“Come on baby, cum inside her,” Lena said as she clutched onto my ankles holding my legs in place while Charlie continued to fuck me so damn good.
“UH… YEAH… FUCK ME… FUCK ME… HARDER… HARDER… HARDER… YEAH…” I begged.
“OH YEAH… YEAH… YEAH… AH… AH… AAAHHHHH… “ Charlie uttered as he came inside me.
As he did, I could feel his cock throb while he was still inside me. As it did, I shook in total ecstasy. Lena stepped away from me and carefully took Charlie out of me… licking the remaining cum off his cock and walking him to the bathroom. While I assumed she was cleaning him up, I was recovering from the pure joy of being fucked for the first time. I was exhausted and curled up into a ball and started to relax.
With my back to the door, I did not realize Lena had cleaned up Charlie and sent him on his way. I turned around to see Lena wearing a thick cotton bathrobe. Thinking we were done, I started to get up to get cleaned up my self.
“Oh… we’re not done yet.” She said.
“Really?” I asked.
She walked over to me grabbed my face and opened her bathrobe exposing her other surprise – a long black strap-on dildo. I wasn’t sure what she had in mind, but I wasn’t sure I had the strength to keep going… Lena didn’t seem to care. She pushed me onto my knees and proceeded to stick the cock in my mouth – over and over again until it was nice and wet. She then brought me to my feet and bent me over on to the bed. She squirted lube all over the strap on and pushed it inside me.
“You like that don’t you… you little whore.” Lena said.
“Yes,” I said uncontrollably, “I love it… FUCK… IT’S BIG… AH…UH… UH… UH…” I replied.
She poked me a few more times then yanked out and threw me onto my side. She then climbed up on top of me and rode me until it was my turn to explode.
“YES… YES… YES… FUCK ME, BABY… FUCK ME, BABY…” She screamed.
I never had to move as she did all the work and aggressively slid up and down my cock.
“I’M CUMMING… I’M CUMMING…. UH… YEAH… YEAH… AAAAHHHHHHH YYEAAHHHH….” I said as I came inside her.
She continued to ride me slowly as I jerked with every shot of cum that squirted out of me. She then fell onto me exhausted. The two of us just laid there for a few minutes before cleaning up and getting back into bed. The next morning, Lena was up before me and packing our things.
“Need some help?” I asked as I started to get out of bed.
“No, I am almost done.” She said.
“I am not sure how to explain last night Lena,” I said.
Lena crawled into bed with me and said, “We don’t need an explanation for last night, we just need to remember how great it was for both of us.”
“You mean all three of us?” I asked.
“No, Charlie was like the tool that needed to be sharpened…” she said, “…and you were a hell of a sharpener.”