Rick Needed a Beer, Gets Much More Pt. 11

This chapter may better fit in the cross dressing category, but I'm keeping it in Gay, as past and future chapters are gay stories. And this chapter does involve some hot gay sex. I recommend you read previous chapters first, if you haven't already, to understand the characters.

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Tuesday at the office was awkward, to say the least. I avoided Diane and stayed in my office, scared of what she may say or do. Has she gossiped about my pictures in makeup and lingerie? My purple lace panties? that I couldn't get it up?

Late in the afternoon she came in and said "Rick, I've always been attracted to you and liked you. Friday night will be an opportunity to find out if there is any possibility for us to have an intimate relationship, or if your interests lie elsewhere. I expect you to show up in full makeup and dressed, at 8:00, OK?, and I may have a surprise for you."

I got home and popped a beer. As soon as I took a swallow there was a knock at the door. I opened it to find Sue who rushed past me carrying a package and saying "follow me, come see what I got you" and she ran back to my bedroom.

Sue was all excited as she pulled a wig out of the box. "This wig is a copy of Marie Osmond's hair from her diet commercials, let's put it on and see how you look."

She helped me put it on and it did look like Marie's hairdo, long, wavy brown hair. "You don't look happy. I thought you would love it. What's the matter?

"Sue, thanks. I know you you mean well, but I think I'm happy being a man. The fact that I've come to love sex with men doesn't mean I want to be a woman. The worst part is I've been discovered by Diane, my secretary." I told Sue about what happened with her yesterday and how she expects me to come over Friday night in drag and I've decided that will be the last time I dress up, and how I've decided to take next week off and get away alone.

"Rick, what will you wear? You have all the lingerie you need, but you don't have a dress. You are too muscular to wear any of my clothes. Would you like me to get you a dress?

I told her yes, and she agreed to come over Friday evening and help me get ready.

The week flew by with me putting in long hours getting work done in advance in preparation for taking next week off. I did find time to book my flights and make reservations near a quiet, desolate Florida beach.

Friday evening arrived and I showered, shaved my body, and rubbed lotion all over, enjoying my smoothness. Sue came in and said "you look good enough to fuck!"

I noticed my cock start to harden and said "I would rather stay here and spend the night with you." I put on my black lacy panties, pulled on my stockings, loving the way they felt on my smooth legs, fastened them to my garter belt, and then put on my bra and falsies. Sue applied my makeup. I was amazed at how pretty, and sexy my eyes looked. She brought out a black dress and I put on a dress for the first time. It was really short, showing off my shapely legs, low cut highlighting my created cleavage, hugged my figure, accenting my ass, and had loose long sleeves hiding my muscular arms. I put on my 4-inch heels and the wig to complete the look. Looking in the mirror I almost didn't recognize myself.

Sue said "you look beautiful!"and started taking pictures of me with her phone and my phone, "if you are never going to dress up again you need a few pics to remind yourself of how sexy you look."

I was thankful that my windows were tinted dark as I drove to Diane's. She lived in a high rise condo downtown, which meant I would have to navigate the lobby and elevators. I parked in the visitors spot and walked into and across the lobby to the elevators. My high heels were loud on the marble floors. I ignored the stares I was getting from the security guard at the desk, and got on the elevator and pushed '7'. I made it to Diane's condo without running into any residents, and knocked on her door.

She opened the door, letting me in, saying "you look even more beautiful in person. I love your hair! Come in and let me get you a drink. What would you like?"

She told me to have a seat in the living room and went to get me a glass of wine. She had soft, symphony type music playing, which I never listen to. It did create an interesting atmosphere, and, after all, I was dressed for it. I sat on the sofa, and found sitting for the first time in a dress, crossing my legs like women do, a little awkward.

She came in and handed me my wine, sat next to me, turned towards me putting her arm on the top of the sofa and said, "tell me Rick, when did you start dressing like a woman? Is it a long time desire? Do you wish you were a woman? Do you have sex with men?"

We drank wine and talked, probably way too much, but when you are dressed like a woman, everything is pretty much out in the open. We were half way through the second bottle of wine when the doorbell rang. She said "don't get up" and jumped up, answered the door and let Danny in. I wasn't expecting anyone else to join us.

He said "Rick, I'm shocked, but you look absolutely fabulous!" He sat down on my other side and Sue got him a glass of wine and we continued to talk. It wasn't long and Danny had his hand on my thigh. I should have pushed it off, but I didn't. Maybe it was the wine, maybe it was because it felt good and I welcomed his advance. He turned towards me, putting one arm on the top of the sofa, around my shoulders, and the other hand was now rubbing my thigh more aggressively, arousing me. His touch felt sensual through the thin fabric of my dress. Sue got up to get more wine and as she left the room Danny pulled me towards him and kissed me full on the lips. I welcomed his kiss and we kissed deeply as he move his hand up under my dress, finding my raging hard on. The scent of his cologne and his kisses had me very aroused. I thought of all the times I had made these same moves on women in the past, only this time I have a man making the moves on me, the 'woman.' He was in control, making the moves, and I found myself being submissive, allowing him to have access to me. He pulled my panties down, releasing my cock from my panties, and started stroking it, saying "you've got a great cock."

I reached over and felt his crotch, like I always wanted women to do to me, finding his cock, and it was large and I knew I wanted it in my mouth and ass. He whispered in my ear, "suck my cock, Rick, you know you want to. I unfastened his belt and pants, opening them and pulling his nice cock out. I broke off our kiss and was starting to lean over to fulfill his wish and take his cock into my mouth when I noticed Diane sitting in the chair watching us.

She said "don't stop, this is what I invited you over for. You could have chosen me, but instead you chose Danny. I want to watch you suck his cock, and anything else you two decide to do."

I had his big cock in my hand and my gaze turned from her, to looking into Danny's eyes. He had that hungry, suck my cock look in his eyes and I leaned over and kissed the mushroom head, licked it from the base to the head, and then took it into my mouth, sucking, moving up and down the entire length. Surprisingly I felt no shame sucking his cock with Diane, my secretary, watching. Work would never be the same again.

Danny started having a conversation with Diane as I bobbed up and down the length of his cock. "Thank you for inviting me over. He is a great cock sucker. It feels awesome. you were right about him, he is gay, ooooh yesss."

I felt his cock stiffen and he exploded, shooting his hot load of cum into my mouth. I sucked him dry, milking every last drop. I sat back up on the sofa. Danny had that exhausted, satisfied look on his face as he lay back on the sofa.

Diane said "Rick, so you are gay".

"I do enjoy being with men, but I also have always enjoyed being with women, so I think I'm BI sexual. I would like to come over some time, dressed as a man, and just the two of us, because I find you to be a very attractive woman. I have an early flight in the morning, and it's getting late, so I need to be going." I leaned over and gave Danny a kiss and whispered, "we need to get together again" and I got up and left.

I pushed the down button and waited for the elevator to arrive, hoping I wouldn't run into anyone. The doors opened and I got on and pushed the lobby button. As the doors closed I noticed that the 20th floor button was lit as we started up. There was a really large man standing quietly. I said, "I wanted to go down."

I recognized him as the all pro defensive end on our local team. He responded "I would like that. I bet you would love to go down on my big black cock, wouldn't you?"

I looked at him and he continued "I'll take your licking your lips as a yes."

I replied "I'm not what you think I am."

"I know what you are, and I know what you need. You are a white faggot and you need my big black cock. You love sucking cock don't you? Have you ever sucked a black cock before."

The elevator doors opened and he grabbed me around the waist hugging me and walking me to his penthouse condo. Even with my 4-inch heels he was at least 3 inches taller than me. I liked the feeling of walking next to him, his strong arm holding me close.

We walked in and he immediately started to undress, and was quickly standing in front of me naked. He was fit, muscled, and had the biggest cock I had ever seen hanging between his legs, and it wasn't even hard yet. I thought to myself, how big would this monster get?

He said "on your knees faggot, I want my cock in your hot, wet, gay mouth. And if you suck it really good, I might even give you what you really want, a real ass fucking. You would like that, wouldn't you?

"Yes, I'd love to have you pound my ass with your monster cock." He sat on the couch and I got down on my knees between his legs and grabbed his soft cock, which was already at least 8 inches long. I leaned in and took it into my mouth and began to suck it, taking it all in, feeling it grow and stiffen in my mouth. It was stretching my lips as it entered my throat. It was fully hard now and I took it out of my mouth to admire it's enormous size, and asked "how big is it?"

"Eleven inches, now put it back in your mouth, cocksucker." Which I did, licking it and sucking it, moving down it's length, trying to take it all down my throat, bobbing up and down, making loud slurping noises as I got all but about two inches in, moaning on it. He grabbed my head and pulled forcefully, pushing his cock down my throat until my nose hit his firm stomach, saying "I knew you could take it all. Your throat is so tight and feels so good." He then began fucking my face, pumping his cock in and out. I could only accept him being in control and enjoy having the hard smoothness of his awesome cock moving in and out of my mouth, using me to bring him pleasure.

He started moaning and said I'm getting ready to cum in your mouth and I expect you to swallow. His cock got harder and I felt it pulse as it exploded in my mouth, huge shots of his seed, the biggest loud I've had the pleasure to eat. I swallowed and continued to suck his cock as he continued to cum. I slowed my pace and gently sucked him dry and licked his cock clean.

He said "suck my balls and I'll be ready to fuck your faggot white ass in a minute."

I leaned in and started licking and sucking his balls, looking up at him, as he watched me with a big grin on his face. I held his gaze as I sucked his balls, and his cock was moving, straightening, growing back to it's full glory, pointing at the ceiling. He said, "Suck my cock, spit on it and get it wet. I'm ready to fuck you. Get up and lean over the back of the sofa."

I got up and walked around to the back of the sofa and leaned over it. My ass and legs were flexed as I still had my 4-inch heels on. He pushed hard on my back forcing my face down onto the sofa seat and pulled the back of my dress up exposing my ass and black lace panties. He pulled them to the side, exposing my white ass and my speedo tan lines. He spit on my ass and rubbed it into my hole and began exploring, probing my man pussy with his finger, then two fingers, spitting again. He pulled his fingers out and I felt his massive cock start to push it into my hole. I concentrated on relaxing, welcoming his cock into me, filling me. He continued to push slowly until I felt his body against my ass, knowing that his huge cock was fully buried in me, I was overcome with that wonderful feeling of being full of cock. He started pumping his monster in and out, massaging my sweet spot with each stroke, sending waves of pleasure through my body.

He said "I like your girly bikini tan, your creamy white ass feels great, like it was made for my big black cock. You sound like you love me fucking your faggot ass, don't you?"

"Oooh yesss, I love you fucking me with your big cock, don't stop, it feels fabulous." I knew it wouldn't be long as I felt as orgasm building in my loins and my entire body was beginning to shiver as he continued to pound my ass, faster and faster. I could hear him breathing harder and moaning. He grabbed my hips and was making long, deep thrusts into me, when he pushed in deep and stopped, I felt his cock pulsing in me and could feel it exploding in my depths, filling me with his seed. This sent me over the edge and I was consumed with an intense orgasm, shooting my load on my stomach in my dress.

He withdrew and said "you are one great fuck. I want your number and I want you to come over again."

I didn't move. I continued to lay over the couch, exhausted, satisfied, in that post orgasm bliss. I felt his cum start to run out of my ass and down my leg and asked him to get me a towel. He got some paper towels and wiped his cum off my ass and legs and helped me back to my feet. My dress was sticking to my stomach where I had a large wet spot from my cum. He said "looks like you came in your dress. You must really love getting fucked by my big black cock."

"I did love it, but don't get a big head, I always cum from getting fucked. You should try it some time. Where's my purse? I need to be going."

"You didn't have one with you when we got here."

I left, knowing I must have left it at Diane's, and returned to her condo and knocked on the door. She opened the door and said "where have you been for the last two hours? We've been worried about you. Right after you left Danny noticed you had left your clutch and ran after you, expecting to catch you. He said he got down to your car and you weren't there. He waited 10 minutes and when you never showed up, he came back up. He just left 20 minutes ago. What's that wet spot on your stomach? Is it...no, did you cum in your dress?

I told her about my experience with the all pro and she said "tonight you've sucked two cocks and been fucked in the ass to orgasm, and you don't think you are gay? Why don't you except it and go with it. There is nothing wrong with being gay."

I told her I had a lot to think about and was looking forward to getting away to the beach tomorrow, and left, knowing I still needed to pack for my early flight.

I got home and walked into my master bath and admired how I looked in the full length mirror. I spun around to see how I looked from the rear and liked what I saw. Would this really be the last time I got dressed up? I looked myself in the eyes and thought that if I had been a woman that I probably would have been a whore, fucking every cock I could. Then I realized that was exactly what I have become, a real cock whore. In just over a month I've gone from a man that knew he was straight, to a cocksucker that loves getting fucked, and so far hasn't been able to say no. I took off my wig and put it back on it's holder, got undressed and removed my makeup. I quickly packed for my trip and went to bed, knowing my alarm would be going off in less than two hours.

And the alarm did go off way to soon, waking me from a hot dream of getting fucked by Tim. He was by far my best fuck of all time. I jumped up and took a quick shower, dried off and stepped out of my walk in shower to be face to face with Sue. I regretted having given her a spare key to my house. She said, "I knocked and when you didn't answer I thought you might be oversleeping. You look good enough to fuck. Do we have time for a quickie?"

She had on her signature outfit, spandex yoga capris and a sports bra, showing off her bare stomach and all of her great curves. I was standing there admiring her beauty and she said "your cock is answering for you", and pulled her sports bra off exposing her full, perky breasts. "I want that big cock in my pussy."

We jumped in the bed and started kissing passionately and my cock slid into her hot, wet, ready cunt. She immediately started moaning and wrapped her legs around mine. She was throwing her ass into every thrust I made, we were fucking each other like a machine working in sync with each other. Her pussy felt wonderful and I was soon unloading into her depths as she moaned she was coming. We kissed some more and I rolled off of her. She leaned over and sucked my cock, getting the last drop of my cum and licking my cock clean. She then moved up, planting her cunt on my face and said suck your cum out of my pussy and lick me clean" which I did, bringing her to another body shivering orgasm.

I jumped up and washed her pussy juices off my face, got dressed and said "we've got to hurry or I'm going to miss my flight.

Driving me to the airport she asked how my date went. I told her all about Diane, Danny and the all pro. She said "you really are becoming a cock whore. I never would have thought a man that loves men like you do could fuck me better than any other man ever has. How did you feel being out in drag? Was it exciting?"

"Yes, it was exciting in a different kind of way. I found myself feeling submissive, like what I would think a woman would feel like. Danny and the all pro both made me feel like I was there for their pleasure."

We pulled up to the gate and we got out. Sue gave me a big hug and kissed me deeply and said "I love how you fuck me and I have never enjoyed anyone's company like I enjoy being with you. I wish I was going with you."

I thanked her for the ride and confirmed she had my return flight arrival time for picking me up next Saturday.

As the flight took off I looked out the window and thought to myself that when I went to bed last night I was convinced I was GAY, and comfortable with it. Then Sue and I had great sex this morning, causing me to rethink my orientation. It will be great to be alone for a week, soaking up the sun, working on my tan and taking long, quiet walks alone on the beach, with plenty of time to think. My mind drifted back to the dream I was having when the alarm had gone off. I felt stirrings in my loins and caught myself flexing my asshole and licking my lips as I visualized Tim's tanned, hairless, fit body over me, his abs flexing with each thrust he made, driving his big cock deep into my ass, as I drifted off to sleep.

——————-to be continued——————-

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