A Surprise Relationship


Seeing this gorgeous woman sitting there with me, plus the alcohol I had in me, there were no more thoughts of this being Tony. I broke our kiss and stood up, seeing the sad scared look on her face. I knew she was thinking I didn't want her, because she wasn't really Kim. But she was wrong. I wanted her as much as I had ever wanted the real Kim, and I didn't care who she had been born as. I proved this to her by picking her up from the couch and carrying her to my bedroom. Her arms went around my neck again as she realized where I was taking her, and I felt her tears soaking through my shirt as she pressed her face into my shoulder.

I gently placed her on my bed before we started kissing again. My hands slid up under the hem of her dress and along her thighs as her hands worked at the buttons of my shirt. As she pulled my shirt off of me, my hands went to her waist, where I felt something under her dress, before sliding up her back to undo the clasp at her neck and then down to lower the zipper on the dress. I helped her stand and watched with awe as the dress slid off her body, exposing her body to me. She stood there in a black thong and stockings, which were held up by straps attached to a black corset, which held her 'B' cup "Real Breast" breastforms perfectly in place.

"Wow!" was all I could say as I looked at her. She told me that she found a store that sold corsets, and bought one to give her body a better shape. They had helped her put it on at the store before she went shopping for her dress, as well as a few other outfits which she would show me later. She had to remove it at the salon, but one of the girls there helped her put it back on before helping her with the rest of her outfit.

As she told me this, her hands worked on undoing my belt and pants, allowing them to drop to the floor before she looked at the bulge tenting out my boxer briefs. I had been at least semi hard since she had walked out of the mall, but now was fully erect, and my shorts were wet from pre-cum dripping out. She turned us around so the back of my legs were against the bed and softly pushed me, making me sit on the edge. She then knelt on the floor in front of me and reached for the waistband of my shorts, slowly pulling them down my legs until they were on the floor with my pants and shirt. Her breath was warm, and her tongue warmer, as she moved up from my knees to my crotch. Her hand moved my cock out of her way as her tongue moved over my balls, lathering them with her saliva before taking each into her hot mouth and sucking on them.

She continued to hold my 8" cock in her hand, slowly stroking it and softly squeezing it, as her tongue moved down my other leg to my knee, then back up to my crotch. Her tongue dragged up the underside of my shaft, circled the head, and licked the pre-cum that was seeping from the pee hole. She licked up and down and all around the shaft and head, taking her time and driving me crazy. My hands moved along the soft skin of her arms and over her shoulders to her head. My fingers wove themselves in her hair as I tried to guide her to take my hardness into her mouth, but she wanted to tease me more. She licked her way back down to my balls, again sucking them into her mouth before gently biting the skin of my sack, before licking up to my stomach. Her tongue tickled as she barely touched my skin with it.

Her hand was still gently stroking my shaft, and she surprised me by suddenly enveloping it with her mouth. Her mouth moved up and down, slowly taking more of me in until I was touching the back of her throat. The suction she had on me was amazing, and the way she used her tongue around my shaft was almost enough to make me cum. But she knew what she was doing, and kept me right on the edge, letting it build, for almost 10 minutes. She flicked her tongue over the tip of my cock, then used the tip of her tongue lightly circling the head before sucking it back in fully. I was so close and could feel my sperm building to explosive levels. Kim could feel it too, and surprised me by pushing her finger into my ass as her mouth slid back to hold only the head in. Her finger was enough to push me over the edge, and I exploded, shooting almost a year's worth of cum into her mouth. She continued sucking and stroking me until well after I was empty, and my dick started to soften. She let it slide out of her mouth then moved up my body and kissed me, passing some unswallowed cum into my mouth, which I hungrily swallowed.

We lay on the bed kissing and holding each other for about 15 minutes, letting our hands explore each other's body. My hand slowly moved down her side and over her hip before following the strap to the front of her thong. She quickly reached down and stopped my hand from exploring any farther.

"Terry. You don't have to. As much as we both want me to be, I'm not Kim. You don't need to do anything for me. Just let me enjoy what we've had. It has meant so much to me, more than you could ever know, everything you've done for me. I loved everything about tonight, but especially that you've treated me as the woman I want to be."

"Tony. I know that you're not Kim, and you will never be able to replace her. That doesn't matter. Yes, physically I've been attracted to you because of your resemblance to her. But I've gotten to know you over the last two months. You are so much like Kim in so many ways, yet you are different from her in so many more. I was in love with Kim. I was so in love with her that I was planning on asking her to marry me. But things happened that changed all of that. And now, you coming into my life has changed everything for me again. When I saw you walk out of the mall tonight, I didn't see Tony or Kim. I saw a gorgeous woman who had spent hours preparing for a night out with me. I saw Anne.

"Over the last two months, I have gotten to know you, and the feelings I have are for you. I have been thinking a lot over the last couple of weeks. I've been confused about my feelings. Tonight as we talked during dinner, I realized that those feelings have nothing to do with Kim, or anyone else. They are for you. It doesn't matter to me who you were born as, or who you want to be. It's surprised me, but I am falling in love with you, and the person you already are.

"However you choose to live your future -- as Tony, as Kim, as Anne, or as someone else -- it doesn't matter. My feelings are for you, and I will be here to support you 100%, no matter what you choose."

"OH MY GOD!!! You really do mean that, don't you?" she asked me.

She reached her arms around my neck and held me tight as she kissed me, her tongue pushing its way in to my mouth. I could feel her tears against my cheeks as we kissed. I also felt her hands slowly start moving down my body and one of her stocking covered legs sliding between my legs. She rolled us over so she was on top of me, and slowly slid her satin covered body down my naked body until she took my semi hard cock back into her mouth. The suction, combined with the warm wet softness of her lips and tongue, worked its magic on me and I was soon fully hard again. She licked all over the shaft before circling the head and teasing the sensitive underside before flicking her tongue over the pee slit, collecting some pre cum from it.

Anne then slid back up my body, one hand still softly stroking my shaft, and again kissed me, letting me taste my pre cum on her tongue, before breaking our kiss to look into my eyes.

"Make love to me, Terry. Please? I've never had a man make love to me before. I've given BJ's and hand jobs, but I've never had a man, other than..." she started to say, but couldn't finish. Tears formed in her eyes and I kissed them away before she continued. "Please Terry. I know how much you do love me and care about me. Please make love to me and make me a woman. I want this from you."

I kissed her again before I rolled her onto her back, and I slowly moved down her body, kissing my way down until my face was even with her thong. I could see a small bulge under it, and, even though I had never done anything with a guy before, it felt right to stick my tongue out and trace it along her satin covered bulge. My mouth opened and I sucked on her clit through the thong, making it harder. My hands moved to the waistband and I gently pulled the thong off of her, and I was staring at the first cock I had ever seen close up. It was about 6" long, and not very thick, and was hairless, except for a thin one inch long 'landing strip' of pubes above it. I ran my tongue along her skin under the bottom edge of her corset, over her sensitive stomach, before sliding it down to where her thigh met her crotch. I ran my tongue up one side, crossed over just above her pubes, then down the other side before licking up and down her inner upper thighs. I would stop just millimeters from her nut sack, and switch to the other thigh. I continued alternating like this for a minute or two before allowing my tongue to slide up her hairless scrotum and the underside of her clit shaft and head until I felt her pubes.

I teased her small patch of pubes for several seconds before my mouth opened and I slid my mouth over her clit, the first time I had ever had a cock in mouth. I held it in my mouth for a second or two before I started to explore the feel and taste of it with my tongue. It felt and tasted like nothing I had experienced before, and I found that I was enjoying this new experience. I thought of the blow jobs I had been on the receiving end of, and tried to do to Anne the things I had enjoyed the most. Her soft moans and gasps told me I was doing it right.

I eased off when I knew she was getting close to cumming, and moved down to lick her sack, gently sucking first one, then the other, then both of her nuts into my mouth. I used my tongue to play with them in my mouth before I released them. I pushed her legs up and licked down across her perianum until my tongue found her boy pussy. I rimmed her for several seconds until I felt her sphincter muscle relax and pushed the tip of my tongue through it. I gently jabbed the tip in and out of her hole, opening her and wetting her enough for me to slide one finger, then a second, into her tight hole. I gently moved my fingers in and out of her, opening her and relaxing her hole for what was soon to come. I carefully added a third finger into her boy pussy as I again began to suck on her boy clitty, wanting to taste her cum.

I felt something with my fingertip, and knew I had hit her prostate when her body lifted off the bed and she cried out as her cum began shooting into my mouth. I swallowed as much of it as I could, but there was a lot, as she hadn't cum in several months, and some leaked out from my mouth. Although I had tasted my own cum many times before, Anne's taste and texture was much sweeter than mine.

Anne pulled on my shoulders, wanting me to kiss her. I slid my fingers from her hole and moved up her body so she could taste herself in my mouth. She licked around my mouth, getting the cum that had dribbled out, and shared it with me.

"Please Terry," Anne said after breaking our kiss. "I'm ready."

Report Story

bycanuckCD© 2 comments/ 67783 views/ 34 favorites

Share the love

Similar stories

Also in this series

Tags For This Story

Report a Bug

2 Pages:12

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartbarzulboy, raysaab007 and 32 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (2 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (2)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: