With Her Blessing

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Kyleigh collapsed on top of him with him still inside her. "Oh, my God! That was amazing, honey!" she told him as she kissed him.

She was so caught up in being loved as a woman, she'd lost track of time. She didn't hear the front door open, but she did hear it close. As she looked up, Vicki was walking past, a big smile on her face as she put her finger to mouth and whispered, "Shhh!" to indicate there was no need to speak. She could see Kyleigh's bare arms wrapped around her boyfriend's neck and there was no need to explain what had just happened. Vicki winked and quietly headed upstairs as Kyleigh reveled in having made love with a man for the first time.

"Thank you," she said sweetly as he withdrew from her.

"My pleasure," he replied with a smile.

"I could get very used to this," she told him smiling back at him.

He went to remove his condom but she said, "Uh-uh. Let me get that for you, okay?"

She gently lifted it up and sat it on the floor next to her then took his softening cock in her hand and lovingly cleaned it off with her lips and tongue. "Mmmm. You taste so good!" she told him. "Do you want to take a shower now?"

"Only if I can take one with you," he told her flashing that wonderful smile her way.

"I think that can be arranged she said," as she stood and took his hand.

"Come with me, okay?" she said as she led him to the downstairs bathroom where she turned on the warm water. She took off her bra and breast forms, stockings and heels, and waited for him to open the shower door.

When he did, she stepped inside, turned around and waited for him to join her and to kiss her again. Thirty minutes later, they were both freshly showered and Kyleigh had again been freshly fucked.

Life with Vicki went from good to better over the following weeks and months as Kyleigh was able to make love at least one or two times a week, and Vicki had gotten a lifetime reprieve making them two very happy girls.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
15 Comments
1Martiniman1Martinimanabout 1 month ago

Good writing, but honestly a sad story.

FatSexLoverFatSexLoverover 1 year ago

Many thanks komrad1156 for writing my life story, your writing is easily read while being amazingly well written, so with many praise for your story, that also happens to be my life story so i am thankful for you writing this there i say it master piece! Good vibes and wishes

CindyTVCindyTValmost 2 years ago

Great story line, fun story. 5 Stars

Riki1942Riki1942over 4 years ago
Wonderful Story

What a wonderful story! I can relate to the part about being so overwhelmed with joy and pleasure that "she" wanted to cry.

I'm not overly emotional about these things but, the first time I made love as a woman, I felt the same way. I was down to my silicone breast forms, bra, miniskirt, crotchless pantyhose, sheer nylon panties and heels when I took his cock into my mouth. The thought of what I was doing, seeing my lipstick on his shaft, the feel of his hard cock in my mouth combined with the taste of his delicious pre-cum and him holding my head like I was his woman while I sucked him, was soooo wonderful and overpowering that I had to stop because I didn't want us to cum that way.

I had longed for so long to be made love to while dressed, and be impregnated as a woman, that I told him that I wanted him to do it to me without a condom and cum inside me.

We didn't make it to the bedroom either. He laid down on the couch on his back, I climbed on top and straddled him with my pantyhosed legs and heels, pulled the crotch of my panties to the side, guided his cock to my "pussy" hole and lowered myself down on him.

I came first, with my load oozing out through my sheer panties, without my cock ever being touched, like in your story. When he started to cum. I sat down all the way, getting his cock as deep inside me as possible while he bucked his way through his orgasm inside me. It felt so WONDERFUL as he lifted me up with each orgasmic thrust against my bottom, and the knowledge that his sperm was shooting deep inside me was so fulfilling and what I had craved so badly for so long, that I started sobbing like a baby and ruined my eye makeup!

He was my first long term lover and we never did use condoms. He was the first guy that I had sex with while crossdressed, sucked without a condom, learned that I loved the taste of pre-cum and, eventually, that I learned how much I liked to make him cum in my mouth and swallow! We fucked like bunnies several times a week for three years, until he moved away because of his job.

Riki

tg56boytg56boyover 5 years ago
Great story.

I, too am a cross dresser. My wife and I have a similar arrangement. After a few years of dating other men, I now have a boyfriend. My wife allows me to be with him and we even go on vacations together. My wife is so supportive of me in this, she is looking into having my boyfriend and I have a symbolic wedding in Mexico this spring. My wife and I have been married for 20 years now and we hope for more. My boyfriend and I have now been going out for six years. I have really come to enjoy being the woman in his life. Our sex life is fantastic. I love it when we have intercourse and he cums inside me, I feel so good when that happens. I also like giving him oral stimulation. Just recently, I started tounging his anus, it brings him to such an orgasm.

cdCindy1cdCindy1almost 6 years ago
wonderful fantastic story

I too am a married CD who hasn't had sex with his wife in a long time. This story is exactly what I would love to happen with my wife. It would be the best of all worlds for her to first find out about my cross-dressing (she doesn't know yet) and then when she found out for her to suggest that I get a boyfriend -- well, that would be MY ULTIMATE DREAM !!! Unlike Kyleigh, I have already sucked many cocks and have already been fucked by big hot handsome hunky men. I am so attracted to men that even though I'm still attracted to women as well, I don't mind thinking of myself as "gay". It's wonderful being with a man when I'm dressed as a woman but lately I've also been with men fully naked - no clothes, no women's clothes, no crossdressing -- just 2 hot naked men having hot gay sex.

Anyway, this story really turned me on and made me so hard that I came into my hand and ate it all up. Now I need to find a man to be my regular boyfriend. It would be great if my wife knew but alas that will have to wait for another day.

One of the best stories on Literotica -- thank you very much for writing it.

DeborahAnneDeborahAnneabout 6 years ago
My dream also

I am much older, a bisexual cross dresser also with a wife who allows me to dress here at home, the only thing is she has no idea I want a man like Kyleigh found who would do me just like he did to her, Kevin sounds like a very nice man for sure. Sometimes my wife visits her father and that is the time I wish I could find me a willing man.I so love to give oral and receive in my cute little butt. da.cd@frontier.com

GeorgiaDGeorgiaDabout 7 years ago
Every girl's dream

Such a lovely story and well written. It's a dream that most Tgirl's will have had at some point, and some lucky one's will have experienced, though probably not with their wife watching. Maybe one day I'll be the one sitting on a lap..

More please! G xx

LovinhoseLovinhoseover 7 years ago
Great story.

I do have to disagree with the 'statistics', as they were never properly executed! They sampled certain demographic areas that are KNOWN to be predominantly 'straight' crossdressers, and the samples were very small to boot (similar to political polls where they poll 1,000-1,500 people. Had the polling been conducted EVENLY across the country and ALL demographic areas, the result would have been much more realistic. The choice of which areas to survey was influenced by a group of straight crossdressers who did NOT want the real statistics to be revealed for fear of being labeled as the majority rather than the minority. The actual fact is that a majority of crossdressers are NOT straight! A majority of crossdressers are BISEXUAL, ranging from acting upon bi-curious tendencies all the way to almost gay where the crossdresser IS attracted to women but would rather have sex with men while dressed. I myself am bisexual, and I haven't met a straight crossdresser in my life to this day. I tell you this for a reason...because you shouldn't be ashamed about having desires for sex with a man. It's not bad, it's not guilty, it's amazing and incredible, and you should never avoid acting upon a desire because of what 'most people think' is right or wrong! Go for it, you will NOT be in the minority. One in four men crossdress! Think about that...out of a crowd of 100 men at the hockey or football game...25 crossdress! Of that 25 crossdressers, more than half are bisexual. I can't tell you how I know what I know (not allowed to), and you can doubt me or call me names or a crackpot (been called a lot of things by people who don't want the TRUTH getting out there), but I can definitely tell you that the 'statistics' you have been lead to believe for so many years are false and non-representative of the entire country. They have an agenda to cover up the truth.

Anyway, loved your story, it's a lot like my story! My wife is not quite as understanding, but has traded sex with her for my freedom to pursue (without her knowledge, she doesn't want to know) my life as a woman when I can. I can't bring anyone home but I have my fun I can tell you, and much like your story (is it true?), I much prefer it this way, I'm more than happy to give up sex with my wife in return for being able to have sex with men as a woman! Thanks for an incredible story, hope to read more.

DianeRedfernDianeRedfernover 8 years ago
Made me SO wet

Just loved it. Very nice deflowering, perfectly done, one layer at a time. Very nice exposition. Would love to read more.

xoxo,

Di

Show More
Share this Story

Similar Stories

My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
A Boiled Frog Pt. 01 Wife slowly brings husband into feminine lifestyle.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Wife's Idea Wife teaches Hubby new tricks.in Group Sex
More Stories