The Drake

Story Info
Wife's ex-boyfriend teaches her husband about womanhood.
3.3k words
4.31
29.8k
43
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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
CindyTV
CindyTV
1,919 Followers

Hi Girlfriends,

I hope you're having a fun and wonderful day. This story is for all my sexy girlfriends out there. The ones that sometimes enjoy fantasizing, and playing with themselves. What inspired me to write this, is the new 10-inch monster dildo that just came in the mail. My wife Julie named it The Drake, after her ex-boyfriend Drake! She named it because it was close in size to his massive cock.

I've never had one inside me this large and didn't think I would ever be able to take it inside. However, I thought that if I was excited enough, I might be able to take it all in, and made it my personal goal. So I created this audio story, and made it lead up to just the right moment and,,, it worked. And it was amazing. I would love to hear some feedback, so please let me know how it goes. Enjoy and kisses to everyone from your friend, Cindy Johnson. (Free Audio MP3 version available upon request.)

THE DRAKE

"Honey, you look so cute in that lingerie set, and the garters and stockings give you such an extra sexy look. Now, I want you to keep those heels on the entire time, because I want you to know how it feels to get, fucked in them," said my wife Julie.

It's almost time baby. You've been dreaming and fantasizing about this day for so long, how does it feel to know that in a few minutes my ex-boyfriend will be mounting you? I hope you're ready to suck his cock, because he told me he is really looking forward to having my husband sucking him off, as I watch."

"I'm scared, Julie. Can we back out? I don't want to do this anymore!"

"Nonsense! We both know this has been your dream, and something you've been wanting to do for years. Just the other day, you even told me how much you were looking forward to becoming a complete woman and having a guy come inside you.

Well, tonight you become a woman. It's too late to back out now, and besides, you look so pretty. I know Drake is going to go wild when he sees how sexy you look in this outfit, and all made-up, like the sexy slut you are. Nope, no going back now. Drake is almost done with his shower and I'll expect you to treat him like the perfect lady.

Cindy, this will be simple if you follow my instructions. When he comes in the room, you are to act like his loving girlfriend, and like he's been out of town for two weeks on business. I expect you to show him lots of attention and show your appreciation for him tonight. You will give him lots of kisses, tease him as you know-how, and get him nice and hard.

I'll be watching and when I give you the cue, I will expect you to take his cock into your hand and show him how much you love it. You will rub it, kiss it, moan, lick it, and take it into your mouth. You will make love to it like it's the most wonderful thing you've ever seen. While you are sucking and licking it, I want you to look up into his eyes, so that he can see how much you really do love it.

And don't think about anything else, because after you get him hard and excited, he will take control and make love to you, like the girl you've always wanted to become.

Tonight you find out what it's like to have a man inside you, and what being loved by a man feels like. When you feel him erupt deep inside you, and then when he fills you with his seed and his hot come, you will become one of us, a woman.

Oh, did you hear that Cindy? I think he's done, and he'll be with you any minute now. Let's touch up your lipstick and then get you in position. I just love the color on your lips, you look so kissable. I hope after tonight you don't fall in love with Drake, he can have that effect, I should know."

Julie touched up my make-up and hair, sprayed some perfume on my pulse points, and had me lay down seductively in my sexy lingerie and high heels. She gave me a gentle kiss and smiled when we heard him at the door.

"That's him knocking on the door. Just lay back and put your head on the pillow, cross your ankles, and I'll let him in.

"Just a minute, Drake! OK, here we go, Cindy. Enjoy!"

Julie opened the door and Drake stepped, naked and towering over my sexy wife. My heart raced when he gave her a long kiss while wearing nothing but a smile, and showing off his own massive penis. Drake was at 6 feet 4 inches and 275 pounds of muscle, with an equally gigantic 10-inch cock.

I surprised myself when I realized that I found him to be very handsome. He took her into his arms and gave her a deep, long kiss, and as I watched in horror he placed his hand on her breast, as they continued to make out. I saw Julie reach down and rub his cock, and then lead him over to the bed. I didn't expect my wife to let her ex-boyfriend touch her like that, but there was nothing I could do except feeling a deep pain of jealousy, in my stomach.

All that went away when he looked down at me, and then back at Julie. "Wow, you're right baby. He does make a beautiful girl, and I'm honored that I get to be the one to take her virginity." He kissed Julie one last time, as she departed to the love seat across the room.

"Hello, Cindy. He said as he took my hand and rubbed my nylon-covered legs with his big, strong, hands. You are one sexy little girl."

I remembered what Julie told me to do and let my inhibitions just melt away. I sat up and grabbed him around the neck and drew him to my lips. He kissed me gently at first, and then harder until I felt his tongue parting my lips. Soon his tongue was in my mouth, playing with my own tongue as we exchanged a prolonged, sexy kiss.

His strong hands continued rubbing my legs and ass, which made me forget that Julie was there watching, which allowed me to tease him and touch him all over. I even started kissing his nipples on his massive chest as he rubbed my pantie-covered ass, and played with the garters on my stockings.

"Cindy, I love how sexy you look in those stockings, and the high heels are a nice touch, that really turns me on," he said as he gently placed my hand on his enormous cock.

Remembering what Julie said, I took him in my two hands after I moved down on the bed. I was now between his legs and stroking his shaft. I watched him smile as he lay back on the pillow. "Very nice! Keep it up, baby."

I stroked him, and after some time I got up the nerve to lean down, and gently kiss the head of his cock as I looked up into his eyes. He smiled when I did that, and he let out a gentle sigh. Oh, you're good. He moaned as I felt his body relax. I looked down at his giant cock and saw my lipstick on his shaft which caused me to smile, and realized that I had just done something I could never take back. I just had a man's cock in my mouth and realized that I kissed and sucked it. I had become a cocksucker, and that was something I knew I could never take back. For a second, I wondered what would Julie think of me now, for only a brief moment as I continued to marvel at his massive tool.

I must have been looking at his cock for some time because I felt a gentle hand on the back of my head and heard Julie's voice.

"Come on honey, it's time to show Drake how much you want his cock. She pushed me down until my lips were kissing the tip of his cock again. Open up, baby. Time to suck on that lovely cock again, but this time I want you to stroke his shaft as you suck him at the same time," she whispered in my ear.

I opened my mouth as wide as I could, and felt his hot shaft enter my mouth, but this time it was even bigger, and I could barely get my lips around it as I tried to make sure my teeth didn't get in the way.

"Very good, Cindy. Keep sucking him just like that, and keep stroking. You'll get the hang of it soon enough."

I did, and after several minutes my mouth got used to his giant cock, and I felt my head moving up and down his massive cock head, as my hand pumped his long shaft. I was rewarded with loud moans from Drake, along with some encouragement, "That's it bitch, keep sucking just like that. Oh Fuck Baby, you're a great little cock sucker!"

He moaned even louder and started moving in sync with my head bobbing up and down. The texture of his hot cock in my mouth felt amazing and turned me on even more than I thought was possible. I wanted him to come in my mouth, I wanted to taste his hot cum and tried to make it happen, but after several minutes, he just pulled his cock out of my mouth, and got up on his knees.

Julie was right again. Once I started sucking his cock he took over and took full control of the action.

"Oh Cindy, I want you baby. It's time for you to become a woman! Get over here and lay down," he said as I moved up on the bed to where he pointed.

Drake removed my panties, and then placed a large pillow under my ass. He had me in a position that exposed my boy pussy, as my legs were positioned upward with my high heels on the mattress. I was completely prone in that position, and totally in his control.

Julie was there helping him position me, and then I saw her grab a bottle of lotion, to make sure I was lubed properly. After she was satisfied, she put some on his cock and stroked him while I watched. I started to panic as I realized what was about to happen. After she was satisfied that he was as hard as possible, she positioned herself next to me, watching and whispering things into my ear.

"Cindy, it's time. You're about to become one of us, baby, and there is no going back from this. Once he fucks you and comes inside you, your manhood is gone forever. You are now a cocksucker and in a few minutes, you will be a complete girl, just like me. I hope you're ready."

Before I could answer, I felt Drake getting in position between my legs, and his strong hands moving over my garters. He easily lifted my ass even higher, positioning me to receive his cock, as I tried to balance on my heels. I realized again that I was totally helpless. I was about to tell him to wait until I felt the tip of his cock pressing on my opening. There was no way he was going to fit that thing into my tight boy pussy, and I shuddered in fear.

I turned to Julie and said panicking, "He's too big, he won't fit!"

Julie just laughed and giggled, "Don't be silly. He knows what he's doing, but you have to relax and let it happen. If you struggle and tighten up, then it will hurt. You have to relax, think like the girl you are becoming, and relish his large cock. Think about how wonderful you will feel once he's inside you, and how loved you will feel when he fills you with his hot seed. You are about to become the girl you've always wanted to be, Cindy.

I felt even more pressure and tried to relax. He was pushing slowly as I felt the tip of his giant cock spreading my hole. The pain was starting to overwhelm me as I felt tears forming and starting to roll down my face.

Julie came over and started playing with my nipple through my nightgown and told me to take in every sensation. "Cindy, I want you to remember everything baby. Pay attention to every little sensation. You will always remember your first time."

Drake realized I was fighting it and spoke up. "Cindy, here's how this will work. I'm going to spread your ass and push my cock head just inside you and from then on, you will be in control. You will push yourself onto my cock, until I am completely inside. You can push into me at your own pace, there's no rush darling, I want you to enjoy this, and remember these wonderful feelings, forever. Now just relax and try to feel all your muscles relax at the same time.

I did what he said, and once his head was just past my opening, I forced myself to relax and the pain slowly went away. After several minutes, I started to move down on him very slowly.

Julie encouraged me again. "That's the way baby. Take his cock inside you. Feel your man. Become his girl. Learn what it's like to be a woman. Become the girl you always wanted to be, baby., It's time. I love you. Let him make love to you," Julie said as she continued to talk to me and play with my nipples.

I kept pushing down, and suddenly without any warning, the head of his massive cock slipped through my opening and he was now inside of me. The feeling was overwhelming. I felt satisfaction, and euphoria all at once, and I let out a scream. I didn't move for several moments as I laid under him feeling him deep inside. It was wonderful, it was what I've always dreamed it would be like. I opened my eyes to see him just over me smiling as he leaned down and kissed me gently as I parted my lips.

"You're doing great baby, and you feel nice and tight. Now, Just let yourself get used to it and try to relax and enjoy me being inside of you." I didn't move, and I smiled as Julie nibbled on my ear and continued to pinch my now tender nipples, taking my thoughts off the large cock that was throbbing inside me.

"Cindy when you're ready, push a little harder and try to take as much of me as you can inside you. The worst is over, and it gets fun from here on out." When the pain was starting to subside, I did push, and the lube helped his shaft move freely inside me until I felt the entire weight of Drake pushing done on me, as he was now, deep inside me. We were now one!

Julie saw things progressing and said, "Look into his eyes Cindy, and show him how much you appreciate him fucking you like this." When I looked up at Drake he reached down and kissed me again. Julie kept playing and teasing me, by running her hands over my nylons legs, pinching my nipples, nibbling on my ear, and talking dirty to me the entire time.

I leaned up with my arms around his neck, thanked him, and passionately kissed him. As we kissed, I felt Drake start to move his cock in and out of me, and for some reason, all the pain had disappeared and was now replaced by a warmth, and a connection to another human being, that I had never felt before. It was like, Drake and I were one, Attached and in sync. Coupled and now part of each other, we were one. All these feelings grew and took over my entire body until I felt safe under this massive, handsome man.

After a while, I heard myself moan with pleasure, and I even heard myself encourage Drake to fuck me harder. "Oh Drake, you feel so wonderful. Don't stop baby. Fuck me, please., Fuck me, yes., Oh my god, I love this, Come in me baby, come in me please, let me feel you come inside me!"

Drake stopped kissing my neck and lips and moved up on his massive arms. He was now looking down at me with a smile and started to unleash his full rhythm, and fuck me into wild bliss.

He even felt harder and bigger than before, as I now happily accepted every thrust with gratitude, and didn't want him to stop. He continued to fuck me harder and faster, and then he looked down at me, with a heartwarming smile.

"Cindy, I'm going to come in you baby. Are you ready for your man? Tell me what you want baby."

"Oh Drake, come inside me! Please give me your seed! I want to feel you inside me, baby!"

He closed his eyes and started jerking wildly, delivering unbelievable strong thrusts, as he buried himself deep within me. I felt his balls hitting my ass and his large cock deep inside me. I heard him gasp, let out a low growl, and then felt his massive cock explode inside me. I felt his warm seed deep inside me and that gave me a wonderful feeling and made me smile with a satisfaction I had never known.

Julie was right. At that exact moment, I felt like a woman. I felt true love. I never wanted that moment to end. It was magical, and I cried with happiness as he continued to unload more and more of his seed inside me until he finally collapsed on top of me. With his full weight holding me down, I didn't move for several minutes. I felt tiny under him, as he was still buried deep inside me. I just ran my fingers through his hair, and whispered, thank you, in his ear. I felt every twitch of his cock, and after a long time, I felt him start to soften until he pulled out several minutes later.

"Wow, that was great baby!" He said, giving me a gentle kiss, rolling off me, and withdrawing his half-hard cock. At that moment I felt empty and separated from this wonderful man. He turned to Julie and said, she's a great fuck. Let me know when I can do her again, and then he stood up and left the room.

"Where is he going, Julie?" I asked as I continued to cry from all the euphoria.

"Oh silly girl, just let those tears out, baby. How did he make you feel?"

"I felt like I was part of him, and that we were one. I felt a closeness I had never known, and I didn't want it to end. Is he coming back?" I asked, hoping to lay with him again.

"No honey, he's done with you. That's what guys do. They love you, and then they are done. But now you know what a girl feels. Right at this moment, the tears you are crying, the feelings you have for that man, and the desire to be with him, is what we girls feel, after blissful sex with our man.

Congratulations, baby, you're now one of us, a real girl with the same feminine feelings. Julie held me and told me everything would be fine. We slept together in each other's arms that night, never again husband and wife, but true girlfriends forever.

CindyTV
CindyTV
1,919 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
10 Comments
AnonymousAnonymous10 months ago

Epilogue: Julie set up more men to fuck her husband who was pretending to be a woman. But all women are eventually jealous or just plain mean to other women who could be a threat. A couple of her boyfriends told her to get lost because they enjoyed "Cindy so much better. So Julie showed her true colors and on the day "Cindy" found out he has serious STD's Julie left him high and dry. She divorced him for being a pervert and he had no evidence that she was involved. She just laughed and laughed at her pathetic ex-husband after taking him to the cleaners in the divorce. She was getting on fine with her life after he died, but his dad put two and two together. One day Julie disappeared and was never heard from again. Unknown to anyone her father-in-law kidnapped her and sold her into sexual slavery. She eventually met the same end as she'd given to her husband. A month before she died she received a brief video from her ex-father-in-law. He was grinning from ear to ear, "Paybacks a bitch huh slut?"

cdCindy1cdCindy1about 1 year ago

FANTASTIC STORY -- MORE THAN 5 STARS.

I truly love love love this story. It is exactly what I want to happen with my wife and a big stud male lover. The detail is fantastic and the whole story really turned me on. There are many excerpts that truly hit home with me and one of them is:

"Cindy, it's time. You're about to become one of us, baby, and there is no going back from this. Once he fucks you and comes inside you, your manhood is gone forever. You are now a cocksucker and in a few minutes, you will be a complete girl, just like me." (spoken by wife)

I truly wish my wife would be like your wife. I truly want to be just her girlfriend and not her husband any more. I know I'm a sissy faggot cocksucking bottom bitch (yes, that's me) and I want her to tell me that I'm no longer a "man" but rather I'm now a "gurl". I only want sex with men; not with women at all -- not my wife, not any woman. Hopefully one day I will have such a talk with my wife and she will be truly happy for me. I hope she will fuck other men while I watch and then she will watch me while those hot studs feed me their cocks and fuck me.

P.S. You will notice that my female name is also "Cindy". You and I do have something in common.

I love your stories. Keep up the great writing.

Hugs & kisses,

cdCindy XOXOXOXOXOXOXOXOXOXOX

AnonymousAnonymousabout 1 year ago

Even crossdressers are allowed to dream.

EroticaReaderEroticaReaderalmost 2 years ago

I absolutely LOVE this story Cindy. Like she had wanted for so long, I also want this. Especially with a loving wife who would encourage me as Julie did. Sadly, for me, that will never happen, but I can imagine it as others who have commented, by reading and imagining.

Thank you so much, honey, for sharing your stories with us.

ER ...

AnonymousAnonymousabout 2 years ago

Such a Delicious story!

I'd 💘 to be treated as a girl & feel wanted & needed for sexual bliss.

Thank You Cindy!

Show More
Share this Story

Similar Stories

The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Becoming Chloe Crossdressing leads to accidental Cuckold with wifey.in Transgender & Crossdressers
Becoming Ashley A man embraces his feminine side when encouraged by his wife.in Transgender & Crossdressers
"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
A Double Date with My Wife My Wife and I Get Fucked Together.in Transgender & Crossdressers
More Stories