50514 Stories
538711 Comments
Create account

New Stories 50514

Fiction 23890

Blowjob 12200

Consensual Sex 9729

Anal 9581

Fantasy 9122

True Story 9036

Incest 5838

Cum Swallowing 5426

Dark Fantasy 5112

Male / Female 4974

BDSM 4244

First Time 3685

Bi-sexual 3590

Teen 2963

Cheating 2794

Erotica 2539

Lesbian 2477

Domination/submission 2470

Gay 2331

Ass to mouth 2210

Oral Sex 1956

Romance 1795

Authoritarian 1770

Bestiality 1764

Exhibitionism 1761

Group Sex 1706

Fantastic 1611

Masturbation 1560

Female solo 1547

Hardcore 1443

Boy 1310

Coercion 1260

Black 1253

Cruelty 1195

Blackmail 1194

Diary 1166

Asian 1157

Humiliation 985

Body modification 839

Job/Place-of-work 832

Young 815

Interracial 793

Female Domination 792

Rape 750

Discipline 670

Sex Joke 667

Drug 642

Mature 620

Non-consensual sex 616

School 587

Death 578

Non-Erotic 562

Written by women 536

Extreme 523

Cuckold 499

Threesome 457

Virginity 456

Reluctance 454

Poem 425

Wife 398

Mind Control 398

Voyeurism 390

Pregnant 330

Male Domination 320

Violence 265

Spanking 220

Fisting 204

Foot or shoe fetish 200

Prostitution 185

Transsexual 184

Monster 181

Slavery 161

Lactation 153

Toys 148

Gothic 145

Murder 138

massage 134

Latina 128

Water Sports/Pissing 125

Enema 100

Torture 86

Stories in DB: 50514
Comments: 538711

Part 4

Categories True Story, Anal, Gay, Cum Swallowing

Authror: pantieboy1985

Published: 23 February 2018

  • Font:

Not to long after that fateful week with Frank 9/11 happened.

Frank joined the army and I missed him terribly.

Jennifer would let me know how he was doing but it still didn't help.

One day Jennifer came by. It was a teacher planing day so no school. Grandma was at work and I was in my usual outfit as Sarah.

"Do you want to go shopping ?" Jen asked.

"You know it", I said excitedly .

I grabbed a bag with my boy clothes just in case we went back before my grandma got home then hopped in the car.

On the way to the mall she told me Frank wrote me a letter.

Excited I opened the letter, it was addressed to Sarah. He always knew how to make me smile. He went on to tell me how he was doing and that he was safe and working in the motor pool, and was planing on going to school for aviation mechanics. At the end of the letter he told me that he loved and missed me.

With tearfilled eyes I folded the letter and put it in my bag. I decided to write him back latter.

When we arrived at the mall we did the usual thing. Manicures, pedicures walking around checking out boys.

I spotted my old friend Mike (really my only friend out side of Frank and Jen) over talking with some boys from school. We grew up togeather, always in the same class since kindergarten. Then last year he moved to a different school district so I don't get to see him often. But we had planned on a sleepover for the weekend.

Mike had no idea about what had happened to me over the last few months and knowing how he was I had know intention of telling him.

Then I herd a whistle when I looked it was Mike.

"Why don't you go talk to him?" Jen asked

"I can't, he might recognise me I said".

"The real Sarah didn't." She replied

"Sarah and I went friends " i protested.

"He wont, now go chicken". Jen teased.

I walked over to Mike. Palms sweety and heart racing. I was completely scared he would recognise me and freak out.

"Hay beautiful" Mike said, "What's your name?"

"Sarah" I replied.

We talked for a few minutes the he said "you look real familiar".

My heart almost stopped.

"No, I don't think so", I replied "I'm not from around here."

We talked for a few more minutes the I went back to we're Jen was waiting.

"Oh my God, my heart is still racing " I said

Jen laughed then said "let's get back to shopping."

We went in a few stores and I found a rally pretty pair of bubble gum pink string bikini panties and matching bra.

When I got home I hid my new clothes in my hissing spot. A loose panel in my closet .

The next morning was Saturday and Mike would be there soon. I got up and ate breakfast then went to my room to get dressed. Since grandma was home and Mike was coming over I had to dress as a boy. But I had a new pair of panties I was dying to try on. I decided that they wouldn't know so I pulled out my new panties and put them on. I looked at myself in the mirror and loved the way I looked. The shiny pink fabric, and the string bikini cut made my hips and but looked great. I thought about how Frank would react seeing me in them. I finished getting dressed in black gym shorts and a white t shirt.

Mike arrived and the day went by uneventful. We were in the garage which was our usual hang out. Goffin around listening to music then we started wresrling.

During the match my shorts slipped down reveling my panties.

"What the hell dude, your wearing panties!" Mike said

"Why are you wearing them? When did you start? Are you gay?"

Mike was asking question so fast I had no time to answer.

I stood there speechless in total shock on the verge of crying when Mike noticed.

"Dude don't worry I'm not gonna tell you just suprised me. Relax, ok" Mike said.

After I called down I told Mike about Frank and I and how I pretend to be Sarah at the mall.

"Wow, that was you?" He said surprised.

"I just can't believe this, so you wear girls clothes and you had sex with a boy?" He questioned

"Yes" I replied

" So you actually let him stick his thing in your butt! Didn't it hurt" he asked

I replied " a little at first but after a while it started feeling really good."

"So you actually like it, I mean dressing as a girl and having sex with boys?" He asked

"Yes I do" I answered

We continued to talk for a while the Mike asked "Can I see your panties? I've never seen any one in them before, girl or boy."

I stood up and pulled down my shorts then lifted my shirt. Mikes eyes widened as he took in the view. I spun around slowly the stoped facing him.

"Wow, you actually look like a girl" he exclaimed

"Can I touch them?" Mike asked

I shrugged my shoulders and Mike slowly reached his hand out. He was clearly nervous. His hands were shaking. His fingers touched the fabric just above my tucked member.

He continued running his hand across the fabric then around my hips to my butt.

His touch felt great.

I had never thought of Mike in a sexual since before that moment. But with his hand rubbing my panty clad backside I couldn't help but notice just how cute he was.

Mike was about 6 inches taller then me, athletically built, he was half Mexican half white so he had a nice skin tone that just highlighted his features.

I found my self getting more and more aroused and looking at Mike' s lap i could tell he was to.

"You know, if you want to fuck me you can" I said.

Mike quickly removed his hand saying " No, I ain't gay dude. i just, I mean you,".

Mike was stuttering really bad something he only dose when he's nervous.

I sat down beside him and said "Frank ain't gay eather. He only has sex with me because I look like a girl. And if you think about it, I look like a girl, dress like a girl act like a girl so you would be fucking a girl with a few boy parts".

"But i can't , my mom would kill me if she ever found out." Mike said

"Ill never tell" I replied.

I could tell Mike was on the fence so I decided to make the first move.

I move in front of him and put a leg on each side then straddled him.

Mike was speechless but made no effort to stop me. I started to grind my self on his sick which he seemed to enjoy. Then I leaned in and kissed him.

Then Mike gave in and started making out with me while I grinded on him. I reached down and started undoing his buckle then freeing his cock.

Mike continued kissing me and rubbing his hands across my butt.

I reached behind me and pulled my panties to the side then put some spit in my hand and rubbed it on his member.

I then raised up and placed the head at my entrance and slowly lowered my self down. I still haven't seen his cock but it felt big and so nice penetrating my little hole.

After a minute or two I could feel his pubes against me. I then sat down the rest of they way forcing as much of him inside me as I could.

Mike started letting out soft moans as I started to raise and lower on his shaft.

Feeling his member inside of me stretching me out put me in a state of complete bliss. I started bouncing up and down fucking my self with his cock while kissing him. Precum was leaking out of me like a fountain.

Mike said " I am about to cum".

" cum inside of me" I replied

And with that his body tended up, I slammed down as hard as I could and he unloaded shooting shot after shot of hot gum deep inside of me.

We stayed like that while we both caught our breath .

I could feel his cock getting soft inside of me.

" wow, I can't believe I just tucked my best friend in the ass!" Mike said.

"Well, did you enjoy it?" I asked knowing the anwser.

"Oh yeah." Came his reply.

I herd my grandma yell out the back door " dinner is ready"

We both straightened our clothes and went in to eat.

We sat down at the table and I could tell Mike was nervous. Me, I was concentrating on keeping his cum inside me but eventually had to go to the bathroom.

About midway through the meal my grandma looked at Mike and asked " are you feeling ok. You're really quiet."

"I'm fine ", Mike replied, " I just have a lot on my mind with school and stuff." Obviously lying.

I knew he was concerned about what had happened, and being caught.

After dinner we went to my room and talked.

" I still can't believe what we done" says Mike. "Don't get me wrong", he continued "But I just can't wrap my head around it. I mean my best friend dresses like a girl wich is fine I'm cool with that but why am I so turned on. I'm not gay! Am I?"

I replied, " No, just because we had sex doesn't mean your gay. You were attracted to my girlish looks not my boy features. And like I said before since I want to be a girl and look like one you technically had sex with a girl."

"But your a boy", he protested.

We continued back and forth for a while, then I said "look just because we had sex didn't mean we have to be boy friend and girl friend. We could still be friends just one that your able to fuck when you want."

Mike sat in silence while we watched a movie. Then my grandma knocked on the door saying "it's time to get ready for bed.

I got up and went and took a shower. While in the shower I couldn't help but think of Mike's cock. I knew it was big but i haven' t seen it. I wentered what it looked like. What it tasted like. I continued showering then shaved my legs and returned to my room.

Mike went for his shower next.

While he was in the shower I decided I was going to surprise him and dress up. It was high risk because I never wear more than panties when my grandma was home. But I figured it was almost bed time and I could wear my pjs to cover up until she went to bed. With that decided I put on my pink Barbie panties with matching training bra, white thigh high stockings, a red plaid skirt and white top. Then my pjs.

Mike came in the room after his shower and seemed more upbeat. I guess he had time to wrap his head around things.

We started playing play station then he stoped and turned to me and said, "after I thought about it a while I'm glad we had sex. It felt really good, and I really don't care that you have boy parts. To me your a pretty girl."

"Thanks", i replied.

"I just feel bad that you didn't get off." Said Mike. "If you would like,I guess i could jack you off."

"No, I prefer to gum with my butt," I replied.

Seeing the puzeld look on his face I explained, "when a boy is fucking me the feeling of him sliding in and out makes me cum. I always gum harder that way the I do by jackin."

"But you didn't cum earlier" he said.

"I was close but you came before me"

"Oh, I'm sorry" he sheepishly replied.

"That's ok. You'll have plenty of opportunities to make it up to me". I said while leaning over and kissing him.

We started making out . I placed my hand on his already rock hard cock. I pulled his cock through the opening in his pajamas and could here him start to breath hard as I stroked him.

What about your grandma " he whispered.

"Don't worry, I'm just gonna suck it. We will wait tell she gose to bed before we do anything else."

With that I looked down seeing his magnificent member for the first time.

He was every bit of seven inches and thick. I could barely wrap my hand around it.

I went down and kissed the tip then started running my tongue around it before putting him in my mouth. There was a little bit of pre cum wich I greedily licked up. Then I wrapped my lips around the head and started to suck him in. In this position I could only get about four inches in before his cock was touching the back of my throat. I held him there and started rotating my head around then started to pull back keeping the light suction. His cock tasted so good. I could feel his hand go onto my head and he leaned back. I would suck him the pull him out and lick the head while catching my breath. Then tack him back in. His cock started to swell and his breathing more shallow. I knew he was close so I sucked as hard as I could then reached down and rubbed his balls. His body tenced up the he unloaded shot after shot of hot cum into my mouth. His cum taste different than Frank's. It had sort of a sweet flavor. Must be all the juice he drinks. I held him in my mouth swallowing every drop he had to give, then slowly I raised my head and stop when only the tip was left in. I locked around the tip then with a pop pulled his cock out of my mouth.

"Holy crap, that was incredible! Did you actually swallow my cum?"

I noded and grined a little then put his deflating cock back in his pajamas.

About tthat time I heard my grandma say "What are you boys doing as she opened the door".

"We're just playing play station" I replied.

"Oh, ok. Well I'm going to bed you boys keep it down and don't stay up to late."

"Ok, good night",we both replied.

"Oh my God, we almost got caught", Mike whispered.

I let out a little giggle then we returned our attention to the game that had been on pause.

Once I was sure my grandma was asleep I stood up and removed my pjs to reveal my outfit.

Mike's eyes got wide and his mouth dropped.

I stood before him and gave a little twirl. "Do you like what you see?"

A node yes was all he could do as he sat there taking in the view.

Then Mike stood up and walked to me. He wrapped his hands around me placing one on my back and the other on my butt.

Pulling me close and kissing me.

We stood their kissing while Mike's hands romed my body. His touch sending shivers up Mike spine.

Mike pulled my top off and rubbed my chest through my bra and the other hand made it's way under my skirt and started rubbing and squeezing my ass.

Mike picked me up and carried me to the bed gently laying me down. He then stood up and removed his pajamas and underwear. Standing before me completely naked. Oh, he was so hot. His body was absolutely amazing.

He then reached down and unzipped my skirt and slowly removed it, leaving me in nothing but my Barbie panties and bra.

He then started kissing his way from my feet up my leg. I spread my legs as he kissed my panty covered cock. Then my belly and worked hid way up to my lips.

I wrapped my legs around him as he grinds his cock into me. His tongue massaging my tongue. His hand rubbing my nipples through the thin fabric of my bra. Then he sat up and rubbed both hands across my chest, down my belly to the waist band of my panties. Slowly he started pulling them off freeing my little cock from it's tightly tucked position. Looking down at me he spread my legs wide rubbing his hands up my thigh to my hips. He brought one hand to his mouth and spit in it then rubbed his spit into my eagerly awaiting hole. His finger moving in a circular motion and pushing in slightly. He the spit in his hand again and rubbed it over his cock.

I pulled my legs up as he lined the head of his cock against my entrance then he lowerd himself down and kissed me while he slowly pushed in. I could feel his cock spreading my hole little by little filling me up. Once his hips were against mine he rocked them pushing him self completely in me. I reached down placing my hand on his butt and the other around the back of his shoulder continuing to kiss as he started moving in and out.

"Oh my God, your cock falls so good" I whispered in his ear.

Kissing my neck then Mike replied " you are so hot and your ass is amazing."

He continued kissing my neck while slowly fucking me. With every thrust in he would rock his hips to get every inch of his cock in me.

With all the buildup from earlier I felt my self on the verge of orgasm in no time.

Squeezing his butt holding him inside of me as my orgasm hit. My body tenced up, my back arched and my ass spasming on his cock.

As I started to come down from my orgasm I grabbed the back of his head and stuck my tongue as far I'm his mouth as I could. He started to trust into me again.

A few minutes latter I told him to lay down. I then climbed on top and lowerred myself down on his cock. I started bouncing up and down and rotating my hips fucking myself with his cock.

Mike reached his hands up and started rubbing my nipples then he sat up and removed my bra. Then started licking my nipples. His hand lowered down and grabbing my butt guiding me as I rode his cock.

He wispered " I want to fuck you from behind".

I climbed off him then bent over resting my chest and head on the bed with my ass up in the air.

Mike kissed the small of my back then put he cock back in me.

He felt so much bigger in this position. His cock rubbing across my prostate with every thrust.

I could feel another orgasm building quickly. Then Mike pushed in deep and could feel his cock jumping inside me putting me over the edge causing another orgasm to rip through my body.

As our orgasms ended I rose up with his cock still in me. He wrapedd his arms around me. I turned my head and kissed him grinding my ass into him while I felt his cock slowly start to go soft until he slipped out.

We both lay down and drift off to sleep with him holding me and his cock he nessaled between my checks.

Views: 3868     Rated: +8.92

Add to favorites
  • Abuse on a story

    * Required field
Comments (1)
Unknown user — 28 February 2018 20:22
This was a awesome story. I have had several sexual encounters with friends like this over the years. Or was always awesome.
  • Comment story

    * Required field