This is a true story; If you are not 21 or over do not go any further. If you do not like man on man sex go no further.
...I turned off the lights and climbed into bed with Howard, squeezing my small body against his.
I drifted off to sleep quite easily. I had never slept with anyone before and startled myself a few times by rolling into him or backing into him. His big body didn't move much until he rolled over on his side and pulled me into a spooning position, where we spent much of the night.
Early in the morning - it was still dark outside - I awoke to the feeling of Howard's hand on the flat of my belly. His touch was light, barely perceptible and, with my back to him, I wasn't sure if he was asleep or awake. He moved his hand slowly and I felt his breath on my neck as he pressed his stomach against my back. Slowly his fingertips slipped below my navel, and just under the band of my panties. His palm was now pressed firmly against my body as he pushed it further, finally cupping my cock and balls in one gentle squeeze of his large hand. He started kissing my neck and his squeezing continued and I knew he was awake. I felt my cock starting to respond to his touch and was somehow worried, or at least not sure what to do. I gently placed my hand on his to stop the motion and whispered over my shoulder "That's alright Howard, you don't have to".
He shifted his weight so he was up on an elbow, looking down at me, he kissed my shoulder and whispered back "But I want to baby, you've been so good to me, let me do this for you?"
I nodded my head in agreement and withdrew my hand from his.
He slipped his fingers along the waistband of my panties and told me to help him, so I wiggled and helped slide them off of me.
His free hand ran up my leg and inside my thigh, pulling me to him as he shifted his body partially under me. I felt so small and frail lying against his large body, his arms encircling me in a bear hug, rolling me further atop of him. As I looked up at the ceiling his hands plucked and played with my body, my cock thin and fully erect in his hand. He strongly gripped the shaft and started jacking me, quickly, intensely.
It was too much for me, almost painful and I reflexively drew my knees up to slow it down. With one of my hands slowing his wrist I whispered back to him "Please, not so fast, not so...rough".
He stopped and hugged me and lightly replied "Sure baby, you want it to be soft and easy?" he asked as he slowly resumed a soft stroking of my shaft.
I whimpered my ascension.
"Sure" he said, nibbling my ear "I'll do that for you...let me get something to help".
He slid out from under me and rolled off the bed. I sat up on my elbows to watch him - his thick belly, this broad shoulders, the dark hair that covered most of his body - while he searched through the nightstand. He found a white bottle of lotion and squeezed a large amount out, rubbing his palms together to warm it. The scent of coconut butter reached me as drew near, pulling my body back over his. As he positioned his body beneath me, with one hand I reached back to take hold of his thick cock which was poking through his boxer shorts.
He slowly pulled his hips back, thrusting his stomach forward to to pull us apart. "No, no, no" he whispered, "None of that now, it's time for you to relax".
I let go and brought my hand away, placing it on my hip. He shifted back under me, his left leg trapping my left ankle, his right knee inside my right knee, holding my legs open. His left arm was around me, hugging me, smoothing the lotion onto my nipples and breasts. I closed my eyes and leaned back, enjoying his touch, enjoying the scent, feeling very happy, anticipating more.
The fingers of his right hand were tickling my exposed nuts now, and he rand his finger along the bottom of the shaft, stopping at the head. His whole hand wrapped around my shaft in a warm, slippery fist. His motion was soft and slow, synchronized with the music he was playing on my chest.
He nuzzled his face into my neck, kissing, sucking, whispering.
"You are so hot baby, let me do this for you" He continued "You've been so good to me, draining my nuts - using your hot little bottom, your hands, your mouth to please me, taking my seed into you...I know you need to get off too..."
"Yes baby..." I gasped back
"So you come to me then, come to daddy and let me help you baby, I don't mind...you don't need a girlfriend - making fun of this little cock or your soft body...I can do this for you...we both know that I'm still the man here, right?"
"Yes, yes" I moaned "You're the man...oh that's soo good, soo good."
His grip had relaxed and he simply held his thumb and pointer finger in a ring which he pushed up on down on the head of my cock in very short strokes. I was bucking my hips to push further, but he moved his hand further away, keeping the action limited to the head. His other hand held my nipple and was pinching and pulling.
"Easy baby, not so fast, let me enjoy this a while..." he laughed lightly, teasing my body with his touch.
I held one hand on my belly trying to push back and control my quivering thrusts, my other hand I reached back with and placed on his cheek, gently holding his ear.
He continued playing with my body, bring me to the limit of ejaculating, and slowing down many many times. My heart was racing and my breathing was erratic - I felt like I was running a marathon as he stroked and tickled and pinched and pulled. He whispered hot, dirty things into my ear - all the things he wanted to do to me and have me do for him, as his girl. "My girl, my girl" he chanted. "Yes yes" I moaned.
He tightened his grip around my shaft and pulled me into a tight bearhug as he intensified his stroking. "Do you want to get off now honey?" he cooed in my ear.
"Yes Howard, oh please don't stop"
"Yes, let me love you, let me help you here...let me be your man"
"My man...yes Howard"
"And who's the girl here?
"Me, I'm the girl Howard, you are all man to me babeeee, oh please don't stop"
He held me tightly as my lower body lurched, and lurched, lurched again, spurting my cum with each spasm. My eyes were squinted tightly closed as I reached down and held his hand to help extract the remaining build up of cum.
I laid back against him, never having felt so completely spent and exhausted. He rolled us to the side and pulled the blankets up over us, kissing my cheek and telling me to rest.
I laid there, my eyes closed, head spinning. I had no idea where my cum had landed, I could feel Howard's thick cock against my bottom and knew he was horny, but I was helpless to move. He was propped up on an elbow, looking down at me. I laid there breathing heavy as he smoothed a hand along my shoulder, whispering to me that it was alright. My heavy breathing had turned to sobs, and he held me tightly, planting kisses on my face, neck and shoulder.
"Shhh" he soothed "just rest baby, everything is fine".
I couldn't understand the emotions that were flooding my body and why they were causing me to cry, but it didn't last long and, with his gentle caring I drifted off to sleep.
I awoke sometime later, alone in the bed, the room filled with sunlight.
I heard Howard walking down the hallway so I propped up some pillows and sat up, noticing the smell of coffee and breakfast cooking. Howard stood in the doorway and smile "Oh good, you're up, good morning - how do you feel?"
"Groggy, but wonderful, happy, I had a wonderful...that was, was very nice of you...unexpected...but nice."
He smiled. He looked freshly showered. He was wearing a very heavy terrycloth cotton bathrobe, white with gold piping trim. Over his arm he had a second bathrobe of the same kind, which he placed along the foot of the bed. "I think this will fit you, it's size small...I'm making breakfast if you're ready to come out, or tell me how you like your coffee and I'll bring it to you..."
"No, I'll be right out, I'm just going to jump under the shower for a minute first."
"OK" as he turned to leave he stopped as said "I'm making bacon and eggs - I hope you're not on a diet or anything?"
"No, it smells great, I'll be right out".
As he left I peeled back the sheets to see my body, with patches of dried cum on my stomach and my thighs. I jumped into the shower and quickly washed off using Howard's bar of Dial soap and his store brand shampoo - very different from the deluxe amenities he had selected for 'my' bathroom. So it seemed to me that he had no real interest in girly things for himself, but understood that I did. I thought about how he had tenderly and lovingly gave me pleasure and how that didn't make him anything less of a man than a man who pleases a woman. He was just being attentive...our roles hadn't changed, he had made that clear.
Enough day dreaming. I toweled off and couldn't avoid the fact that my rump had an obvious darkened bruise on it. I looked into the mirror and laughed - my clean towel dried boy-hair was automatically falling into it's side part. I didn't think I should put the wig on with wet hair, and didn't want to have Howard wait much longer so I decided to go out as I was. I wrapped myself into the plush bathrobe and tied the belt around me. I looked down at my feet and considered that wearing the high heels with the bathrobe would look a little over-the-top, but my cute toes with nail polish would look fine on their own.
I walked out to meet Howard in the kitchen and he poured me a mug of coffee. As I fixed my coffee with milk and sugar he made my eggs to order. The kitchen table was set for two and we enjoyed our breakfast together. I was surprisingly hungry and ate every bit of it. As Howard wiped his mouth with his napkin he placed his hand on mine.
"Chris, I want to say 'thank you' to you for letting me touch you like I did last night"
"Thank you Howard, it was, really...nice of you..."
He smiled and cut me off "More coffee?" as he got up and poured himself another cup.
We fixed our coffees and he motioned for me to join him in the living room. We sat on the couch together, sipping our coffees, with his arm around me.
I held my mug with two hands, eying him over the rim. He came away from his mug, looking at me "You know I want you to be happy too Chris..."
I nodded
"...and what we did doesn't change anything. You are beautiful, and sexy, and feminine and you like to please men, you want to please men - men like me and Tommy, maybe others. I'm not wrong am I?"
"No" I rushed "I like doing those things for you...really want to..."
"Good, so you like the taste of cock, the taste of cum, the feeling of a cock in your mouth or in your ass - right?" he was almost laughing, but not quite.
I blushed deep red and nodded and he rubbed my shoulders and neck.
"It's OK" he responded "you are hot and sexy and better than a woman". I looked up into his eyes at that. "Yes - not only do you have a sexy body, you know how to dress up nicely, shake your booty around, and then you stop teasing and let your guy get off - on you, in you, whatever he wants...whatever I want...and that is awesome. Most hot looking women are cock-teases, but you, part of you, is a guy that knows that guys need to get off, frequently, and it means a lot..."
I set my mug down and snuggled my arms around him. He set his mug down and held me.
"So I love you for letting the woman side, the female side of you come out, to please me. I know you like it and I know you need it as much as I need to drain my nuts. It's OK..." he soothed.
He lifted my chin with a finger and looked down into my eyes. "And I also know that part of you, a small part of you," he smiled "is a boy, with a cock that also needs release once in a while. I know that...that you have both needs."
I nodded my understanding. He brushed my hair back and looked at me. "I want to help you with that when you need it, I don't want you feeling like you have to got to someone else, boy or girl, for it. You can share that with me, and it doesn't change anything with us...do you understand?"
"Yes Howard, I, I, didn't know...I was afraid...afraid that I'd insult you or get you mad at me...and...and..."
He held me as a sob caught in my throat. "Shhhh, shhh" he quieted me "...and that's why you were crying...you didn't understand that I wanted you to share that side of you with me, ...that I wanted to help you get off, that you're still like a woman to me...you see...it was just like a woman orgasming, you know?"
I nodded yes and dried my eyes. He held my face in his hands and kissed me, and then kissed my eyes which were wet with new tears. "Thank you Howard, thank you for....understanding me, being nice to me..."
"We can be nice to each other, he said" as he pulled aside his bathrobe to expose his cock which was excited and pulsing with life. With a barely perceptible nudge of his hand, I dropped my head to his lap.
"Yes dear" as I took the head into my mouth. I licked the head and then the shaft and moved my hands in as his spread he legs, freeing his large nutsack. I was now on the floor kneeling and sucking. His moans told me everything I needed to know as I adjusted my pace, pressure and depth. I tasted his precum and after a while he gently held my head back as he slid out of my mouth, moving his body to the side. Hungrily I looked up at him, hoping he'd finish in my mouth.
"Ohh Baby, I need to sink this into you, feel you squirm below me as I pound you - please tell me you want that"
"Yes, please baby, anything..."
He got up and went into the kitchen and came back with a plastic baggie bag and can of vegetable shortening which he set on the floor by me. He roughly shoved the coffee table away, spilling the coffee mugs, splashing coffee all over the white carpet. He quickly grabbed two large pillows from the couch and set them on the floor. I was nervous and scared a little with the frenzied pace things were taking. He motioned to the pillows telling me to lay down as he ripped open the can of shortening and began greasing his cock. His cock was huge, red and veiny and my bottom wasn't lubed. I remember the brutal sex I had with Tommy and was worried as I crawled onto the pillows, Howard's hand on my elbow guiding me. I laid down on the pillows, spreading my legs. Howard lifted my bathrobe up exposing my bare bottom. I looked back to watch him place his hand inside the plastic bag and push it into the can, taking a large scoop of grease. He pushed the grease up into my bottom, forcing two fingers in with a twisting motion. He worked his fingers, pushing the grease into me as ho opened my bottom. He took another scoop of grease and did the same thing. I was sure that my bottom wasn't yet ready for his cock, that two fingers and just a little prep weren't enough, I felt him getting in position behind me, moving my legs, so I quickly said "Howard please, let me..."
"Shhh" he cut me off and was immediately pressing his cockhead against my rosebud. I writhed in pain. He had one hand between my shoulder blades pushing down, the other held my ankle like a wrestling move...he was pinning me with his cock!
I was trying to crawl away from the pain but he pushed and ground his cock deep into my ass with a grunt. He stopped and let me get used to his cock inside of me. Tears stung my eyes and his hand held my face to the carpet as he started withdrawing his cock. Slowly he pushed it back in, the pain rippling through my body, trapped beneath him. I bit my lip to keep from screaming, tears streamed down my face as he continued.
After a few minutes he stopped his assault and took his weight off me, his cock still deep inside my bottom. He stroked my back gently. "I know that hurt baby, but this is like our honeymoon, like our first time having real sex and I needed to loosen you up, we aren't always going to have time to do a lot of foreplay....and I needed to let you know you could take it like this...maybe even enjoy it like this...".
With the pain, my cock and nuts had shrivelled to their smallest state, there was no way I was enjoying this. I'm sure he saw the fear and pain in my eyes as I turned away from him.
"Hey, honey...last night you got what you wanted, what you needed. I'm trying to let you know what I need sometimes. It doesn't have to always be like this, but sometimes I need to get your pussy like this, you need to know that sometimes it has to be this way."
I was propped up on my elbows now, my head hanging down not looking at him. Pain was pulsing in my bottom.
"If you want, I could stop," he offered. "You can get up and leave right now, forget about all this and never come back. Or..."
I looked at him over my shoulder, wide eyed, hurt, sure he knew the pain his ultimatum was giving me.
"Or...you could let me enjoy this hot piece of ass you freely give me, let me plow my cock into you, put my seed into you...you get to decide. Tell me, do you want me to own this body of yours, be your daddy?"
I turned away from him. Tears were falling onto the carpet. I didn't want it to be like this. It was painful and he wasn't very caring. He wasn't usually like this. But he had needs, this is what he wanted and he was letting me know how to please him. He had been nice and cool about a lot of things. He treated me nicely and bought me nice things. He had taught me a lot about sex...was the first man to make me taste his cum. He didn't shun my feminine side, he encouraged it and he even helped get me off last night.
"Baby you have to tell me if this is going to work or not honey, I need to pound the sweet ass you put in front of me. I need a woman baby, not a blow-job queen, so tell me where this is going..."
I turned to look back at him "It just hurts, that's all"
I lowered my torso and laid my face down on my hands.
"That's a girl, my girl...my little Christine...giving up her booty for her man" he taunted.
I squinted my eyes shut as he resumed thrusting his cock in and out of my bottom. Each thrust seemed more painful than then one before it and I cried unashamedly. My tears had no effect on him, maybe they were even a turn on for him. After a few minutes he pulled my bottom up so I was up higher on my knees, his hands on my hips and he started thrusting quickly, wildly, jabbing and pulling me against him. I knew he was close to cumming, yearning for him to finish. He lifted my torso up so I was now squatting back on his cock. He had my arms trapped in a bear hug as he thrust up into my bottom. We adjusted our rhythm so I was moving down as he move up, I noticed my cock was thickening, not fully erect, but responding positively to the sex. He stopped thrusting an told me to 'work for it'.
Sensing what he meant, I used my leg muscles to lift myself and lower myself against him, impaling myself on his cock. He laughed and whispered nasty things in my ear. My cock was becoming erect and he started thrusting up into me, slamming three huge thrusts, draining his balls and filling my bottom with his cum. My cum spurted out, and he freed my arms and took my hand, instructing my to grab my small cock and finish jerking it, while he finished in my bottom.
When he was done, he pushed me forward and slid his cock out of me. My bottom was burning, even without his cock in me. I felt back and felt his goo, and a very loose bottom hole. My mind exploded and I thought about bleeding, stitches, incontinence. New tears came as I sat there. Howard stood and gathered his robe about himself. As he walked down the hallway he said he was going to shower and that he had tickets to a play if I wanted to join him.
As I scurried off to the my bathroom, I knew that I was going to get dressed, get out of there before he was done showering, and that I'd try like hello never to see him again.
End Part 12