Grace was a shy young thing that worked a couple of doors down from me. She had been hurt pretty bad by an asshole guy or two along the way and it took me several months and a dozen dates to finally get her to trust me. That first night in bed I found a tiger in a slightly overweight kitten suit.
She was not fat. She had a nice shape and breasts that would make babies cry a block away.
She was not a super model either, but then again who wants to be stabbed and bruised while making love. Grace was soft, comfortable, and very passive aggressive. She loved to make love in any way, shape, or form.
With her under you, you had to hold on and you got as good as you gave. From behind, she was passive with her big round soft butt stuck up high and she loved to be fucked long and hard. She would moan, whimper, and yell, “Harder, harder.”
When she rode you cowgirl, she put you away wet, tired, and drained. She loved to have her big breasts massaged firmly and her nipples pinched roughly as she bounced up and down and then ground her clit against you. Orgasms were not a problem; she had dozens on a good night.
Our relationship grew enough for her to invite me back to her place. A little while later, she introduced her toys and I found out her passion for anal sex. She loved it, whether I was fucking her pussy and had a toy jammed up her ass or the other way around. She seemed to come twice as hard, which was saying a lot.
I bought her a slender double-ended soft latex dildo, among other things, for her birthday. That night after a few drinks and dinner, we ended back at her place and I fucked her with it. Actually, I folded it, inserted half in her pussy and the other half in her ass. I fucked her hard with it while I ate her sweet juicy pussy.
We were in a sixty-nine and she swallowed my dick whole. Up until then oral had been mostly on my part and haphazard on hers. Now she was gobbling on me like there was no tomorrow and she couldn’t get enough of my dick in her mouth. In the end, she came, I came, we came, and holy shit, what orgasms.
Now the rest of the story can be told.
I’m an open-minded dirty old man and always have been. In my youth I was just working on the age, I had the rest down pat early on. As for sexuality, I am about as straight as you can get, not homophobic but straight.
Men have never been anything I ever considered seriously. If I wanted a dick to play with, I had my own, thank you very much. If that is your bend then more power to you. I wish you all the luck in the world and happiness also.
So how does a straight guy end up being fucked in the ass by his girlfriend? Here is how it happened.
Shortly after her birthday, I had to go out of town on business for a few days. We talked on the phone at least once a day, twice on a lot of them. The first few days, all she could talk about were the mind-blowing orgasms from the new toy and how it wasn’t the same without me there.
My first night back home, she greeted me at the door in this little translucent nightgown and nothing else. We ended up have sex right there on the living room floor. Grace fell asleep cuddled up to me.
Sometime during the night, we woke up and moved to the bedroom. I ended up cuddling her from behind. My semi hard dick nestled between her soft warm butt cheeks. It wasn’t long before her hips were moving and my hips were moving. This was an erotic dry hump of the top class.
She would whimper softly as I rubbed my dick against her anus and I would groan softly as she clamped her ass cheeks tightly around my manhood. It was not long before she was whispering, “Please,” in a lust filled pleading voice. I knew what she wanted and I wanted it too.
I wiggled down and slowly entered her hot slippery depths. She sighed and moved her upper body forward, pushing her ass back against me tighter. “Oh, yes. That feels so good but….”
I chuckled and flexed my hips slowly, my dick sliding in and out of her pussy easily. “I know what you want, you want my dick up your tight hot ass.”
“Oh yes, please,” she groaned, pressing back each time my hips went forward. “I love the feel of your big hot dick in my ass,” she added as a strong heavy shiver ran up and down her body.
I slipped my dick out of her pussy and rubbed it up and down in the crack of her ass. She whimpered loudly and pushed back even harder, trying to get my dick in her ass. I slipped it back in her pussy and fucked her slowly.
“You’re teasing me,” she whispered and then giggled as I rubbed my slippery dick up and down in the cleft of her ass.
I slid my dick back into her pussy and whispered, “I’m teasing myself also. I love fucking your ass almost as much as you love for me to. Your sweet pussy is hot and tight but your ass is even hotter and tighter.”
Grace moaned loudly at my words, her ass quivering and fluttery back against me. “Reach over and get your new toy.” I told her. “I want it in your pussy while I fuck your ass.”
Her upper body moved forward, which pushed her ass out more. Her upper knee moved forward, spreading her thighs wider and spreading the cheeks of her ass. I pulled my hips back, lined the head of my dick up with the pucker of her anus, and pressed forward gently.
The slippery head compressed and popped through the ring of muscles tightly guarding her rear. We both moaned as my dick slid home several inches. This was a new position for us. Usually, she was on her knees with her ass high up in the air. I held onto her with one hand on her hip and the other on her shoulder.
Grace gasped loudly at the surprise attack and then moaned long and loud as her hips flexed and jerked against my manhood. I was slowly sliding deeper as she did. In this position, she had more control than anytime else in her life.
She could fuck herself, as she liked, how she liked, and as fast or slow, as she liked. I just hung on and let her have her way until my hips pressed tightly to her ass cheeks. I held her, caressed her breasts as her hips slowed, and finally quit moving.
“Did you get your toy?” I asked.
She giggled and then shivered. “How am I to remember what I was going to do with that hot dick of yours slowly sliding up my ass. I’m doing good to remember my own name.”
She moved her shoulders forward more, leaned slightly, and felt over the side of the bed. A moment later, she pulled her toy and the towel it was wrapped in from under her mattress. Her leaning forward and then back moved my dick in her ass, which made her inner muscles clamp down firmly on me.
Her hips were twitching and jerking as she unwrapped her toy. “I love this position. It’s so comfortable and lets me move in ways I’ve never been able to,” she whispered as she flexed her hips, moving her ass back and forth along my shaft.
She moaned and then whimpered as I used my hand, leg and foot, to get her knee raised and her thighs spread. She did not need any coaxing past my spreading her legs. A few seconds later, the double-ended toy was sliding easily into her pussy. I could feel it sliding against my shaft through the thin membrane separation her pussy from her anus.
Her hips jerked and twitched harder as the toy went in and then she sighed as it stopped moving. It was in deeper than the head of my dick. I flexed my hips and reached across her thigh to take the dildo from her.
“Now, just relax and leave the driving to me,” I whispered.
I kissed and bit the back of her shoulder as I moved the dildo slowly out and then back in and I flexed my hips, moving my dick in her ass. She groaned loudly and shivered.
“I’m…. I’m going to come quickly,” she said with a loud moan.
“That’s all right, I’m in no hurry.” I told her as I fucked her pussy and ass at the same time. The shiver turned to shaking and then her ass clamped down tightly on my dick as she came with a soft yell. Her hips jerked and twitched as I continued to fuck her.
This went on for almost an hour with her having half a dozen orgasms before she rolled over on her belly, pushed her ass up and yelled, “Fuck me! Fuck me hard!”
I had followed her over and was only too happy to oblige. The dildo was still in her pussy and trapped by her thighs. I could feel the ridges on it as I pounded away in her ass. The harder I spanked her ass with my hips, the higher it rose and the louder she yelled.
By the time I came with a gush, she was already working on her third orgasm in a row. I planted my dick as deep as it would go and held onto her hips. I was lightheaded and trembling as she slowly settled back to the bed. I lay on top of her gasping for breath.
I woke up slowly at the sound of Grace’s voice. I was tucked up tightly behind her and was astonished to find my dick was still in her ass. It was only semi hard but…. Grace had the phone up to her ear, and was talking to someone from where she worked.
“I know we’re busy dear but I need to take a sick day.” She paused to listen and then said, “Uh, how can I put this delicately.” She paused a second and the added, “Let’s just say I have an anal problem. It’s plugged up at the moment but I don’t expect that to last for long.”
I could feel Grace’s body move as she repressed a giggling laugh. She listened for a moment and then replied, “Yes, if I get to feeling better, I’ll give you a call.”
She hung up the phone a few seconds later and wiggled her hips. “I wasn’t lying, was I?” She asked and then she did giggle.
I kissed her back and licked the back of her neck. She shivered and squirmed back tighter to me. The back of her neck was almost as sensitive as the outer lips of her pussy. I licked it again and she whimpered softly.
“If you keep that up, you’re going to have to fuck me again,” she whispered. Her asshole clenched and grabbed at my hardening dick. “Oh God, I can feel you getting bigger.”
“It’s your fault,” I whispered back as I clenched my ass cheeks and caused my dick to twitch.
She moaned and pushed back against me, moving my hardening dick in her ass. She whimpered and moaned again. “That feels so good.” A moment later she asked, “Have you ever had anything in your ass?”
I kissed the back of her neck and nibbled on it as I thought the question over. “Yeah, a finger a couple of times and a tongue once,” I whispered in her ear before I nibbled on her earlobe.
“Nothing bigger?” she asked with a soft moan tagged onto the end as I flexed my hips slightly.
I grinned at her question and replied, “An old aluminum cigar tube once a long time ago while I was masturbating and one of my ex wife’s dildos after we split up. She left it and I tried it.”
Grace groaned and shivered deeply several times as I talked. A few seconds after I shut up, she whispered, “Fuck my ass. Fuck it hard.”
I was only too wiling to comply. I pushed on her upper body until she moved forward. Her knees curled up toward her chest and I could now fuck her ass as if we were on our knees but we were on our sides.
She could not move too well but I could raise my hip slightly and spanked her ass, hard and fast. She rotated her upper body even more and chanted, “Fuck me, fuck me, fuck me,” over and over again.
My left hand slipped between her thighs and I lifted on her top leg. She raised the leg and the chant got louder as my dick now went deeper into her ass. Her hand snaked down between her thighs and strummed on her clit, which added volume to her litany. Her ass was growing hotter and kept grabbing at my dick.
It took her longer to come that morning but she was almost howling by the time she did. I was not far behind her and that added to her orgasm as her ass tried to crush me. We lay there in a sweaty exhausted tangle as my dick slowly softened and slipped out of her ass.
She shivered hard when it did and then sighed deeply. “Oh my God, I’m going to sleep for a week,” she whispered and then giggled. “I need to run to the bathroom. There’s a river flowing out of my ass.”
“I had a cork in it but you crushed and melted it,” I joked.
She giggled and nodded. “I sure did and I plan on doing it many more times in the future.”
I groaned and then chuckled. “Ain’t that just my bad luck?”
Grace laughed and rolled over to the side of the bed and got up. She squeezed her thighs together and walked with just her lower legs toward the bathroom. “Oh God, there’s two rivers, so I can’t blame it all on you” she said as she went through the bathroom door.
I heard her giggle when she sat down on the commode. “This is going to take a bath at the very least to clean up. Why don’t you grab a shower and then I’ll get in the tub.”
I groaned as I rolled over and got off the bed. I felt lightheaded as I stood up. “No rest for the weary.” I muttered as I headed to join her in the bathroom.
“No rest for the wicked either,” she said with a grin as I came through the door.
I grinned back and kissed her softly on the lips. As I straightened up I asked, “Are you talking about me, you, or us?”
“You’re the dirty man who likes to fuck my ass and to make me come so hard.”
“And you’re the dirty girl who likes her ass fucked until she passes out from coming so hard.”
We both laughed and Grace whispered, “Then it’s both of us.”
I was cat napping on the bed after my shower as Grace took her bath. I had washed her double-ended toy and dried it before I laid down. Now my mind was going back over the events of last night and this morning. The conversation about my ass came back to me and I grinned as an idea formed in the back of my mind.
A little while later Grace came in and crawled into bed with me. She snuggled up and sighed deeply. “This is so good,” she whispered as she kissed my neck. “I think I need a short nap, how about you?”
I nodded and whispered, “That sounds good and then I’ve got an idea I’d like to try out.”
“What idea?” She asked and then yawned.
“After our nap,” I whispered as I turned slightly toward her and put my arm around her. I kissed her ear and joined her in dreamland.
When I woke up, Grace wasn’t in bed. I smelled bacon frying and rolled to the side of the bed. I found her in the kitchen wearing nothing but a bibbed apron. She gave a little jump as I eased up behind her and slipped a hand in each side of the apron to squeeze and massage her breasts.
As I nuzzled and kissed the back of her neck she shivered and said, “I was hungry and figured you would be also.”
I kissed her neck and licked it, “I’m always hungry around you, and food sounds good too.”
She giggled and rolled her head to the side as I kissed the junction of her neck and shoulder. She shivered and whispered, “Go get some coffee before I throw you on the floor and the bacon gets burnt.”
“Your bacon or the stuff in the pan?” I asked with a grin.
“Yes,” she answered with a giggle.
I kissed the base of her neck once more and released her with a sigh. As I turned to the coffee pot I said, “I’ll see if I can’t burn your bacon a little later.”
“Promises, promises,” she whispered and then added, “You’ve already burnt my bacon at least twice in the last twelve hours. We might have to give it a rest.”
“Then maybe I’ll let you burn my bacon,” I said with a grin.
Grace was stirring the eggs into the skillet and only glanced at me with a confused look on her face.
After breakfast and the kitchen was cleaned up, we were back in Grace’s bed cuddling. I was on my back and she was on her side with her head on my shoulder. My left hand was caressing and stroking her back as she sighed and slipped her right knee over and between my legs. I could feel the heat from her sex against my thigh.
Her right hand was on my chest and caressing it lazily. After a while she sighed again and whispered, “This feels so good.”
I nodded in a lazy sort of way. “Yes, it sure does.”
A couple of minutes later, her hand wandered down across my stomach to find my hard dick. She wrapped her fingers around it and gave it a light squeeze. “I love touching your dick,” she whispered. “It’s so warm and hard.”
She held my dick and ever so often, she would give it another squeeze. After a while, she giggled and then wiggled her hips. “I’m getting horny again,” she whispered and wiggled her hips again.
I chuckled and whispered, “And this is different how?”
She laughed softly, lifted her head, rolled more over on top of me, and kissed me lightly on the lips. She held onto my dick as she did. “I want you in my ass again but it’s a little tender.”
“Do you have any lube and maybe a couple of pieces of soft cord?” I asked as my idea from earlier came back.
Grace looked at me funny and nodded. “Yeah, there’s a bottle of lube in my nightstand drawer and there are some waistband cords in the other bedroom that I took out of some old shorts I threw away.”
I grinned up at her and said, “You get the cords, and I’ll get the rest of the stuff we’ll need.”
“For what?” She asked.
With another grin, I whispered, “You’ll find out.”
When Grace returned with the cords, I had the lube and her double ended toy on the bed. I took the cords from her and handed her the toy. She held it while I applied a little lube to the end. “I really don’t need that,” she whispered.
“Maybe, maybe not,” I said as I squatted down and took the toy from her.
“Put your foot up on the bed and hold onto me for balance,” I told her.
She did as I said, and then giggled as I rubbed the slick head of the toy against her sex and slowly pushed it into her vagina. I kept feeding the toy in until she rose up on her toes slightly. I pulled it out an inch or so and then tied a double half hitch around the toy, close to her sex.
I had her put her foot back on the floor as I ran the cords between her legs and then one each around her thighs to tie the free ends to the dildo just below the half hitches. Grace had a funny look on her face as I looked up at her.
With the second cord, I tied a double half hitch as close to the first one as I could. This time, I brought the ends of the cord up and around her hips on each side to tie them tightly at her tailbone.
When I moved back and looked up, Grace had her mouth hanging open as she wiggled her hips from side to side. The soft dildo swayed back and forth and she giggled. “Now I have a dick,” she whispered. “I can’t feel the outside part but I can sure feel the inside.”
Grinning, I stood up, pressed my hard dick down, and bumped it back and forth against the dildo. Grace giggled, looked down, and fenced with me for a moment by wiggling her hips. Looking back up at my eyes, she asked, “Now what?”
“Now comes the tricky part and maybe the fun part for both of us. The jury is still out on me.”
Grace looked confused for a moment and then I crawled up on the bed and assumed her normal position on my knees with my ass up in the air. Her eyes got big and she shook her head. “I… I… I couldn’t,” she protested.
I pushed up on my hands and then sat back on my heels. I picked up the bottle of lube and crooked my finger at her. “Come here little girl, this won’t hurt you one bit and if you are gentle and use this lube, it shouldn’t hurt me either.”
“I… uh… I….” She stammered but she climbed up on the bed. When she was on her knees next to me, she shivered and whimpered. “This homemade dick you made for me, makes me feel funny inside as I move. It feels good, just funny as the toy moves inside by itself.”
“You should feel what a real dick feels like when I move. It’s kind of weird at times also.” I told her as I handed her the lube bottle.
“I’m still not sure about this,” she whispered as she took the bottle.
I looked at her and grinned. “I’m not either but I have trust and faith in you just like you have trust and faith in me.”
She looked thoughtful for a moment and then said, “You know, that’s very true, I do have trust and faith in you. It’s been a long time since that happened, if ever for that matter.” She looked at the lube and then back at me. “I don’t want to hurt you.”
“Now you know how I felt the first time I fucked your ass. Only in my case there hasn’t been a toy in there in a very long time,” I said as I went back down on my hands and assumed the position she liked so much.
“Uh, what do I do? I have no idea from this side of the dick.”
I grinned at her and shrugged. “Don’t look at me, I’m just the semi virgin waiting patiently. I’m all tensed up, so I would suggest relaxing me first and use plenty of lube. What do you remember about your first time?”
She shivered and looked frightened for a second. “I… uh… it….” She started to say and then stopped. She took a deep breath and shook her head slowly. “It was more rape than anything. Back then I didn’t have a clue. All I knew was that his finger and tongue in there felt really good. When he did fuck my ass, it was hard and brutal.”
“I’m very sorry to hear that and I’m surprised you like it as much as you do now,” I whispered.
She smiled and then giggled. “It was a long time ago and I kept playing back there when I masturbated and it always felt good. The next guy that tried it was slow and gentle. I was very hesitant but he worked magic and I came my brains out. I was cured or was that hooked. In either case, I got over it quickly and then you came along.”
With a hard shiver, she looked at my upturned ass. “I have fantasized about this but never thought it would ever happen. Anyway, I’m far too shy to ever ask and most men…. Well, I always figured they wouldn’t like it.”
“Do you know what and where the prostate is?” I asked.
She nodded. “Yeah, it’s a gland in a mans ass.”
“Did you know that it is very similar in some ways to your g-spot? If it is stimulated and or massaged, it can make for a much stronger orgasm.”
“I didn’t know that,” she whispered.
“It’s an old trick from years ago. Prostitutes used it to get their clients off harder and quicker. More time to turn tricks and more repeat business, it was a win, win situation for them.”
Grace giggled. “I learn something new every day.”
I chuckled and whispered, “Then it is time to take care of your semi virgin.”
She shivered and moved around behind me. Her hand caressed my ass and then she had both hands on my ass. “Your ass is so hard and muscular. A little hairy also,” she said with a giggle.
I wiggled my butt like she normally did and she dropped a hand down to caress and gently squeeze my balls. Her hand moved farther between my legs and she stroked my dick. I heard her whimper softly as she leaned forward and licked the crack of my ass.
A moment later, I heard her whisper, “I’ve never…” and then her hot tongue touched my asshole. I gave a little involuntary jerk and groaned softly as she licked me repeatedly. I heard her moan and the tip of her tongue probed my butt. I relaxed and let her have her way.
I’d had my ass licked one time before but this was the first time I’d had a tongue in my ass. I groaned again as she probed deeper and deeper. When she started to fuck me with her tongue, I whispered, “That feels great.”
She continued with her tongue in my ass but now she was running her hand up and down on my shaft. I groaned softly and pushed my ass back slightly against her face. She whimpered, moaned, and tongued me faster. A minute or so later, she lifted her head and groaned loudly.
Laying her head against my ass, she whispered, “I know exactly what that feels like so doing it makes me know what you are feeling. If I was horny before, I’m fucking horny now and your dick feels harder than I’ve ever felt it.” She gave me a hard squeeze and I had to agree with her.
She shivered and sat back on her heels. I heard the cap on the lube snap open. A minute or so later, her oily hands gripped my shaft and she twisted them back and forth as she ran them up and down my shaft tightly. I groaned and moved my hips up and down.
“That feels good, I take it,” Grace whispered softly.
“Oh yeah. I’d be careful or you’re going to make a big mess on the bed.”
She giggled. “I hadn’t thought of that. Maybe I need to get a towel.”
“That’s probably a good idea,” I told her and groaned again.
She let go of my dick and got off the bed. I looked around to see her going into the bathroom. She came out a few seconds later carrying a big beach towel. I watched the double-ended dildo sway back and forth, as she walked toward the bed. It was shiny with oil.
I came up on my knees and she spread the towel under me. She made a whimpering sound as she crawled up on the bed behind me. I grinned at her as I went to my hands and knees. “So, you’re enjoying your new dick?” I asked as I lowered my chest to the bed.
With a shuddery breath she whispered, “It moves inside without anyone touching it. That alone is good but seeing it move and sway in front of me works on my mind.” She paused a moment and ran her hands over my ass. “With you like this…. It makes me shiver just to think about it.”
I chuckled. “Yeah, shiver, that’s a good word. More like chills running up and down my spine in my case.”
“I well understand that feeling,” she whispered as she leaned over and tickled my asshole with her tongue again. I relaxed and enjoyed the feelings.
She moved away and I heard the cap on the lube bottle snap again. Then there was a cool drizzle of oil on my asshole followed by a fingertip rubbing it in. The fingertip probed my ass and I groaned as it sank in an inch or so.
“I know that feeling also,” she whispered and then whimpered as she slowly fucked my ass with her finger. I groaned softly as she did. Her other hand moved to my dick and gripped it lightly. When her hand moved up and down, I groaned even louder.
A moment later, her hand on dick was gone and so was the finger in my ass. A few seconds after that, I felt the head of the dildo touch my ass. It was cool to the touch and then it was pressing gently as she pushed with her hips. She groaned at the same instance that I did as it popped through the ring of muscles at the entrance of my anus.
She held still for a second and then pressed on the dildo again. It slid into my asshole easily until her hips touched my ass. She groaned and whispered, “The toy moves inside me and those knots rub my clit.”
When she moved her hips back, we both groaned softly. She stopped with the head still inside me and whispered, “I’m going to come hard in a very short time.”
I chuckled and nodded. “Me too.”
She pushed forward and started to fuck my ass with full slow strokes. She was whimpering as she pulled the dildo outward and moaning as she pushed it in. Her hands went to my hips and she pushed in harder and faster but pulled out slowly. I groaned as the soft shaft rubbed my prostrate, my dick twitching, an itchy feeling coming from it.
Grace continued to fuck my ass for several minutes. Her moaning and my groaning were both getting louder and sharper. Suddenly she stopped moving her hips back and forth. They were against my ass and I could feel them jerking both inside and out as she came.
The dildo was moving in quick short movements that rubbed me in just the right way. I could feel my orgasm rising quickly and I tried to clamp down and hold it off. That was probably the wrong thing to do. As my ass tightened, the dildo rubbed my prostate even more firmly. That was all she wrote and I came with three long hard spurts.
We ended up on our sides with the dildo still in my ass. Grace was whimpering softly, her hips giving a little twitch ever so often. My dick was still as hard as a rock and the head was sensitive as hell as she moved her hand slowly up and down along its length.
After a while, her hand stopped moving, as did her hips. Shortly after that we were both asleep.
I woke up from a weird dream about fucking someone and being fucked at the same time. Only it wasn’t a dream. Grace was straddling my hips, my dick buried in her sopping wet pussy. The double ended dildo was still in my ass but I had a feeling the other end was in her ass. She had one hand on my chest and the other was out of sight behind her hip. I grinned up at her but her eyes were closed as she slowly rocked back and forth.
“Ride em cowgirl,” I said softly and groaned as her hips moved a little faster. The dildo in my ass moved faster also.
Her eyes opened and she grinned down at me. Then her eyes closed again. I reached up and caressed her breasts for a moment before I got a grip on them and massaged them firmly. Her back arched, thrusting her breasts out and she moaned deep. Her hips rocked faster and I started to lift my hips as she came forward.
Grace’s mouth opened but no sound came out for several seconds. Then a wail started deep in her chest and steadily grew in volume until it was a yell. Then her hips went wild as they jerked and bucked on my hips. I could feel a hot flood around the head of my dick and down my shaft as she came harder than ever before.
Then I was coming right along with her, a deep groan coming from my lips.
Needless to say, she didn’t make it in to work that day or the day after that. Most of the time was spent sleeping butt…