How do you like to be pegged?
07.06.2025 04:23
She then gets off me, grabs a pillow and tells me to lift my hips up which I do and she slides the pillow under. She hits the plunger a couple of more times and strokes her cock getting it lubed up nicely. She lifts my legs up and has me rest them on her shoulders, I’m still fairly relaxed from the night before, but it takes her a little work to get inside me. Once she does she gives a few squirts again with her first few strokes…then asks me if I am ready and I moan a oh yeah. She starts slow as I relax a bit more and stretch out to take her. She then pushes my legs up a bit and out with both hands, I kind of laugh and say that’s my favorite position with you. She giggles and says ya, but now it’s my turn to pound you. I laugh but she’s not as she quickly picks up tempo and starts making that clapping sound with her hips slamming into my ass. She pushes my legs further up and is going to town. I’m moaning and she is watching as her cock slams in and out of me, saying how hot it is…then starts shaking as she orgasms. I have the plunger so I depress it once…twice enjoying that sensation and tell her to keep going. She is shaking and tries to keep the tempo going and I’m close too. She says let me know when you are going to come and I laugh and say I’m there…she pulls out of my ass quickly…and puts my legs to the side. Moving up in the bed straddling me and slides down on my cock hard saying I want you to cum in me now. It only takes four pounding strokes up and down and I start exploding inside her, and she cums again too. I shudder as I have a second orgasm from all of the prostate stimulation and she then collapses on me. We cuddle for a bit, she’s sweaty and shaking still and so am I. The alarm finally goes off, so she slides off my semi hard cock, dripping a bit on me and the bed and said she has to get ready. I get up, and since she’s in the shower I clean up a bit with a washcloth, slide on a fresh pair of panties, and my skirt and top from the night before and go to the office to start working. My ass is a little bit sore from all of our fun, but it’s a good kind of sore. 45 minutes later she comes in to give me a kiss goodbye. She asks if we can have another pegging session tonight when she gets home. I laugh and say hell yes…she gives me another kiss and says good, lifting her skirt and I can see she has her Lovesense lush inserted and is wearing a pair of her lacey VS panties over it to help hold it in a bit. I laugh and say work is going to be much more enjoyable today! She gives me another kiss, slides her hand up my skirt grabbing my cock and says don’t cum today without me. I left your toy (Lovesense Edge) on the bed so I can play with you too. As she’s walking out she says, oh and I picked out an outfit for you to wear once you get cleaned up too and leaves for work.
She then got up and pulled her skirt off and put on the harness with the new ejaculating dildo on. At this point I was rock hard and I was still enjoying the sensations of the thrusting dildo and was still riding it watching her. She giggled as she depressed the plunger a bit and saw a little “cum” squirt out…wiping it off with her finger and licking it off. She said it doesn’t have any flavor, but it looked a lot like my cum. She held her finger out and I tasted it and said ya, it doesn’t have any taste. She then grabbed my head and said here go down on this and lube it up a bit with another giggle. We’ve never done that before, but I obliged as best as I could. I stopped riding on the dildo resting all the way down on it as it continued to thrust again, as I tried to take as much of the new toy in my mouth. She was enjoying it, saying how watching me was making her turned on…all I could do was mutter a little Mgrrh, as I had half of the dildo in my mouth, trying to take more and ended up choking a bit. She giggled at that and said now you know how I feel deep throating you. I didn’t get a chance to respond as she pushed me back on it so I again went down on it sliding my mouth up and down, and reaching between her legs to finger her a bit. I love it when she gives me lots of eye contact during blowjobs, so I did the same for her. As I increased the tempo of my “blowjob” for her, I increased the tempo of my fingering. I kept looking up at her and she still had her left hand on my head lightly pulling be a bit back and forth. She moaned and said I understand why you love it when I make eye contact. I could tell by her breathing she was getting close to cumming again, so I just started sucking on the tip and licking around it. She breathed a deep moan as she was looking down at me and said I’m cumming and I could feel her tense up on my finger and her legs start to quiver. I was licking the tip as she hit the plunger, cumming on my tongue, in my mouth and a bit on my face…I was surprisingly turned on by this. She is great at blowjobs and so I mimiced her, licking around the head and cleaning it off and she pushed me back down a bit on it and depressed the plunger again…I moaned and swallowed it all as she was still orgasming. She pulled out of my mouth, leaned over and licked the cum off my face saying how that was so hot.
I kept riding it, just enjoying the thrusting and getting myself a bit more relaxed and stretched out, but not to the point of cumming. I take a break for a second and slide all the way down and sit on it with it still thrusting and am taking a drink of wine and I am about to text her again when the garage door opens. It’s directly off the kitchen so it has a direct view of the stools where I’m sitting, and it’s my wife. She said I couldn’t wait any longer so left a bit early and wanted to walk in on you as she giggled. She walked over, gave me a kiss and said I’m glad you are home early…she took a drink of wine, slid the glasses out of the way and hiked up her skirt, pulled off her panties and climbed on the counter in front of me spreading her legs. She grabbed my head and pulled me between her legs, saying finish what you started…and keep riding the cock at the same time but don’t cum yet. No problem for me, she was super wet and it was so hot riding the dildo as I went down on her, it only took a few minutes to make her cum…she rested for a second as I continued to lick her pussy.
Next thing I know I wake up to giggles and my wife laying next to me on her back, it’s 6:30 and our alarm won’t go off for another 30 minutes. She fell asleep with the strap on and nighty tented up. I’m still wearing my stockings, garter, bra and breast forms. She is lightly stroking my cock and it feels good, definitely a great way to wake up. We both have morning wood she said giggling, which even half awake made me laugh. She sits up and starts going down on me, so I reach up her nightie and start fingering her, then pull her over so we can 69. She tells me not to cum yet, but it’s hard not too with her taking me all the way in her mouth and sucking on my balls. It’s a little awkward on my end since her dildo keeps poking into my chest, but I eagerly start licking and fingering her pussy again, which gets wet. I tell her to sit up so she does, and I can get at her a bit easier…I slip a finger in her ass too which elicits a moan. She is into it and starts riding my face until she cums and I have her juices all over my face…and she hits the plunger on the dildo, which shoots a load all over my bra and tummy and we both laugh about the role reversal.
I then hiked up my skirt, climbed on the barstool and placed the head of the dildo between my cheeks and taking a pic and sending to my wife. Again I get an almost immediate response saying how she likes my outfit choice…and my ass. I get a pic back of her fingering herself at her desk…it’s a good thing she has her own office lol. Seeing how turned on she was, now I was super turned on too. I went and grabbed some lube, and a new squirting dildo she had purchased that we haven’t had time to try. It’s a bit longer at 10″ and a bit girthier too. She has a cum fetish so it’s definitely something we want to try. She also has a size fetish as well saying how she likes larger ones so she can watch my ass stretch around them in reverse cowgirl. She spend a lot of time looking for a larger squirting dildo since we also have a 12″ and a 16″ she enjoys pegging me with too.
I lubed up the suction cup dildo and my ass slowly sliding it in and all the way down resting with it balls deep in me. Then I loaded up the squirting dildo, placing it on the barstool next to me. I took a picture of the suction cup dildo balls deep in me and sent that to my wife, and another with her new toy in the foreground and me in the background with the dildo halfway out. Again she responded immediately and said, don’t cum yet…I want to make you do that. It was about 4:40, so I climbed off the dildo for a second…opened a bottle of wine and poured two glasses. I then turned on the dildo, just putting in the tip at first as it was thrusting, and started a video…then slid myself all the way down, wiggling my ass and then all the way up and down clapping my ass cheeks into the barstool a few times. I sent this to my wife and told her “I think I’m ready for you”. All I got was a response of you are going to get me fired lol.
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I’d say on average she pegs me a couple of times a week, however we’ve had a bit of a dry spell the past 2 weeks because work has been so crazy for both of us. We’ve only had time for some quickie sex lately, which is always good too. Yesterday, I was really craving a good pegging from her and texted her telling her that, and she said she was too since it had been too long. Fortunately for me I work from home so I have quite a bit of flexibility with my schedule. My wife usually gets home from work about 5:15 so I planned to be ready to go when she got home. I took a later lunch at around 2:30, giving myself a good enema and a good shaving touch up…I guess I kind of enjoy the prep knowing what’s going to happen later with my wife. I sent her a quick little sext message, with a picture of my junk…she responded immediately and said I was such a tease…but to send more. We also enjoy incorporating cross dressing frequently, and especially with our pegging sessions. After I got cleaned up and ready, I picked out a nice outfit. First picking out my favorite red crotchless teddy with garters and putting it on, along with my breast forms, taking another picture and sending it to her. She responded immediately again…saying how she can’t concentrate on work now. I then picked out a black silk sleeveless blouse, black thigh high stockings and connecting them to the garters. Taking yet another picture asking if this outfit looked ok. I received a response back quickly again, with a picture of her up her skirt, pulling her panties aside of her pussy and saying how she was getting wet. I could tell she was from the picture and now I was turned on even more.
She stood up saying now it’s your turn to cum…stand up and bend over the counter. I didn’t hesitate, sliding off the suction cup dildo with a slight pop, stood up and assumed the position with my elbows on the counter. She spread my legs out a bit wider so I was a bit more level with her and placed the head right at my butthole and depressed the plunger again as she slowly pressed against me. The extra bit of fresh lube helped and the head eased in…making me gasp a bit and her giggle. She said how she loves when she first enters me and seeing my reaction…she slide it a little further in, depressing the plunger again. It was kind of a weird sensation as I could feel it squirting inside me, but I liked it. She slowly slid in all the way, giving me two more squirts until she was balls deep in me. It felt good and she said how she liked how this dildo stretched me out too, taking a picture with her phone. I put right hand between my legs to start fingering her, and she pulled it away and said no…it’s your turn. She slowly started stroking the full length in me, giving it time to stretch me out more. Moaning a bit as she did it, she started increasing the tempo, leaning over me a bit and putting her left hand on my ass to brace herself and reaching around and grabbing my throbbing cock with the other. She hit her rhythm quickly, stroking the entire length in and out as she matched the temp with her right hand. She was really getting into it slamming her hips into my ass cheeks and making that lovely clapping sound…as I braced myself and started pushing back into her with each stroke. She only stopped stroking my cock once, reaching back just to slap my ass, tickle my balls and say cum for me baby. As she reached back and started stroking my cock, I exploded all over. She kept going and started to slow down, but I reached back and grabbed her ass and said keep going. She giggled and said ok and kept pounding into me as I pushed back into her. She leaned back and was grabbing me by both ass cheeks…slapping my ass on both sides too. I could feel the tingle as a prostate orgasm was coming…she could to and said I’m going to come too. I reached between my legs to finger her and I started shaking as I had a prostate orgasm…then another and she kept going until she came again…she had hit the plunger again as I could feel it spurting inside me. She stopped and layed on my back to rest a bit. I said lets go outside and enjoy some wine, so she slowly pulled out of me…giving me a good hard spank on the ass saying that was long overdue.
Yes, very much so and I feel fortunate that my wife enjoys it too as well as quite a few women that I dated before her.
We enjoyed our wine out on the patio for a bit, she had only slid her panties back on with the cock sticking out the top and still had her stockings and work blouse on. I was still wanting more, so I had slid the thrusting dildo which was still going inside me, and my thong panties back on to hold it in. We sat outside for about 10 minutes talking and she started to go down on me, which felt good but I was still in recovery so she stopped and just made out with me for a bit. About 20 minutes later I was ready to go as soon as she went down on me again. She sat down in her chair again and said, your turn to ride, stroking her “cock” and said she needed to rest a bit still. I laughed and said yes man, pulled my skirt back up, panties off and thrusting dildo out and straddled her. Sliding myself slowly down on her. I was still pretty well lubed up, but she gave another squirt inside me and another as I pulled all the way up with just the head in my ass. Game on, I slide all the way down on her and we started kissing as she stroked my cock. I sat up a bit more and started pounding myself down into her…it only took a few minutes and when she said she wants to swallow me, as soon as I could feel it coming I stood up and she took me in her mouth all the way, spreading my cheeks and sticking two fingers in my ass to push on my prostate I came hard again, down her throat and on her face a bit too. I laughed and she said that’s payback giggling. She cleaned it off her face and we sat outside finishing our wine. Finally going to bed, I was still wanting more but pulled my skirt and blouse off and she changed into a nightgown and still had the harness and cock on. She was giggling about it tenting her nightie and how much she liked the new toy…me too I said. It’s nice to not have to stop and lube up and it feels good when you cum inside me. This made her laugh and we kind of snuggled and watched tv, I dozed off at some point.
So next I got out one of our suction cup dildos which is my new current favorite. It’s an 8″ thrusting and vibrating one from Lovehoney, sticking it to a barstool at our snack bar in the kitchen.
Tonight should be a fun night again catching up on our lost pegging sessions!
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