Sunday, January 24

Sensual Spanking in Front of Trainer

I've been meaning to demonstrate to david's fitness trainer, Mags, that spankings can have a lighter, more sensual side as well, as she seems to have just "one speed" as one of my commenters mentioned. To this end, I wanted to setup a situation where I could give david a more sensuous spanking, allowing Mags to be a voyeur. david's spanking would include a red bum for sure, but also a lot of caressing and fondling, lots of massage oil, a little bumhole play, and an ejaculation while across my lap. I also thought it would be nice, after her having explored the anatomy of it last week (see Sexy Trainer Explores Husband's Bumhole), to have Mags see a practical application of prostate stimulation in an erotic/ejaculatory setting between wife and husband.

I am very keen to involve Mags as much as I can, as it's rare to have such a situation "on tap" and both david and I really enjoy the added excitement of having a second woman involved, even voyeuristically.

It so happened that I was home during david's training session, so I decided to get in some cardio while I watched Mags train him. I've been hitting my own cardio pretty hard lately, doing a half hour of heart rate interval sprints (to 80's disco music on Spotify!) every day I'm not otherwise in the gym.

We all arrived in the home gym at pretty much the same time. I was a bit ahead so I got the tunes going. As I was there, which was unusual, Mags asked if she should spank him that day? When you think of it, it's an odd question. I was the one who setup this arrangement, and she knows I approve. But I guess she is nonetheless bashful to spank my husband when I am there. As I wanted to show her the lighter side, in fact I didn't want him spanked by her today.

"Not today," I said, "I'm going to give him a more sensual little spanking right afterwards myself. A 'good boy' spanking. Would you like to watch that?"

"Sure!" (She's always game!) "What's a 'good boy' spanking? Has he been a good boy?" she asked

"Yes, he has been a good boy," I answered. "It's a spanking, but a little more sensuous, less of a punishment, more of a reward, a lot of fondling, some prostate play, an ejaculation from him, that sort of thing."

"Hmmm. That sounds like fun to watch. Are you sure you want me there for that?" She asked.

"Oh sure. He has nothing to hide from you, especially after last time," I answered. "and I thought it would be nice for you to see the lighter, more sensual side of spanking."

"Well I'm always interested," she answered enthusiastically.

I always enjoy demonstrating my sexual control over my mate to other women. It's my little fetish. The thought of making david squirm across my lap and force a cum from him (he has no control) in front of pretty young Mags turned me on. She might have the youth, the tight hard little body, the looks, but I have my very own man to do with as I pleased!

That having been settled, I started in on my cardio and Mags started in on david's training. While we were exercising, I asked her about last week's bum play. I said that david had told me all about it and it sounded fun and educational.

She answered that it had been very interesting, and a real learning experience for her. She said that david had mentioned that some women use strap-on dildos to fuck a man up the bum. She was intrigued and did some "Internet Research" (her air quotes) on the subject. She seemed genuinely surprised (and if I read it correctly, a little delighted) that women use strap-on dildos with other women. That comment excited me a little, as I had never done that with another woman, but might like to, you know, fuck a pussy... I don't know if Mags is into girls at all. I put that thought on the back burner to explore later. I had really enjoyed my recent hotel experience with a girl, "cuckolding" my husband, which he seemed to enjoy as well (see Girl Sex with the Escort!!!!). Maybe it would be fun to fuck a girl. Or maybe fun to get fucked?

"I was hoping he'd have a strap-on here for me to use on him," she continued, a bit saucily I thought. Maybe jokingly? It was tempting to change my plans to a butt fucking for my husband, but I thought I might want to think about that one a bit more first. But I didn't want to discourage it. It would be fun to include "butt fucking" as an additional tool in Mags' motivational training arsenal for david, as only the overly fierce butt whippings were maybe getting a bit old for him. I guess I'm really not the jealous type, as the thought of the attractive twenty-something Mags butt fucking my husband was just fine with me. Not sure if I necessarily wanted to be there. Quite sure she needed to keep her clothes on during. But other than that? Sure. Why not? Go for it.

"Let's ask david what he thinks," I suggested. david was on a bit of a between set break. "david, what do you think of me allowing Mags to include more anal training, with the strap-on, into your sessions?"

Ha Ha! david blushed and stammered as he signaled he could support that. So sweet!

"Let's see what you really think. Take your pants and panties down to your knees and put your hands on your head," I commanded. david instantly did so, revealing the start of an erection. His penis had thickened and lengthened, but was still pointing down at a forty-five degree angle.

"What do you think..." I repeated more slowly, "of me allowing Mags to fuck your ass... with a strap-on dildo... as part of your training? Flip you over. Fuck you like a woman? Maybe use the big dildo if you've been slacking? She's in great shape. She can fuck you long time."

Mags was smirking at him the whole time I was doing this.

It's fun to watch the male erection develop, especially in a situation such as this, with two clothed women questioning him, his hands on his head with his pants pulled down, and under the very bright lights of the gym situation.

david's penis sort of grows in spurts. It jerks upwards in a spurt, and then settles down, but higher than it was, and then again and again and again. It did not take very long at all, less than a quarter of a minute for sure, until it was fully erect, pointing upwards, tip engorged and purpled/reddened with the blood.

"What do you think, Mags," I asked her, "do you think david would enjoy adding some butt fucking from you into his training routine?"

"Oh I think so..." she said, continuing to smirk at his by now fully erect and still twitching penis.

"And how about you, david?  What do you think about me allowing you to be bent over that exercise ball for some anal intercourse from your trainer? Would that help keep you motivated?"

"yes ma'am..." he answered sheepishly! Ha Ha!

"Ok then. Next time I'll leave out the strap-on harness and the medium sized purple dildo and Mags can choose if she wants to use that on you. What do you think, Mags?"

"Sure. Put it out. I might use it..." she said noncommittally.

"Here that, david? Mags might use it on you or she might not. Entirely her choice. But if she does use it, then if the way she whips you is anything to go by, you'll be in for quite a fucking! You be sure to keep yourself clean down there, inside and out, before your sessions from now on."

There. That was all set-up. We'll see where that goes. I had david pull his pants back up again and get back to work, albeit by now uncomfortable in his stretched panties!

It was fun watching Mags work him out. Even without the spanking, she was really strict with him! For example, if a squat was not to her complete satisfaction, he had to redo it. Or at one point she asked for 10 pushups, slow and low, nose to carpet each time. If he didn't touch the carpet with his nose (and she crouched down to make sure), he would have to repeat the pushup. david only got halfway through the count, having done so many extras, when he collapsed. But Mags would not let him off the full count. He was allowed to rest for a bit, but then he had to finish the full count of 10. He collapsed twice more before he finally finished the count and was allowed to move on. Apparently, according to david, normally when he wimps out like that his pants would come down for the remaining pushups and he'd be "encouraged" with stripes from the riding crop across the seat of his panties first, and if that did not work then he would have to hold plank as she lowered his panties and continued his motivation, but even more strictly, across his bared ass and flanks next. But hey, I'm not complaining, his chest and arms are filling out nicely!

I extended my cool down to coincide with the end of david's session. Once we were done I told him to run upstairs, have a very quick shower, soap and water, put on his pajamas, sit on the side of our bed, and wait for us to come up so that I could give him his good boy spanking and Mags could watch.

"Yes Ma'am," he said, blushing a bit, and sheepishly ran up to do as he was told. david had never been made to spurt in front of Mags, or any woman with such an age difference for that matter, and I'm sure he was feeling bashful, though still very much desiring it.

I checked in with Mags, making sure she was comfortable with the whole arrangement and everything. She assured me she was having a lot of fun with it, and learning a lot. She conveyed that she did not feel at all threatened by any of it, or concerned about any unwanted 'relationship', and as long as it was all ok with me, she was totally into it. Just a bit of naughty fun and helpful for keeping david "at it" on the exercise front. That was a relief to me. I suspected all that, but it's good to check in every now and then.

I was a bit sweaty from my workout, but not nearly as much as david, so I didn't bother to shower or change. I walked upstairs with Mags and into the kitchen. I opened the drawers and said, "let's see now, what shall we use..." I selected a red rubber spatula I had not used before.

I can't really make an impression on him with just my hand, and need an implement even for a good boy spanking.

We hung out a bit more in the kitchen, talking about strap-on dildos and butt fucking boys of all things. It came out that Mags was very keen to take a cock of her very own for a spin.

We then headed upstairs, and there was david, all cleaned up and waiting for us on the side of his bed in his red plaid pajama bottoms.

I would be giving him his spanking with me seated on the side of the bed where he was now. He would be getting up and going across my knee and having those pajama pants lowered bit by bit until they were at his knees. Mags settled herself on a swiveling desk chair we have in the bedroom in prime position to watch his spanking.

I opened the bedside drawer and got out the Baby Oil. I put it and the spatula on the pillow. Then I went to get a towel. I told david to stand up, and I took his place. I then put the towel down across my lap and knees. We all knew what it was for. My husband would be spunking while across my lap, and this towel was to contain any mess that might escape. He looked nervous and excited to have this done to him in front of Mags.

As usual, and as david well knows, the spunking is not guaranteed. He might be asked to do or say certain things, or make certain promises, or beg to be allowed his ejaculation. If he does not seem genuine, he might not be allowed his release at all (that has happened more than once in similar situations - he knows it does not take much). If that happens, he'll be made to stand up with his wet, dribbly, and throbbing erection on show, apologize to Mags that he wouldn't be allowed to ejaculate in front of her, for her viewing enjoyment, and then stand with his nose in the corner until his excitement abates, whereupon a strict butt-blistering session with my strap is more than likely for disappointing my plans.

As it was, david came across my lap. So cute in his little PJs! I inched the waistband down to just the very tops of his legs, baring his bottom. I then used my hand and began spanking him lightly all over. I could feel david squirming, and his erection pressing against my thighs even through the PJ's, towel, and my tights. I put my left arm over his waist holding his bare flank into me with my hand. david squirmed and bucked a little, and kicked his legs slightly while moaning with pleasure at the light spanking. I looked at Mags and smiled, and she smiled back and raised her eyebrows at me.

I pulled the waistband of his PJ's down a little further, exposing some of his upper thigh, and included that area in my spanking. With the PJ's still up in front the waistband had the tendency to rise back up over his thighs, but not over the crest of his buttocks. So I had to repeat the pulling down several times to keep his upper thighs bared (I knew what was happening: I didn't mind, I like pulling them down). Each time I pulled them down you could see his balls poking through a bit. Mags was in front of me and to my right, so she could see what I was doing quite clearly. So it was basically me repeatedly pulling his pants down to bare the backs of his balls for Mags to see.

"I think I need a bit more than just my hand to redden those cheeks," I said as I picked up the wooden-handled, rubber-tipped spatula. I started spanking with that, and it was very satisfactory. I started getting some nicer shades of pink towards red. I had to hold the waistband down while I belabored his upper thighs with the spatula. Meanwhile, david started moaning more and shaking his bum and even raising it for the spanks, and kicking his little legs more, like a girl. He reached his left hand around and grabbed me around my butt. It's ok. I encourage this. It's ok for him to touch his wife like this during a sensual spanking.

"I hope you don't grab Mags' butt like that when you're across her knee!" I chided him.

"No Ma'am," he said. "Only you."

"Damned right," added Mags.

"That's a bit redder now," said Mags. I agreed with her.

I put the spatula back down but within reach, and worked his PJs down so that the front waistband was also pulled down. I arranged them to band around his upper thighs. I got the baby oil and dribbled some on his butt cheeks and crack. I massaged it into him, reaching between his legs (which he promptly spread for me) to massage it into his balls and along his cock as well. I pulled his cock out so that it lay to the outside of my right thigh. Sitting where she was, Mags readily saw his hard penis nestled against the side of my leg over the towel. I then continued hand spanking him over his oily bum and thighs, including now his inner thighs as well.

I got the spatula again, and started increasing the intensity of those spanks, all over his ass and thighs, trying my best to cover every inch from waist (lightly lightly up there) to mid-thigh, down his flanks as well, inside his legs, and inside his cleft. By now the spanking was pretty hard. If one starts with a spanking this hard, it would be a punishment. But built up as it was, it was more of a pleasure for him, though a painful pleasure that had him intensifying his bucking and moaning and squirming and kicking. I felt him grab my ass more tightly, which I took as encouragement to spank him harder with the spatula.

Mags meanwhile was enraptured by all this, looking at it all very intently. She had never given a sensual spanking, only a punishment spanking, and I guess it was an eye opener for her. For my part, I absolutely love spanking him in front of another woman, and loved exercising my dominance over him in this way.

I put the spatula back down. I wouldn't be needing it any longer. I lowered his PJs even further, right down to his knees. I reached under and grabbed his cock and balls, and pulled them up between his legs. david knew to close his legs, clamping his ridiculous genitals there for easy access. If you could see his front, it would look like he had a pussy there.

This is literally the view that Mags and I had, with david's hard cock and spanked cheeks on show, ready to be very humiliatingly milked by me in front of his trainer.

I dribbled more oil onto his shaft and balls and ass cleft and started massaging it in again. As I stroked his cock david raised his ass high. The thing with this cock and ball position is that if he is more flat it's painful on his balls, and clamps him preventing an ejaculation. But if he raises his ass higher it takes the pressure off his balls, and allows for an ejaculation to occur. As a result, he jacknifed himself up, raising his ass in the air over my lap. Of course, this required teasing...

"Look at you, you little slut! Waving your ass in the air like that. Shame!" And with that I gave him a few light hand spanks on his cheeks. "You'd almost think he wants my finger up there," I said, referring to the fact that as he raised his ass, he opened up his anus for us both to see.  I looked at Mags, parted his cheeks, and ran my fingers all over his bottom hole.

"I think he does," she said with a smile in her voice as david moaned from the anal massage.

So I slowly inserted my finger into his bumhole.

The oil allowed for an easy passage. I penetrated right to the hilt. david moaned as he was penetrated. I used my left finger for this, leaving my right hand free to spank him all over his cheeks and also fondle his cock and balls. I had to turn my left hand to be vertical and palm facing towards his feet so that I could finger fuck his prostate correctly.

"Are you a bad boy?" I asked him teasingly. "Tell Mommy who's her bad little boy." It turns him on, but he gets embarrassed easily by "Mommy play". I wanted him embarrassed in front of Mags.

"I am..." he said.

"You are what?" I elicited.

"I'm Mommy's bad little boy..." he responded correctly.

"Awwwww. Mommy's boy," teased Mags as if on cue.

david was by now very close to an ejaculation. I could feel the pre-cum. I rubbed his tip and then held up my palm to look at it. I wiped it on his leg, and did it again. He was very frustrated that I didn't continue with the fast rubbing, and waved his ass around ineffectively in the air, begging for it.

"Now, now. Does baby want to cum?" I asked.

"Oh yes, please!"

"Beg Mommy for it." I said.

"Please Mommy! Please! May I please cum???" said david, losing all modesty completely. I love how when grown men are in this state, nearest their orgasm, they'll say or do anything.

"After you cum, you'll have to eat it all up. Swallow it all down. The whole load. Right in front of Mags. Do you promise to do that?" I asked him.

"YES! YES PLEASE!" he practically screamed. He was on the very edge of a very ruined orgasm.

I gave him a few more hard and fast strokes to his shaft and tip with my right hand, while pushing down hard on his prostate with my left. I then pulled my finger out of his bumhole (like for anal beads) and he started cumming. I had to move fast to catch most of his ejaculate in my left palm. There was a lot! It kept coming and coming as I squeezed it out from the tip into my palm. david bucked and moaned as he spent himself. I continued until he had calmed down again.

"What do you think?" I asked Mags, showing her his ejaculate in my hand.

"I think he needed to cum!" She said, referring to the quantity of spunk in my hand.

"On your knees, sweetie. Time to keep your promises." I told my husband.

He slowly moved off my lap and collapsed to the floor. He picked himself up to kneel facing Mags and I. I made him hide his genitals back between his legs, telling him that since he came like that he would have to swallow looking like that. Looking like a girl with a pussy, which was fitting given the task at hand.

"What did you promise to do before you came?" I asked him, showing him my hand with his ejaculate in it.

"Swallow..." he said.

"That's right, like a gi-irl... Every last drop." I said.

"In front of Mags?" He asked pitiously.

"Yup," I answered succinctly. "Come on you little cum bucket, down the hatch." As I said that I held the back of his head with my one hand and presented my palm to him right in front of his mouth. He bent down a little and licked it up off my palm.

Mags had a little "Ewwwww!" expression on her face as he lapped up the cum like a good little doggie. I was thinking of asking Mags if she does this at all, but decided it may not be appropriate right then, depending upon the answer.

"Hold it in your mouth before you swallow." I told him.

david cleaned my palm and sat there on his knees with his mouth tightly closed breathing heavily through his nose.

"Now open up. Show Mags the cum in your mouth."

david opened his mouth and Mags got up off her chair to come over and peer into it. Some of the cum was on his lips as well, like in the photo below. She also looked down at his absent genitalia and giggled at that.

"Now swallow it all down, sweetie, like you promised," I told him. He closed his mouth. I grabbed his nostrils shut, and tilted his head back by his hair as he gulped down the semen in his mouth. You could see his throat move as he swallowed his load.

How humiliating is that? That he has to first show her the load in his mouth, and then actually has to swallow in front of a young lady like that. It's not the sort of thing he is ever likely to live down with her. Given that Mags likes her sexual partners to be manly, it certainly does no harm for her to see him reduced in status like this by way of this most submissive womanly activity!

When I was sure it was all down I told him to say thank you to Mags for watching his spanking and adding to his excitement. He did so nicely. I then told him he could run off to the bathroom and rinse his mouth and shower again to get all the goo off him. david hurried to the ensuite bathroom, and we heard the water going and the spitting sounds. Mags and I smiled at each other. There's some payback. Ha Ha!

We left david behind and Mags and I went downstairs.

"Well what did you think?" I asked her.

"Very cool. But my boyfriend would NEVER let me do that to him," said Mags.

She got her coat and boots on and I paid her and we said our goodbyes. Boyfriend notwithstanding, I wonder if I can get her into bed with me?

Tuesday, January 19

Sexy Trainer Explores Husband's Bumhole

david got his bumhole thoroughly explored by his pretty young trainer the other day.

Let me tell you, to the extent I know it, how it went down.

As you know, david has an at-home personal trainer, Mags, who both works him out and also gives him spankings. I recruited her via email. You can go back and read all about it in New Trainer! and follow-up posts. She is young and keen and very game. In fact, she is in her early twenties and david is pushing forty, so she is "half his age" and "young enough to be his daughter", all of which adds to the fun!

The other day the two of them got to talking during training and the subject of bum fucking came up. Don't ask me how. I was not there. Mags, who is very naive in certain ways, asked my husband "someone once told me that guys have, like, a G-spot up their bum..." According to david, she said it in such a way that if it turned out to be totally false she could laugh it all off and say she never believed it anyways.  david earnestly told her that, yes, in fact, there is such a spot and it's called the prostate. Mags then confirmed that her boyfriend would never let her get anywhere near that part of him anyways, and they went on training.

When david related this to me I decided I just had to donate david's bumhole to the cause of this young woman's education. I texted her telling her that next time she came I would have david lay out gloves and lube and she should feel free... She txt'd back "sure!" What did I tell you? Game! (She also knows she is likely to collect a little bonus from me also - fun and profit.)

I wasn't there for it, but the following is how david told it to me.

Before she arrived, david had laid out a pair of latex gloves, a tube of lube, some paper towels, a plastic bag, a Lux vibrating prostate massager, and a diagram of a finger touching a prostate.

He had also cleaned himself very thoroughly, inside and out.

david showed her the stuff and she giggled. He told her about how she's very welcome to explore back there. To make her comfortable, he told her the story of going to visit his (female) doctor and of having his prostate examined and developing an erection. She enjoyed that story and questioned him about some of the details. She thought it was very funny that his penis was bare and he was erect and a bit dribbly in front of his doctor when she had a finger up his ass.

To david's surprise, despite the warm start, she ignored the stuff and told him to start his exercising with some in-place running. After he was warm she picked up the leather belt and told david to bend over the exercise ball. He lowered his gym shorts and panties, hoping for a bum exam. She wrapped the buckle end of the belt around her hand several times and used it single-tail to whip his bare behind.

Her whipping of him had its usual ridiculous severity, and he was soon howling under her strictly applied lash.

When his bum was adequately sore and marked, then she had him start in on an exercise set. Between exercises she whipped him some more. When they were through the first set she said, "ok, let's try this out. Bend over the ball".

david, heart beating, took his gym shorts and panties right off, and bent over the large exercise ball bare from the waist down, legs spread, and penis and balls hanging down between his legs. He was very much hoping it would be a probing and not another whipping as he lay so very exposed to her.

Mags put on the latex gloves. david then felt her dribbling lube on his bottom hole. The diagram of the prostate was arranged right in front of her, at david's head where she could see it. She penetrated him with her finger. david felt she did not have enough lube, but did not say anything. She was reaching for the prostate, but despite the map was reaching her finger in the wrong direction. david had to tell her to turn her finger around and press downwards towards his front. She rooted in there for a while, and then david said "that's it!"

"Oh yeah, I feel it!" she squealed in delight. "That's it? Does that feel nice?" She asked. "It's smooth." She commented.

"yes... that's... nice..." said david. (Ha Ha!)

She fucked him a bit with her finger, in and out, and in and out. david figures she spent a good couple of minutes in there. His penis visibly stiffened as she did this, but she did not comment on that.

"Ok, back to work!" She said. She pulled her finger out, and took the gloves off.

As david pulled his panties and gym shorts back on, he also showed her the prostate massager and explained what it was for.

She asked a few questions, such as how does it go in, and david also showed her how the vibrating feature worked. She seemed interested in an abstract sense, but didn't say she would use it on him at all. She made david go back to exercising, and alternated with the spankings as usual.

When david was finished all his exercising, and there was only stretching left, she said "Get back over the ball, let's try this out," picking up the prostate massager.

My husband again stripped himself below the waist, and again bent over the big exercise ball. She put the gloves back on and lubed the massager, and started inserting it. At first it would not go, but she bumped, bumped, bumped it against his anal opening, and eventually it went in, which apparently delighted Mags. She turned on the vibrating action and david moaned like a slut.

She asked if it was on the spot? david said it was. Then she grabbed it in her hand and started fucking him with it. In and out and in and out. david moaned each time it went in and she shushed him with a "Shhhh!", but he kept moaning regardless, and she kept fucking regardless. She put one gloved hand on his ass while she fucked him with the other. The she moved the hand on his ass to between his legs, and pushed down on his penis and balls, pushing them into the exercise ball between his legs as she continued the fucking. david moaned and bucked and squirmed during this treatment, and she continued fucking him and shushing him, seemingly a bit embarrassed by his carrying on, perhaps afraid I might come home and hear him, or maybe she just objected to a grown man, old enough to be her father, moaning like a slut under her hand.

david swears he was moments away from spurting when she stopped, pulled the vibrator out, and put it down on the top of the elliptical machine on the towels. david stayed bent over and moaning for a bit as she laughed at him. I'm sure she got an eyefull of his asshole lubed and gaping open, and his cock hard and wet with pre-cum. But that's all he got.

Her view of my ridiculous husband.
Yes, a hard little bum-fucked bitch.
He only wishes he got to touch himself and dribble that much!

As david calmed down, he stood and pulled his panties and shorts back up over a huge erection which she pretended not to notice at all. david was relieved and pleased that there was no visible mess at all to clean up. He had done a good job preparing for her.

She said "Time to stretch."

david got a gleam in his eye and asked, "may I stretch with the plug in me?"

"Sure!" she answered.

david pulled his pants down again, and right in front of her, as she watched with a little smile on her lips, stuck the massager back into his own bum, erection bobbing in front of her, turned it on, and restored his panties and shorts for his stretches. He was being stretched in more ways than one!

It was still in there, humming away, as david saw Mags to the door, paid her usual fee, and then added the same on again as my bonus to her.

I do believe a good session from Mags with the strap-on dildo is not far behind!

Tuesday, January 12

Saturday, January 9

Update on Baby jessica's Halloween

One of my pen pals is a youngling named jessie. You can read about jessie in some earlier blog posts, the last one being this one where I sent "her" to buy and use some feminine hygiene products.

After a time, jessie wrote me back...
Anything else I can do Ms. Julie?
I think it's time for a bra, sweetie. Off you go to a lingerie store to get fitted. Ask for breast forms and a bra. They are to wear in private, not out in public at all, but I do want you wearing it in private to get that "real girl" feeling you can carry around with you all day.
You're.. you're probably right I guess Do I have to get fitted? They'll know it's for me! And no breast forms or bra in public right?
Of course you'll be fitted and of course they'll know it's for you. You will have to try it on, especially the breast forms. I can assure you the salesladies are quite used to cross-dressing males and even seem to enjoy the interaction. They even have a policy at Victoria's Secret and at Nordstrom's of being tolerant. So they have fun with it as a result. And no, not in public (except I will want a photo, of course, for my private enjoyment!)
I'll get right on that bra shopping. I'm actually getting excited since I've had to wait. And I was even considering asking my girlfriend to come with. Is that a bad idea?
No, that's a great idea! I think it eases things if you have a woman helping you shop.
After a bit of a delay, jessica finally got back to me.
Sorry it's taken me so long. I did go though with it, Ms. Julie. And actually I told my friend I wanted to get a bra. And we talked about it a bit, and then she came with me. And... then... I lost my nerve. We walked right by Victoria's Secret. Didn't go in at all. She was a bit annoyed, and I felt bad. I made her waste her time with me and we didn't even go in. That was a few weeks ago. Since then I went by myself. Not to VS. I'm just too afraid. My friend told me I have to get measured but I'm scared of that too. So I just went to Target and bought what I assumed would fit me. It does fit I think. This story doesn't have the same drama as my other shopping trips, though. The check-out woman didn't comment on my selection. I just bought one set.
Bad boy! you apologize to your friend, tell her you deserve a spanking from her, and then SWEAR to do it next time if she will only take you. I assure you they are very welcoming at VS. It is a store policy to be sensitive on matters such as these.
We had some more back and forths that I don't want to bore you guys with. jessica was worried she had alienated her friend for good. For some reason, jessica never asked her friend for that spanking. I think she's terrified of the very well deserved fanny pain she would be forced to endure, bare bum across her friend's knee. I understand the friend is quite strong and fit. Some type of athlete. I might have to make her do that.

At a certain point jessie requested another assignment from me. I told her to insert something into her bumhole as she had never done that before, and send me a photo. She sent me a photo of her in panties (!) with something sticking a little out... maybe a pencil? You be the judge.

My response...
You need to buy a suitable ass toy, jessica. Who don't you get yourself over to a sex shop. Have a conversation with the lady there over something suitable to go into your bum. Tell her you want the experience of being fucked like a woman, but you are very tight back there. She'll find something suitable for you (maybe even test it for fit ;-)
And then jessie came up with an unexpected twist
So my girlfriend...the one I said I thought I lost... well I decided to text her because I remember she said she liked plugs. And I thought I could be in for a legit femdom experience. Like your scenes with david except not a scene. I mean she was mad at me at first and didn't want to text. But when I said I just wanted advice on ass toys... well she opened up. She told me she could, quote, "show me some of hers." We've set up a time to meet, so it's happening. Am I reading too much into this? It seems like this might be my first (pretty much ever) sexual experience with someone else. I'm excited and terrified.
Well that's an exciting development! I emailed jessie a week later asking if there were any further developments. I'll let jessica bring it home...

Oh yes Ms. Julie! A lot of developments! I'll embellish a tad little bit with a quote or two but hardly at all. This REALLY HAPPENED and I CANT EVEN I just CANT EVEN BELIEVE IT. I didn't think something like this would ever happen to me.

I went over to her house wearing my leggings and a T-shirt. (I almost exclusively wear leggings now...all the college girls around me do so I wanted to too).

We went into her room, had a little bit of small talk, or girl talk. We talked about boys... she seems to always have a new boyfriend every time I talk to her. She never keeps them very long. Then she brought up why I was there: ass toys.

She said "these always come in handy when I'm between boyfriends. I'm sure they could help you too." she smiled at me.

I looked...wide eyed... at her collection. I've never seen this sort of stuff in real life Ms. Julie. She had a number of butt plugs and a dildo. I told her I had no idea what I was doing.

She smiled again and said "I can help you. Shut the door though. My parents are home."

(oh and I forgot to mention Ms. Julie, she was home for this weekend, which was Halloween weekend, because there was some party she wanted to go to with her high school friends. So she came home instead of having Halloween with her college friends as usual. This was Friday night that I was at her house.)

I went to shut the door. "Damn jessie. Your ass looks alright in those."

jessica sent me a photo after the fact of what she was wearing

I blushed.

"Let's see it a bit better, though. Bend over the bed."

I just looked at her. I don't know why I didn't bend over right away.

"What? Do you want me to show you my toys or not?"

I didn't say anything. but I bent forward on her bed. She put a hand on my ass. All of a sudden she seemed hesitant too.

"Are you sure you want me to do this?"

"Yes," I said.

She put her other hand on my ass and pulled my leggings down, just a little bit to my thighs.

"ahaha" she softly chuckled. "You do look cute in these." She snapped my panties.

ditto for the panties

She hasn't really seen me in them before, but she's seen the tag when she checked and she saw them in my room when she came over before... remember Ms. Julie?

She showed me her dildo. I gulped. I'm not gay.... and... it was so big...

"Anything smaller?" I asked.

"Sure," she grabbed what I think was her smallest pink butt plug. "Let me lube this up. I don't want to touch your ass, but I don't want to hurt you either. It probably will hurt a little, it's your first time."

She lubed up the plug and came behind me.

"Eww! jess!" she cried when she pulled down my panties. "You better shave this little bum of yours! That's the last thing I'd expect to see from a boy like you." The way she said 'boy' made me think she didn't think I was much of a real one...

She started to slide the plug in me. At first... it felt so good... like... oh my I really felt tingly... But then she pushed more. It started to hurt. And like it really hurt. I held quiet. I didn't say a thing. But then I was crying. It hurt so bad. She stopped.

"Jeez jessie. I didn't even get it all the way in yet."

I looked back at her, tears running down my face.

"Okay you've had enough," she started to put the plug away.

"No please!" I begged her to try again.

"Okay. Stop being such a baby then."

I swallowed hard.

She put it in me again. Not far this time. Just poking it slowly in and out. I felt a tingling again. I reached for my penis and flipped it up so I could hump the bed. She laughed and started going harder. It hurt. I kept humping. But soon I was crying again too.

"Will you man up already?" She stopped again.

I whimpered.

"That's probably not the right phrase now that I think about it," she shook her head. "Suck it up maybe."

She handed me a tissue and put the butt plug away.

"It hurts," I said.

"Well if that's the way you want to have sex, then put your big girl panties on and deal with it."

I stood up.

"Oh my God! Don't show me your dick! I don't want to see that!"

I quickly pulled up my panties. Honestly I don't think she saw it much. Not for more than a split second. I pulled my leggings up. I was still sniffling. She sat down on her bed and said I could sit down too.

"It's okay," she said.

Somehow we shared a touching moment then sitting on her bed. Tears in my eyes and her hand on my shoulder. We talked about why she got mad at me before. The biggest thing was when she (really kindly) took me bra shopping when I asked her to and I refused when we finally got there. I apologized. I cried a little more trying to explain how hard it was to buy a bra. Eventually we hugged.

Before I left she started telling me about the Halloween party she was going to (which was tomorrow). She said I should come with her because she had seen the perfect costume for me when she was out buying hers. She wouldn't tell me what it was. She just told me to come back to her house tomorrow morning and we would go out and buy it together.

Well I did just that. We drove to the store. She went and found it and just started cracking up as she held it out to show me. It was a leotard with puffy sleeves and on the chest it read CRY BABY and it came with a head piece and a binky. I got super embarrassed. I tried to say no but she asked me why not? She said isn't this perfectly fitting for you? What could I say? I shrugged. Eventually, I nodded.

We went back to her house. She helped me put it on (it was a little tough to slip in to).

Wow. Not a lot in the "package" is there?

She laughed so hard!

I protested. I mean I was really not happy with this. I would've rather been something else but she just put the little binky in my mouth. I let her and she laughed so so hard. But then she said I did look kind of sexy. And I guess I did. It's a leotard so it's not really babyish, at least not below the chest. That made me happy. But I was absolutely petrified about what would happen at the party. I've never been publicly humiliated before, Ms. Julie. I mean not unless you count my shopping experiences... which arguably do count... but I wasn't dressed in a cry baby suit and that's more embarrassing than just being feminine. You can imagine my inner fear when I went home afterwards to wait for the party later that night.

She came to pick me up. She insisted on driving. We made our way to the party. At least no one here would know me. These were her friends that I didn't really know. Oh and just to say, my friend was dressed as a pirate. A sexy pirate but not slutty in any way. If anything it made her look more powerful, at least to me, compared to me.

We walk in. She hugs one of her girlfriends, and the the girl sees me. She laughs out loud. I blush.

"Who's this?"

"Oh this is my friend, jessie. He wanted to come, I hope that's okay."

"Oh sure! He's cute. This has to be a girl's costume..." she looked at my leotard. Its tightness and my little bulge.

"Yeah I actually picked it out for him. It's very fitting."

"What he's a cry baby or something?"

"Oh yeah." She looks at me and asks, "should I tell her the story?"  I shake my head. "Oh alright, I'll tell you later" she says to her friend.

So we go in. I meet people. It's more of the same. But not always. Some people don't even remark on my costume. I mean it is Halloween after all. People are the most open minded on Halloween it seems. It was a normal party. Eventually I felt comfortable and it was actually really cool because like I said none of the people knew me. I could be the real me. And it didn't even matter that I was wearing a baby costume. Soon I was sitting legs crossed, martini in hand, and laughing with three or four girls.

The first girl I met actually spent the most time with me. She and my pirate friend did humiliate me some. I mean they teased me. My friend said, "Does baby want some yummy appetizer?" I just smiled and shook my head as if to shake her comment off. But she kept going, "Come on. sit on my lap. I'll feed you." I hesitated. The other girl said "yeah come on!" and grabbed me by the arm and pulled me towards my friend. My leotard clad ass plumped right onto her lap. "Here comes the train." teased my friend and shoved a spoonful into my mouth. "I want to feed her," the other girl said, and gave me a bite of her brownie.

All of a sudden I was a 'her'. And all of a sudden we were drawing a crowd. I started to pull against my friend but she held me tight. You know I'm small Ms. Julie. She is stronger than me. One of the onlookers asked if there was any baby food in the house. Thankfully there wasn't. And the feeding stopped. But my friend held me on her lap for the next while. I admit to enjoying it. The humiliation. But I also enjoyed before the humiliation when I felt like a girl.

Afterwards, when my friend drove me home, we talked a little bit.

"You liked that everyone starting calling you 'she' after a while right?"

I said, "I guess. I mean. Yes. I think I did."

"What do you mean you guess? You don't wear anything from the the men's department. Ever. I saw your room, remember? Girls clothes all over floor."

"Okay. yeah. But the whole baby thing..."

"I treated you like who you are. No, you're nothing like a man. But you weren't much of a woman either. Crying like a baby when I stuck a little plug in your pussy."

That was my Halloween. And it was a crazy, awesome experience.