Hot Tub Surprise

Terra was my girlfriend, a woman really, and she was awesome. She had great facial features with high cheek bones and big brown doe eyes. She shaved her pussy regularly and never sprouted anything longer than fine spikey stubble. She wore stylish clothes and cool shoes. She styled her hair in short blond spikes. Most importantly, Terra was fun to be around when we weren't fucking, which was, of course, the vast majority of the time we spent together. She was kind, assertive, intuitive, fiercely intelligent, and had a wicked sense of humor.

Terra didn't have a perfect body, but I loved it anyway. I admit a more superficial side of me found her curviness a bit of a turn off earlier on in the relationship. However, Terra was great in bed, and with time I began to associate her imperfections with sexual gratification. Her big sloppy and saggy tits frequently got splatted with my cum. Her wide plump ass was a nice soft cushion for hard doggy style action. The subtle but noticeable cellulite on her thighs would jiggle a bit when she spread her legs wide for deep penetration. The soft rolls above her mons served as a reminder of some of her naughtiest dirty talk. "You want to pull your cock out of my pussy and fill my up belly button with your cum, don't you? You think you can do it? You think your load is big enough?" (It was).

The fact that Terra didn't look like a woman in a magazine didn't bother me any longer. As I approached middle aged I began to take solace in the fact that I had matured as a person and could see beauty in another's imperfections. I also came to realize that with air brushing and digital alteration not even the women in magazines really looked like the women in magazines. Or so I thought.

Then I met Terra's friend Jadis. Jadis really did look like a woman in a magazine. Her skin was pale and flawless. Her face was chiseled and well defined with a few scattered freckles and small but piercing grey eyes crowed by sharp well-manicured brows. She had a generous mouth with fine lips, but a small jaw and chin. Her body was thin but taught, muscular, and well defined. Her ass was tight and her hips narrow. Her tits were small, but in a super model sort of way. It was hard not to stare at Jadis and undress her in my mind, but I tried to resist. I didn't want my attraction to Jadis to create conflict with Terra. Evidently my gawking wasn't always very subtle.

Terra took the head of my cock out of her mouth and stroked my shaft vigorously in her hand. "I saw you staring at Jadis's ass today after lunch?" she said.

"No," I stammered, "I was just—" I didn't want to lie to Terra. "Yeah, I saw her ass."

"More like you studied it."

"Well, yeah, okay. I suppose I did more than just look at it."

"That's okay. You can stare at Jadis all you want."

"You're not mad at me?"

"No."

"Why not?"

"Because I know you're mine, no matter who you look at."

"That I am." I agreed.

Terra put my cock back in her mouth and tried to take me down her throat. She got further than her last deep throat attempt but still came far short of balls deep. Gagging she pulled her head back. A trail of spittle streamed in the space from the tip of her lips to the end of my cock.

"Man, I just can't do it." she said. "I have too much of a gag reflex."

"Don't worry about it." I said. The effort was much appreciated. "You don't ever have to try that again. I know it's uncomfortable for you."

"But I want to."

"Why? I never ask for it."

"I want to be the best fuck of your life."

"You already are the best fuck of my life."

"Still, I want to be an ever better fuck."

"Why?"

"So I can outcompete woman like Jadis."

The comment was unexpected. Apparently, the conflict was unresolved. The moment ruined, my cock started to soften and droop.

"Look, I am sorry, Terra. I should have been more sensitive. I won't gawk at Jadis anymore. I promise."

"I suppose you can't help it. Jadis is a very attractive woman."

"Can we move on, or talk about something else?"

"Yeah okay." Terra studies my flaccid penis and sighed. "I suppose I shouldn't leave you with a limp dick."

Terra stroked the skin behind my balls. The tip of one of her fingers brushed lightly against the front of my asshole by mistake. My cock stiffened instantly.

"Oh, you like that don't you?" She put her lips around the head of my cock and slurped noisily. She reached again behind my balls and this time rather deliberately started to caress my asshole.

"That feels so good." I moaned.

"Interesting." Terra said with an impish smile, jerking me slowly. With her other hand, she reached down between her legs and started to stroke her pussy up and down, up and down. Her meaty pussy lips began to swell and glisten with wetness. She gripped and pulled at her giant clit with two fingers. I loved to watch her masturbate. I could feel the pressure of fluids building up inside me.

Terra took her eyes off my cock and looked up at me quizzically, "I have a question for you?"

"Yeah okay," I said, hoping it had nothing to do with Jadis.

"When you were with any of your former girlfriends, did you ever try pegging?"

"You mean let them ass fuck me with a strap-on?"

"Uh huh?"

"No, I've never tried it."

"Do you think you would have let them try it, if they asked?" Terra had a roundabout way of asking for things, testing the waters with a hypothetical situation before making a direct request. I was quite happy to play along.

"That would depend on conditions." My cock remained firm as Terra continued to stoke the both of us.

"Under what conditions would you find pegging acceptable?"

"Well first, it would have to be entirely about sexual gratification for the woman, and not some weird power or control thing. Second, she'd have to start slow and use plenty of lube."

"That makes sense. What else?"

"Ideally the dildo wouldn't be too big."

"Yeah, okay."

"Lastly she would have to be willing to reciprocate?"

"What do you mean?"

"She'd have to agree to take it up the ass herself."

"I suppose that's only fair." Terra conceded. She let go of my cock and began to caress my asshole again. The terms acceptable Terra asked, "so I can peg you then?"

"Yes you can peg me." I said. "I know you don't have weird issues with power or control."

"You don't think it's gay, taking it up the ass?"

I thought this over for a while. "Perhaps it is."

"So you're kind of gay then?"

"I don't think so. I don't have anything against gay people. I think that anybody, straight, gay, bi or whatever should be free to stick whatever they want up whatever orifice they choose. I don't find other men attractive so I guess that means I'm not gay. If you want to bend me over and ass fuck me, Terra, I am all yours."

Terra glanced over at the drawer where she kept lube, condoms (which we quit using long ago), cock rings, and other sex toys.

"Do you have a strap-on in there?" I asked, curiosly.

"No, but I have a vibrator. It doesn't have a flared end so it could get lost up your ass. Then we'd have to go to the emergency room, which would be kind of embarrassing. I know where I can get a suitable phallus for next time."

"Perhaps next time." I agreed. Postponing the deed a few days was a bit of a relief as I need time to prepare myself mentally.

"I suppose in the meantime we will just have to improvise." Terra took her hand out of her meaty pussy and plunged two of her juicy wet fingers up my asshole. The move was quite abrupt and completely took me by surprise. Nothing had ever been up my ass before. The pain was searing, tearing, and intense. I almost shrieked.

"Relax." Terra said soothingly, "Relax." She kept her fingers still and the spasm of my tight asshole eventually slackened. She pulled forward gently against my prostate which hurt a little.

"Ouch," I said.

"Do you want me to stop?"

"No, I guess it's all right."

"I'll be more gentle."

She rocked her fingers back in forth inside me, taking short gentle stokes. Eventually the pain subsided, and I began to experience a deep intense pleasure. Terra seemed to be stimulating my entire body.

"You like that, don't you?"

"I do," I moaned.

"Say, you're a gay boy."

"I'm not gay." I protested feebly.

"Say you're a gay boy, or I'll stop."

"I'm a gay boy."

"Say you love it up the ass."

"I like it up the ass."

"Do you like it or love it?"

"I love it."

Despite being unattended, my cock was engorged, the veins bulging. Twitching involuntarily, my cock seemed much bigger than usual. I knew I wasn't going to last much longer.

"Say, you want a big thick cock up your ass."

"I want a big thick cock up my ass."

"That didn't sound very convincing." Terra said sternly. "Beg for it!"

"Please, please, stick a big thick cock up my ass!"

Terra's tone became less domineering. Quite softly she said, "you know, Jadis thinks you're hot." Perhaps Terra was mocking me, or teasing me, or testing me, but I felt so good I just didn't care. I imagined this is what heroine must be like. The rest of the universe just didn't seem to matter. I would do anything Terra said to keep the pleasure going. "You know, Jadis wants to deep throat you, and then she wants you to bend her over and fuck her up the ass." Terra said slyly. This was too much. On cue I came all over Terra, jet after jet of sticky seamen spraying her, splattering her face and tits, dripping off her nipples, covering her face and getting in her hair.

"Oh my God, so much cum!" she said, "that's the biggest load I've ever seen!"

Meekly, all I could utter was a faint, "uh huh." Even though my asshole stung a bit, I felt so relaxed. All I wanted to do was lie down and go to sleep. Terra fetched a towel from the bathroom and cleaned herself off. She let me relax for a while, but then shook me firmly before I nodded off. "I haven't gotten off yet," Terra said half-jokingly, half-seriously. "You better get to work."

My stupor and lethargy eventually lifted, but my cock remained completely useless. It shrank to the smallest size I can remember since puberty and didn't so much as even wince with the slightest amount of turgor. Like a good boyfriend I got on my hands and knees and licked her giant clit and meaty pussy lips. As usual she was really into getting oral, moaning and pinching her nipples, but I wanted to do something special in return for the pleasure she had given me. After she recovered from her first orgasm I kissed her puckering asshole and probed her anus with my tongue. Terra arched her back, and screamed, "I'm cumming!"

***

We were both busy with work over the next week and didn't really see each other. We made plans on the phone and exchanged the usual pleasantries, but the subject of Jadis, pegging, and anal play never came up. As the days went by, I accepted Terra's comments about Jadis wanting me as mere dirty talk (but very effective dirty talk at that).

When we finally did make plans to get together, Terra insisted Jadis be included, stating she had been so busy she was falling behind in keeping up with friends. She reassured me that Jadis would leave early so that we could spend some quality time together, which was her euphemism for sex. In the end we decided to host dinner at Terra's house. Jadis brought over a pricy bottle of gewürztraminer. I wasn't certain if my attraction to Jadis still had the potential to cause conflict, so I decided to interact with her as little as possible. I volunteered to cook and deliberately caused delays. That way I'd have a reason to be preoccupied and could leave the two ladies to entertain themselves. Bored and somewhat impatient, they broke into the bottle early and, with empty stomachs, quickly got trashed. They would snigger every time I leaned forward onto the counter, and at times I could hear whispers of "rim job," "cock," and "orgasm" punctuated by frequent paroxysms of giggling.

When dinner was finally served, they were so hungry they gobbled it down quickly and hardly talked at all. Jadis muttered something about a good meal, which I acknowledged with the slightest nod on my head. Apparently the gesture was overlooked.

"What is up with your guy?" Jadis snapped. "He's been so rude to me all evening."

"What are you talking about?" I said defensively, "I haven't said anything rude."

"Rudeness isn't just what you say. You won't talk to me. You won't make eye contact with me. You won't even acknowledge that I'm in the room."

"Oh, he's just trying to hide the fact that he thinks you're hot." Terra said dismissively.

"But everyone here already knows he thinks I'm hot. You've told me as much," Jadis said.

I felt pretty embarrassed. To soothe me Terra stroked my hair as if I were a pet. "Be nice to Jadis," she said softly and somewhat mockingly. "She's testy because she hasn't had sex in months."

"Really?" I asked.

Jadis turned bright red, confirming Terra spoke the truth.

"I could see how guys would find her intimidating and wouldn't ask her out."

"Yes, there's that." Terra confirmed, "but there are other reasons as well."

"Can we please not talk about this." Jadis begged.

"Okay, okay." Terra said, conciliatorily. There was a long awkward silence, which Terra interrupted by leaving the table and fetching an inexpensive bottle of Beaujolais nouveau from the pantry. She popped out the cork and suggested we adjourn to the hot tub. I explained I'd join the party after I cleaned up a bit. Jadis excused herself to pee. With Jadis gone, Terra smirked.

"What?" I said.

"I'll be right back." She left for her bedroom, but came back quickly holding a small red bag. "I've got some goodies for later." She explained, unzipping it. She took out a strap-on still in its packaging. "Are you still up for this?" she asked.

The dildo didn't look too big or intimidating. "Sure," I said. Terra grinned. "What else do you have in there?" I asked.

"Oh I just dumped all my sex paraphernalia in there." she explained. "I also got a butt plug and a new bottle of lube. Oh yes, and this," she said, taking out a small orange pill bottle. She unscrewed the top and dumped two small blue diamond shaped pills on the table.

"I don't need Viagra," I protested. "I'm not that old yet. I don't have problems getting it up?"

Terra smiled, "we have big expectations for tonight." She explained. "And it won't just make your dick hard."

"What else does it do?"

"You'll see." Terra said mischievously.

The toilet flushed. Terra shoved the wine bottle in my hand. "Take one quick," she said, quickly stashing the strap-on into the red bag. "No, just one, or your dick will turn black and fall off." As I swallowed the pill, Terra added, "tell Jadis I'm in the hot tub." She scampered off in a hurry, not realizing she was still holding the red bag.

Jadis came out of the bathroom, drying her hands on her pants. "Are you drinking straight from the bottle?" she asked. "That is so gross. You'll give us all your germs." Her tone wasn't really serious. She noticed the remaining pill on the table. "Is that an oxy?" Before I could answer she popped the pill into her mouth, snatched the bottle from my hand, and washed it down, drinking straight from the bottle.

"No, that's Viagra." I explained.

"Oh, do we have plans for this evening?" Jadis said mockingly, "Worried you won't be able to get it up?"

I ignored the comment. "Shouldn't do you any harm. Only works on men."

Jadis shrugged and asked about Terra's whereabouts. I directed to the hot tub out back. Jadis took the bottle with her. I loaded the dishwasher. Over the clanging of the knives and forks I could hear Jadis say, "hey, you're naked!"

"No clothes allowed in the hot tub," Terra said. "That's the only rule."

No matter how hard I scrubbed, I just couldn't seem to remove some of the sauce that had burnt onto the edges of the largest pan. The back yard was quiet, there was no murmur of conversation, just the bubbling sound of hot water. Eventually Terra yelled, somewhat impatiently, "you're not being very social. You're keeping us waiting."

Frustrated, I decided to soak the pan and come back to it later. I joined the ladies out back. They sat next to each other, fleshy and visible above the waterline from the waist up. Jadis had small but firm tits with small areolas that extended only slightly beyond the root of her nipples. Terra's lip stick had been smeared, and Jadis had similarly colored smudges all over her cheeks and mouth. The two had been making out. I knew Terra had been with women before, so I was neither shocked nor alarmed. The bottle on the ledge between the two women was almost empty. The red bag sat all by itself by the wall in the corner, sad and neglected.

"You like what you see?" Jadis asked. Her arms and shoulders were slender but muscular and well defined. Her stomach was flat with faint but visible contours of abs. She probably did crossfit or something.

"I do," I said, "very much so." There was no point in playing coy.

"Stop gawking and strip," Terra commanded. "No clothes allowed in the hot tub!"

I took my shirt off, folded it, and placed it on one of Terra's patio chairs.

"Not bad," said Jadis, "not bad at all. I like a shaved chest. I can tell he works out."

"Now take your pants off." Terra commanded. "Turn around and show us your ass." I gladly complied. "Now the underwear."

"That's a pretty fine ass." said Jadis.

"Now turn back around and show us your cock and balls." Terra said.

"What the fuck is that?" Jadis said indignantly. "I thought you said he was the perfect male specimen. That's barely bigger than my pink finger!"

If I had heard such a comment during my college days, I would have been mortified. However, I had been with a lot of women, and no one had ever seemed to complain. I had learned to be secure with what I had. As it was that evening, I felt very much like the kid in elementary school who ate paste. Any attention from these two hot naked women was good attention, even if they were poking fun at my junk.

"Oh it does look pretty puny." Terra agreed. "But it's cold out. It's very much a grower. Once it gets warmed up in the hot water it will seem much bigger."

I took my place in the hot tub, sitting close to Terra. After a few minutes Terra said, "okay, you should be nice and warm now. Stand up, show Jadis your dick again."

"Oh, that's still pretty small."

"Well, it's still limp," Terra said defensively. "Come on now, jerk your dick, show us how big you can get."

Eager to please, I quickly obtained a semi-rigid state.

"Okay, that's not tiny," Jadis said, "but it's still on the small side."

"It's six inches," Terra said.

"Just because he says it's six inches, doesn't make it true. Most guys lie about the size of their dicks. I bet he barely has five."

"I'm pretty sure, it's six inches. When I hold it in my hand it seems like six inches."

"Ever measure it?"

"No, but that's not a bad idea." Terra got out of the hot tub to go find a measuring device. Wet and eager to get out of the cold air she ran quickly. Her ass jiggled.

"Terra has a big ass." Jadis said crassly.

"She does," I agreed. "But I just want to bury my face in it, and judging by the fact that her lipstick is smeared all over your face, I bet you want that ass too."

Jadis blushed. "I didn't mean it in a bad way."

Apparently Terra had trouble finding what she was looking for, because it seemed to take her forever. I just sat there, taking in the clear skies and observing the first stars of the evening. Jadis eventually broke the silence, "you like my tits?"

"I do like your tits."

"But you like Terra's better. Don't you? They're so much bigger and fuller."