The Double Date

Josh and I talk on the way home from work about everything. He has been telling me about this girl he met at lunch by accident and then having planned their lunch breaks together. I asked if he got lucky yet. He slowed his response and said he was not so sure about next steps with her. He said she was really pretty, sexy, funny, easy to talk with, and they had so much in common.

"Okay. So when are you going on a real date? She sounds fantastic!" I asked excitedly.

"Well, Pete, there is one catch. I am not sure how you are going to take it and don't make fun of me." Josh said, shaking his head slowly as he contemplated his next words.

"Never, would I make fun of you!" I replied, trying to put him at ease. "Is she married? Got a scar in a weird place? I am sure it is nothing you two can't figure out."

"There is nothing like that. She is different." He paused, "She is packing." He finally blurted.

"Wow! That is something you don't hear every day. How did you find out if you didn't try?" I teased.

"She told me on our third lunch date. She wanted to be up front about it." He tried to keep this conversation serious.

"Hmm. Pretty, funny, and she is honest. She sounds great. How many lunch dates have you had?" I asked.

"Five." He answered sheepishly.

"Well, there is definitely some connection between you two-even after she told you. I think you should take the next step. I don't see an issue and I don't think anyone else would." I assured him.

"What would you do?" He asked, looking directly at me, as if challenging me.

"Well, I don't know. However, if she is as perfect as she says, I would definitely consider the possibility. It is new and all but a connection is a connection. You can't let a few inches get in the way." I added kiddingly.

He seemed quite relieved, ignoring my insensitive joke. "I am really glad you feel that way! She and I did talk about a date, though she knows I am hesitant about the next step. So, she offered a solution!"

"I am intrigued. What is her plan?" I inquired.

"She suggested a double date with you and her roommate tomorrow night!" He exclaimed.

"Huh?" My mind whirled with confusion.

"Sure! Her roommate is single and she is into it." He replied, almost jokingly.

"And, of course, she is also special?" I stammer.

He responded, almost mockingly. "Yeah, but, as you said, that should not matter." He laughed, knowing he cornered me.

My friend and I are in our late twenties, early thirties, and not dating anyone. I was not busy on Friday but definitely nervous or excited about this double date. Was the girl pretty? Was she fun? Did it matter? Why did I care? I would be there for support only. Therefore, it would not matter about the roommate. Or would it? What if I found her to be pretty, attractive, and great to know? What would I do then?

Nah, I reasoned. She will look like a he. I will be turned off and I will jus t be his friend; helping him score with his intriguing woman. The last thing he needs is someone to shame him when he might be with someone special; regardless of her extra parts.

"Um, ok." I slowly replied.

"I will check with her at lunch tomorrow but I knew you would be cool with it."

"Can you tell me anything about her roommate? What have you told her about me?" I asked nervously.

Patting me on the shoulder, he replied, seemingly quite relieved, "We have not discussed details. You two are just there to help us. Does it matter? Are you worried or do you want her to like you?" He laughed as he elbowed me lightly in the ribs.

"Are you into it?" He chided.

Quickly, I replied, "What? Me? No. I am just saying. I don't want to go to a restaurant with someone not pretty or something. I am your friend but there are limits!" I laughed.

"Don't worry, Pete. She told me her roomy was pretty, fun, and very out-going. You two will get along well, she assured me." He smiled confidently.

"Josh, what the heck did you say about me?" I replied, almost scared for some odd reason.

"I did not say much." He replied evenly. "Though, I did say you were adventurous and open minded."

"Ah man. This is a lot to take in. I want to support you but this is big. I was not ready for it." I said, shaking my head.

"If you want to back out, I understand." He said kind of dejectedly.

"No. No. I will do it." I replied quickly. "I want you to be happy. I think you are awesome to have a positive and adult attitude about your lunch friend. Set it up. I am good." I shook his shoulder for support and solidarity.

He smiled cautiously and perhaps happily. "Are you sure you are not going to back out on me?"

"There is no way. Count me in." I smiled assuredly. "Let me know tomorrow how lunch with her goes. I am rooting for you, buddy. Remember to disregard the haters. You never know." I reassured him.

The next day, Friday, we hooked up for our usual ride home from work.

"How did it go?" I eagerly asked him.

"Great! She is excited about tonight. You are still in, right?" He asked expectedly.

"Yeah. Sure. I am willing to help you." I responded nonchalantly.

"Cool. She told her roommate about you and our date. They are both excited. She can't wait to meet you." He replied excitedly.

I really wanted to ask for a picture but I figured that would be too shallow a request. What if his girl is not pretty or sexy? What if my 'date' looked like, a guy, or someone who is not exactly-womanly? However, I figured I am there for him and if the chips fall badly, they fall; I reasoned.

We agreed I would meet him at his place and we would drive over with liquor and flowers. The four of us would chat for a bit, go to the restaurant, have dinner and then part. He would have his date and that would be the end.

The truth is told, though; I did some 'research' last night about transsexuals and transvestites. Some of them looked great but others; not so much. I watched guys sucking and swallowing the special women. I watched the gurls go down on their guys. I watched cum shots and ass fucking and I have to admit I came more than once. The good ones were beautiful, sexy, hot, and wow! The bad ones were still hot by the way they moved, what they wore, and their adventurousness. There were so many thoughts running through my mind as I worked my way to his apartment that night.

I arrived at his place about 9 pm and I brought two bouquets of flowers. We drove in his car to the liquor store to get beer and wine, so we can get to know each other before going to dinner.

Driving over to the girls' apartment, he was incredibly nervous and making apologies for this double date. I assured him nothing was wrong and simply stated, let's see what happens. Of course, I was wishing him well and telling him nothing would go wrong and his girl would be great.

"Relax." I told him. "Just be yourself and be comfortable talking with her and being in her company. I am not judging you. I just want you to be happy." I tell him confidently.

"Yeah but what I do about her extra parts? I don't know how to handle that." He asked, almost scared.

"Just take one step at a time. If you like her, things will take their course. Be cool and relaxed." I coaxed him.

We arrived at their place and Josh knocked on the door.

Suzy answered the door and she was prettier than Josh described. She was quite tall, about his height, very lean, and very sexy. Her long blonde hair cascaded down her slender shoulders and her light blue blouse showed impressive cleavage. Suzy's tight black slacks showed her long, lean legs and very shapely ass.

Leading us into their apartment, she introduced us to her roommate, Anne, as we entered their apartment.

Anne was a beautiful brunette and I was pleasantly shocked. Is this a guy or a woman! She wore a buttoned white blouse with a knee length red pleated skirt.

I am sure my look of amazement amused her.

She looked at me and laughed. "What did you expect, Pete, perhaps someone hideous? Some guy in drag, perhaps?"

"You are stunning, Anne! I am sorry. I just did not know who to expect." I say, blushing to no end, handing her the flowers, acting foolishly and embarrassed.

"Don't worry. I am just fucking with you." I think Anne took my ignorance and foolishness in stride as she took the flowers from my trembling hands, with a slight chuckle.

She leaned into me, breathed into my ear, "Thank you handsome," kissing my cheek.

She was so pretty, sexy, and from all perspectives, a very attractive woman. I almost trembled from confusion. Or was it excitement?

After our initial introductions, I think Anne and I hit it off immediately. We did not have the pressure and nothing to lose. Although it was weird to me because I think we had a connection.

Suzy played the perfect hostess and served our drinks as we settled into our respective seats. Suzy and Josh had the love seat while Anne and I were relegated to the couch.

Anne and I laughed and moved closer to each other on the couch as our conversation continued. We chuckled, looking at each other as we watched the couple across from us be cautious and careful of their spacing. During the conversing, we moved closer and closer, continuing eye and physical contact.

At some point, I felt her thigh against mine and I was excited. When she touched my arm or chest, I was getting more and more turned on by her. Touching each other's arm or leg, we would look at each other and smile. Was it lust or curiosity or something else? I don't know but I liked it. I think she did as well.

Perhaps she was teasing me, wondering how far this straight guy was willing to touch her, and perhaps do more with her.

I think my confidence was growing because of her playfulness as she was touching my hair, and at times caressing my arm and chest.

As we continued our small talk, she would touch my arm or side, laughing and looking directly at me. I would respond by touching her arm or leg, lingering a bit, wondering if she would stop me, though she didn't. Rather, she would give me mischievous smiles, as if daring me to go further.

Our faces were closer and closer as different comments were made and the conversation developed to topics more suggestive in nature.

At times, she would move my hand to her hip letting me feel her to her inner thigh, and wondering how far I would be willing to go. Other times, she would pull away, gauging how I would react.

"Have you two kissed yet?" Anne asked the couple across from us, squeezing my upper thigh.

"No." My friend, Josh, stammered. "We have not gone on a date yet."

"Well, now is your opportunity." Anne playfully quipped. "You are officially on a date."

Josh turned and looked into Suzy's eyes but was too shy to move his lips toward hers.

"Dude." I sighed. "She is a beautiful woman. What is the problem?"

I get a hard elbow from Anne.

"What am I, chopped meat?" She playfully scolded me.

"Of course she is not as pretty or sexy as you." I said quickly, moving my face close to hers.

Anne took the opportunity to wrap her arms around my neck. "Shall we show them how it is done?" She purred loud enough for them to hear.

I tentatively moved my lips closer to hers. My hands moved around her waist as she pressed herself against me.

Her lips were so soft and I tasted her cherry lipstick; especially as she opened her lips just enough to slip her tongue through, probing my lips, easing them open more generously than I initially allowed. Our tongues tentatively touched as we slowly invaded each other's mouths. Unhurriedly, our lips pressed and tongues caressed, as we enjoyed the moment.

We slowly broke from each other and looked over at them, expecting similar passion. Unfortunately, they were just looking at us.

My mind was still reeling from the excitement from Anne's touch and kiss as she separated us to look at them.

"Well. Now, it is your turn." Anne stated excitedly while squeezing my hand.

She and I looked at each other as the couple in the love seat seemed to flummox their way through their tentative first kiss.

Quickly breaking that kiss, they said simultaneously. "We need a drink." Josh and Suzy quickly stood and moved to the kitchen.

Taking the opportunity, Anne pulled my face to hers and we continued kissing. My hand was on her hip but she moved it once again to her inner thigh. Taking the hint, I slowly felt my way upward as her fingers playfully danced to my now visible lump. The rustling sounds from Josh and Suzy approaching from the kitchen stopped our continued advancement upon each other.

Suzy chuckled as she passed us, "Seems some people are getting to know each other very well."

I blushed to no end but Anne played it up very playfully, caressing my chest as she answered.

"I may have found a sexy male toy." She replied, looking at me for my reaction.

"I think my world is rapidly widening." I stuttered while staring into Anne's lips and her captivating eyes.

As the cautious couple settled back on the love seat, Anne continued to press them, while squeezing my inner thigh. "Well, you almost have the kissing part in order. What about the touching? Have you touched her, Josh?" She said very suggestively, squeezing her breast through her blouse, while looking at him.

They both blushed and seemed frozen.

Emboldened, I turned to Anne, "Can I touch you? You know, just to show them it is cool and normal?"

She quickly smiled and leaned her chest toward me, while undoing a couple buttons on my shirt so she had easy access to my hair covered chest.

"Are you sure you want to do this? You know, touch me?" She teased while running her fingers through my chest hair.

"Oh yes!" I am sure I said it too quickly but I was very anxious to squeeze those beautiful breasts. I was thinking she is a C-cup but I needed a more hands-on approach to be certain.

I leaned forward, kissing her soft lips again, pressing my palms against her breasts and squeezed gently.

"Hey, Pete," She purred into my ear, breaking the kiss and sliding my hand from her chest to the hem of her skirt. "You can go a little higher now, I think."

I gasped quietly into her ear, squeezing her leg as my fingers ventured upward.

She giggled quietly, and looking into her eyes, I felt he fingers press against mine as I allowed her hand to guide me wherever she wanted it to travel.

I don't know if I was naïve, excited, or just plain horny. However, when I looked down and noticed my hand was suddenly on her generous bulge I was ready for whatever she wanted. She guided my hand under her skirt to slowly outline her excited length with my fingers through her panties.

"Dude! She is excited! And bigger than me, I think!" I exclaimed, rubbing her panties, looking at Josh.

"Still want to play?" She asked me saucily, while caressing my hard on through my slacks.

"That is a lot to swallow." I stammer.

"Is that a promise?" She asked playfully, trapping my hand between her legs before pressing her lips against mine for another deep kiss.

Breaking the kiss and responding trembling, "I did not mean it that way."

"Oh. So, are you just teasing me?" She asked excitedly while slowly rubbing my very hard cock through my pants. "Maybe I should stop?" She purred demurely into my ear.

Pushing her hips upward, she purred. "Don't be shy. I will make you very happy." She promised, kissing my lips and face.

Tasting her soft lips and feeling her hardness through the silk panties, made me more and more excited and more scared.

Anne lithely moved her beautiful body so the back of her was to our audience as she unzipped my pants and lowered them below my hips, pulling out my very hard cock and slowly stroking it.

I looked down at Anne and then to the love seat to see Suzy position herself on the floor, kneeling in front of Josh, his pants at his ankles.

Anne eased my head downward and under her skirt. I parted her clothes and could barely see her large bulge as I parted her panties to the side.

"Don't be shy, sweetheart! Show them how a real man takes care of his woman." She growled as she pushed her hips upward toward my lips.

Her cock was hidden from the couple and my face was concealed under her skirt. My cheeks were pressed tightly within the confines of her legs. I could smell her; feel her excitement, and the heat emanating from her nether regions.

Instinctively, I pushed my tongue outward, tasting what I could. She sighed with excitement and I felt her urgency as she pushed forward, the tip of her cock wanting entry.

She swallowed my cock in her mouth as if to instruct me to my next steps. The pleasure she gave me encouraged me to take the head of her cock between my lips. She took me in deeply and I was too lost in thought to do anything but take her as deep as my throat would allow.

She groaned and moaned while sucking my erect cock, which only emboldened me to take more of her inside my mouth. She humped and I sucked her impressive and hard length deeper and deeper into my face.

I squeezed her ass cheeks and created a tight suction between my lips; trying to please her as much as she was pleasing me.

Her lips were sawing up and down on my dick and I tried to mimic her actions. Her mouth was wet; her tongue playful, and her deep-throating ability was unequalled!

Anne pumped her hips, forcing as much of herself into my mouth as she could with each thrust. She let me rest, then resumed her pushing, then let me rest before she continued to fuck my mouth faster and faster.

Her lips on my cock were like suction cups, trying to siphon the cum from me so she could taste the reward. I tried to mimic her actions, sucking, and swirling my tongue around the head, and sucking more of her shaft into my throat.

Her head bobbing and tight lips were pushing me to my limits. I tried to warn her through my restless movements, since my mouth was filled with her dick. She only increased her tempo and suction.

"Mmmmffffff!" She muffled into my cock as she exploded into my mouth!

Squeezing her ass cheeks, I sucked really hard on her cock as I shot my load into her mouth.

"Mmmm! Fugggghhh!" My orgasmic scream was muffled as I swallowed and swallowed again her spewing cock!

I did not stop sucking Anne after her explosion set me off. I pushed my hips upward and she greedily accepted the last of my orgasm. She sucked the last bit of cum from my cock as if she was drinking nectar.

This woman is amazing! I prayed she was real, as I sucked in her seed as happily and eagerly as any woman I have gone down on before I met this insatiable creature.

I kept her in my mouth until she finished her load and softened between my lips. My cock had long softened; very well spent but she continued to keep me between her lips, humping softly as she kept her tongue caressing my cock head.

The calming did not last long, unfortunately.

"I can't do this." I heard my friend exclaim, rather scared.

A few moments later, I heard clothes rustling, some movement, and a door closing.

I was still buried under Anne's skirt as her beautiful and special gurl part was so soft between my lips. Eventually, or probably more quickly, I had to lift my head upward.

Josh left the apartment.

Suzy was still on her knees. I could see traces of cum across her lips and down her chin as she looked between Anne and me, then chased off to her bedroom, thoroughly embarrassed.

I was barely alert but clearly something went very wrong; which is never good.

Trying to clear my mind after a very intense sexual experience, I turned to Anne.

"What the fuck! What happened? What do I do? Shall we console her?" I babbled.

Anne untangled from me and quickly grabbed my hand, pulling me up from the couch. We kissed each other first, trying to maintain our closeness and passion as we moved, though the matter was urgent. We guzzled our drinks and put ourselves together.